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Vacation Rentals in Chicago, IL

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    All 182 Rentals in Chicago
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    Travellers to Chicago are booking June dates now. Secure your vacation rental today, and have the perfect trip.
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    $425
    / Night
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    1 / 13
    5 of 5 stars (15) Excellent
    Lakeview
    2 Bedrooms / 1 Bathroom / Sleeps 6
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    $219
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    1 / 12
    5 of 5 stars (1) Excellent
    Near North Side
    1 Bedroom / 1 Bathroom / Sleeps 4
    travellers have booked this property
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    $364
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    1 / 13
    4.5 of 5 stars (9) Very good
    Lakeview
    3 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Reviews (9) Make Enquiry
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    $364
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    1 / 27
    5 of 5 stars (4) Excellent
    The Loop
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    travellers have booked this property
    Overview Reviews (4) Make Enquiry
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • ?
    • Wheelchair access
    • Elder access
    About this property
    1 KING SIZE Bed in the masteroom and 1 full size bed in the second and air-mattress available for more than 5 people 1600 square feet Sleeps 6 2 Flatscreen TVs Clean freshly-washed white sheets and white Towels waiting for you. Coffee maker now available. Private garage parking in the... View all property information
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    5 of 5 stars Reviewed 7 November 2014
    The Condo was a great place for rest and relaxation between all the excitement we found in Chicago. Outstanding views of the Chicago skyline, great location, comfortable beds and...
    5 of 5 stars Reviewed 1 August 2014
    We loved the pad, the location, the view, and the city. Would go back to this spot in a heartbeat. The owner was courteous and easy to contact.
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    $273
    / Night
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    1 / 11
    4.5 of 5 stars (3) Very good
    Lakeview
    2 Bedrooms / 1 Bathroom / Sleeps 5
    travellers have booked this property
    Overview Reviews (3) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Internet Access
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Spacious, elegantly appointed and furnished Lakeview vacation/executive two bedroom, one bathroom apartment. First floor on a quiet tree-lined street, the entire apartment features; either oak floors or ceramic tiles, all solid oak doors and windows and oriental rugs. You will find our... View all property information
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    5 of 5 stars Reviewed 4 February 2015
    Good value for the money. We enjoyed the player piano. Beds were comfortable and everything was clean.
    4 of 5 stars Reviewed 28 July 2014
    Close to transit & grocery. Lots of space. Communication with Andy was great. He answered any questions we had before the trip in a timely manner. Easy check in and out...
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    $3,642
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    1 / 22
    Near North Side
    Studio / 1 Bathroom / Sleeps 2
    Overview Make Enquiry
    Amenities & Details
    • Dishwasher
    • Internet Access
    • Shared Outdoor Pool...
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Amazing unit features wall to wall cherry hardwood floors, stunning kitchen with quartz countertops and snaidero cabinetry, loads of storage space with professionally organized closets, floor to ceiling windows exposing great Chicago River and city skyline views, beautifully updated marble... View all property information
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    $546
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    1 / 13
    5 of 5 stars (2) Excellent
    Near North Side
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    travellers have booked this property
    Overview Reviews (2) Make Enquiry
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    Located a block north of the Chicago River this property features a prime location just steps from Michigan Avenue. Amenities include gym, pool, and hot tub. Two queen size beds and a fold out sleeper sofa make it possible to sleep six. Chicago's premier downtown Streeterville neighborhood grants... View all property information
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    5 of 5 stars Reviewed 28 March 2015
    This place is wonderful. Clean, quiet, trendy and well appointed. My family and I really enjoyed our stay.
    5 of 5 stars Reviewed 28 January 2015
    My fiancé and I really enjoyed ourselves here!! It was everything we were looking for in a nice condo for a mini getaway. We walked right out our condo and BOOM there was...
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    $243
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    1 / 8
    4.5 of 5 stars (2) Very good
    Northwest Side
    2 Bedrooms / 2 Bathrooms / Sleeps 5
    travellers have booked this property
    Overview Reviews (2) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dryer
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    This very affordable two bedroom, two bathroom apartment can sleep up to six guests. There are queen sized beds in each bedroom and a pull out couch in the living room. With features including: a breakfast table in the well-appointed kitchen; dining room; comfortable living room; a balcony;... View all property information
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    5 of 5 stars Reviewed 17 August 2014
    Nice apartment for up to 6 people, around $20 taxi ride from the Airport. Close to a large park, bus, and train stations. We purchased 7 days CTS passes for $33 each with...
    4 of 5 stars Reviewed 29 March 2014
    Bed was a little uncomfortable and broke often. Parking was difficult. Clean apartment, ideal for a large family
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    $242
    / Night
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    1 / 9
    1 Bedroom / 2 Bathrooms / Sleeps 4
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Gym
    • Internet Access
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    About this property
    The 400 North LaSalle Luxury Residences offer one of the highest standards of quality finishes found in a Chicago development. The quality and craftsmanship of each home is in keeping with the contemporary style of 400 North LaSalle, and residents will find that their homes are fitted with standard... View all property information
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    $115
    / Night
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    1 / 10
    5 of 5 stars (1) Excellent
    Lakeview
    1 Bedroom / 1 Bathroom / Sleeps 2
    travellers have booked this property
    Overview Reviews (1) Make Enquiry
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    This is a beautiful garden unit. It comes fully furnished with a queen size bed plus a pull-out couch. Plenty of sitting room, updated bathroom, does not have kitchen but does have small fridge, microwave and coffee maker. The location is ideal, being close to the city and still in a quiet... View all property information
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    5 of 5 stars Reviewed 13 October 2014
    My wife and I spent 3 night here in Sept 2014. The owner was very friendly and helpful. This studio is located in a nice quiet neighborhood, close to restaurants and shops, and...
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    $181
    / Night
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    1 / 10
    4.5 of 5 stars (2) Very good
    3 Bedrooms / 1 Bathroom / Sleeps 8
    travellers have booked this property
    Overview Reviews (2) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dryer
    • Housekeeping...
    • Internet Access
    • Safe
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    This is a 3 Bed Room apartment of a two flat brick building in Andersonville area of Chicago. This apt has: 3 bedrooms, sleeps 8 Air Conditioners Free cell phone for international guests (plus deposit) Eat-in Kitchen Living Room Full size fridge Free parking Free laundry Complete kitchen Living... View all property information
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    4 of 5 stars Reviewed 10 July 2014
    I really enjoyed staying here. A great property. The sink did break while we were there but Jackie was right on getting it fixed for us! Great place, big enough for our group!
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    $120
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    1 / 14
    5 of 5 stars (10) Excellent
    Northwest Side
    2 Bedrooms / 1 Bathroom / Sleeps 4
    travellers have booked this property
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    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dryer
    • Fireplace
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    This is a nice place on a quiet street, close to transportation and many restaurants. Very close to I 94. View all property information
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    4 of 5 stars Reviewed 9 April 2015
    My husband, my daughter and I stayed here while apartment hunting for my daughter. We were able to find street parking easily in front (parking sticker is provided). The WIFI was...
    5 of 5 stars Reviewed 2 March 2015
    I really thank god i found this place. I had my family in from out of town and this was great. Hanna & her husband was very nice & helpful, anything we needed they accomodated us...
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    $237
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    1 / 15
    5 of 5 stars (2) Excellent
    Lakeview
    2 Bedrooms / 1 Bathroom / Sleeps 6
    travellers have booked this property
    Overview Reviews (2) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    • Waterfront
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    Our vintage apartment is located in the beautiful Chicago neighborhood of Lakeview with many ethnic restaurants and clubs with-in walking distance. Try a different ethnic specialty every night of the week. The apartment is in an ideal location to come and explore Chicago. Stroll 2 blocks through... View all property information
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    $591
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    1 / 15
    5 of 5 stars (15) Excellent
    3 Bedrooms / 1 Bathroom / Sleeps 6
    Overview Reviews (15) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Fireplace
    • Grill
    • Hot Tub
    • Internet Access
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    Book Now for ALL INCLUSIVE BUDGET PACKAGE at a unique and beautifully decorated Bed & Breakfast inn. Stay on our third floor apartment with a shared bath and accommodations for up to 6-9 travelers - Full Size Refrigerator, Huge Leather Couch, Dinette Set, Massage Chair, Air Hockey Table and so... View all property information
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    5 of 5 stars Reviewed 13 April 2013
    We were visiting Chicago for accepted students' visit days at University of Chicago and wanted to stay somewhere close to the university that wasn't a Ramada Inn type hotel...
    4 of 5 stars Reviewed 7 December 2012
    We enjoyed our stay at Welcome Inn Manor B and B. Mel and his assistant were very hospitable, and always started our day off with a hearty and tasty breakfast. Mel is at the ready...
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    $176
    / Night
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    1 / 12
    1 Bedroom / 1 Bathroom / Sleeps 2
    travellers have booked this property
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Gym
    • Pool Table
    • Safe
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • Wheelchair access
    • Elder access
    About this property
    This Cozy Studio is in the heart of the prestigious River North neighborhood in downtown Chicago. The new 50 story high rise is surrounded with great shopping, numerous restaurants and exciting night life. Getting anywhere is easy because building located few blocks away from the CTA-Grand Red Line... View all property information
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    $149
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    1 / 14
    4 of 5 stars (2) Very good
    3 Bedrooms / 1 Bathroom / Sleeps 8
    travellers have booked this property
    Overview Reviews (2) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dryer
    • Garden
    • Internet Access
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Welcome! Welcome! Our single family brick house is located in a rare semi-private block about 5 miles West of Downtown. It has 3 Bedrooms, 1 Bathroom, Living Room, Dining Room and Full Kitchen. If you enjoy a quiet home with newer beds, clean sheets and towels, spaces, privacy, kitchen, laundry,... View all property information
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    5 of 5 stars Reviewed 18 July 2014
    Nice location. Everyone got their own beds. Easy to downtown. Kitchen and free laundry. Free Tide detergent too (not expected). Will stay again.
    3 of 5 stars Reviewed 7 May 2014
    The location of this property was great. It was about 12-15 minutes from downtown, which is where we wanted to be. There was plenty of on-street parking right in front of the...
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    $97
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    1 / 14
    4.5 of 5 stars (3) Very good
    Studio / 1 Bathroom / Sleeps 2
    travellers have booked this property
    Overview Reviews (3) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dryer
    • Internet Access
    • Washer
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    About this property
    Furnished Studio. Double bed, full bath, and full kitchen. Unique location. You don't need a car living here. Plenty of transit options. A couple of blocks to Red line train station. Direct express bus to Chicago downtown stops right around the corner. 20 minutes to the city center by public... View all property information
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    4 of 5 stars Reviewed 3 September 2014
    Great stay, close to the El train and cheaper than a hotel! Able to stay parked out front for free and take the El where ever we wanted to. If you want a great stuffed pizza...
    5 of 5 stars Reviewed 8 July 2014
    the location of the apartment we stayed was convenient enough:only some min away from the red line train and a min from the bus stop,so getting to downtown is easy.we got a great...
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    $278
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    1 / 11
    5 of 5 stars (1) Excellent
    Roscoe Village
    2 Bedrooms / 1 Bathroom / Sleeps 6
    travellers have booked this property
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Make our apartment the perfect home base for your family vacation or romantic getaway to Chicago. There is plenty of room to spread out and enjoy yourselves. The house is beautifully furnished and stocked with all of the essentials. The apartment is an easy walk to multiple bus and train lines,... View all property information
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    5 of 5 stars Reviewed 25 September 2014
    My wife and I travel to Chicago 4-6 times per year to visit our daughter and her family. We usually stay with her but this time she hosted her sister and their family which made...
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    $182
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    1 / 7
    4 of 5 stars (5) Very good
    Lincoln Park
    1 Bedroom / 1 Bathroom / Sleeps 3
    travellers have booked this property
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    Amenities & Details
    • Air Conditioning
    • Internet Access
    • Safe
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    Wireless Internet Flat Screen TV in bedroom and living room Cable Clean sheets and towels Silverware, pots & pans Very large bedroom and living room Wall unit AC's in bedroom and living room Washer & Dryer is downstairs on first floor This is an ideal location for visitors. Nice restaurants... View all property information
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    5 of 5 stars Reviewed 1 April 2015
    Jonathan was responsive before the trip, generally thoughtful, and also accommodating about our bags (allowed us to bring them before check-in, and it turned out that the next...
    2 of 5 stars Reviewed 10 March 2015
    Booked this apartment for a family of three, husband wife and infant (8 months old) Owner cancelled our reservation because it was only booked for two adults, owner advised an...
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    $472
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    1 / 30
    5 of 5 stars (1) Excellent
    Lakeview
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Safe
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    CHICAGO GUEST HOUSE Tripadvisor Certificate of Excellence 2014 5.0 of 5 stars --133 Reviews Ranked #1 of 51 Specialty Lodging in Chicago! Walk in to the home and the first thing you notice is nothing has been taken for granted. You'll be engulfed in warm inviting hues. The beauty & integrity of... View all property information
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    5 of 5 stars Reviewed 28 April 2015
    I traveled to Chicago for a Baptism, meeting family from LA and Boston. We stayed in the Lakeview suite. Teri allowed us to enter the apt. early on the day of our arrival. The...
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    $121
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    1 / 17
    5 of 5 stars (1) Excellent
    Northwest Side
    2 Bedrooms / 1 Bathroom / Sleeps 4
    travellers have booked this property
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Washer
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • Wheelchair access
    • Elder access
    • ?
    About this property
    1100 sq feet of your own space! Lots of room to stretch out here, two bedrooms with queen-sized beds, an office, living room, den, full kitchen, one bathroom, laundry in unit, back deck, backyard with apple tree (apples!!!), Keurig coffee maker, and parking right out front! Queen sized air... View all property information
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    5 of 5 stars Reviewed 8 February 2015
    This is a two bedroom apartment on the first floor on a quiet street two blocks from Humboldt Park. We arrive in two days after the big blizzard, and the sidewalk was nicely...
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    1 / 40
    4.5 of 5 stars (6) Very good
    The Loop
    Studio / 1 Bathroom / Sleeps 2
    travellers have booked this property
    Overview Reviews (6) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Gym
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • Wheelchair access
    • Elder access
    About this property
    888.761.RENT or 312.242.1625 215 W. Washington St. Chicago, IL. 60606 (Washington/Wells in the Loop in Downtown Chicago - Five Blocks West of Michigan Avenue and Millenium Park 'Bean'; In Business/Theater District) Check Availability and Book Online Now: http://reservation.worldweb.com/hotel/1278... View all property information
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    5 of 5 stars Reviewed 19 July 2014
    Beautiful furnished apartments with kitchennete and in the heart of downtown, just a few blocks away from State st and michigan ave. I had a very pleasant and comfortable stay...
    5 of 5 stars Reviewed 7 May 2014
    The location is so convenient, the blue line train from O'hare airport takes you right to the stop of which is about 5 minutes walk to the building. The unit is clean and with...
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    1 / 13
    5 of 5 stars (1) Excellent
    Lakeview
    1 Bedroom / 1 Bathroom / Sleeps 4
    travellers have booked this property
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    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Internet Access
    • Safe
    • Washer
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    This beautifully updated 1 Bedroom, 1 Bathroom loft in Lakeview has all you'll need during your stay in Chicago! Conveniently located only 1 block from the lake shore, only 3 blocks from Wrigley Field, & close downtown, shopping, dining and more! Lakeview is one of the hearts of Chicago. The unit... View all property information
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    5 of 5 stars Reviewed 10 April 2015
    Beautifully decorated with a nice location for the baseball game. The owner Lisa, does an excellent job communicating . I look forward to staying again.
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    1 / 22
    5 of 5 stars (4) Excellent
    Near North Side
    1 Bedroom / 1 Bathroom / Sleeps 1
    travellers have booked this property
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    Amenities & Details
    • Air Conditioning
    • Balcony
    • Gym
    • Internet Access
    • Satellite TV
    • Washer
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    Stunning views overlooking the city skyline and the Chicago River. Located on the Chicago Riverwalk and walking distance to the lakepath, Ohio Street Beach, Navy Pier, 'Magnificent Mile' shopping, the loop, Museum of Contemporary Art, Millennium Park and Grant Park. Close to public transit. Taxi... View all property information
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    5 of 5 stars Reviewed 6 November 2013
    Oxana was a good host, helpful but unobtrusive. Unit was very good and additional facilities were available in the building (gym, laundry, extra rooms to relax, outdoor area...
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    $140
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    1 / 18
    Lincoln Square
    1 Bedroom / 1 Bathroom / Sleeps 2
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Internet Access
    • Safe
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    I live here, but travel frequently! My apartment is a vintage Chicago Brownstone in the trendy, upscale Andersonville Area. It's close to shopping, nightlife, transportation and everything all the cool kids want to see and do! :-) I live on a quiet and very safe street that's easy to access from... View all property information
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    $157
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    1 / 20
    4.5 of 5 stars (4) Very good
    1 Bedroom / 1 Bathroom / Sleeps 6
    travellers have booked this property
    Overview Reviews (4) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Internet Access
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    About this property
    Plenty of free street parking is available on our block. This is the first floor of our home so we expect all guests to be QUIET & respectful. If you love to party, stomp around and yell then this is not the place for you. No parties, no loud music & no stumbling in drunk at 2 am. We are old &... View all property information
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    4 of 5 stars Reviewed 3 September 2014
    This was my first experience using Trip Advisor and renting a private home to stay in. The weekend was great. The apartment was located in a safe neighborhood to walk around in...
    5 of 5 stars Reviewed 11 November 2013
    From start to finish this rental was perfect. I was hesitant to rent from a private party, however great communication early on helped put me at ease. As a solo traveling female I...
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    4.5 of 5 stars (2) Very good
    Northwest Side
    2 Bedrooms / 2 Bathrooms / Sleeps 8
    travellers have booked this property
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    • Air Conditioning
    • Dishwasher
    • Hot Tub
    • Internet Access
    • Safe
    • Satellite TV
    • Washer
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    • Elder access
    • x
    About this property
    Two bedrooms, two bathrooms condo apartment on the north side of Chicago. The apartment can accommodate 4 guests comfortably, but if need be can add two inflatable mattresses to accommodate up to 8 people. FREE Wireless internet access. FREE parking on public street in front of the building.... View all property information
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    4 of 5 stars Reviewed 30 March 2015
    Condo was clean and comfortable and looked recently updated. It was in a perfect location for us. Peter and Annie were very helpful and flexible in meeting our needs. Parking is...
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    5 of 5 stars (7) Excellent
    1 Bedroom / 3 Bathrooms / Sleeps 2
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    • Air Conditioning
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    • Satellite TV
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    • Waterfront
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
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    • x
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    About this property
    Elegant 1 and 2 bedroom apartments on N Lake Shore Drive,10 min away from Michigan Avenue, Northwestern Memorial Hospital, 25 min by bus to Millenium Park and the Art Institute. Fully furnished, beautiful oak floors, high ceilings, custom architectural details.Perfect residential accommodations for... View all property information
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    5 of 5 stars Reviewed 15 April 2012
    We were in Chicago to visit our daughter and this was our first stay at this 1 bedroom apartment. It was absolutely wonderful - cozy, well-appointed and suited our needs...
    5 of 5 stars Reviewed 9 December 2011
    My friend and I were blown away by this apartment, beautifully accomodation and accessible to the city with 3 regular buses passing by. The owner was very helpful and...
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    5 of 5 stars (1) Excellent
    Northwest Side
    1 Bedroom / 1 Bathroom / Sleeps 2
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    • Air Conditioning
    • Dryer
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    • Pets allowed
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    • Suitable for children
    • x
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    • x
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    About this property
    If you are looking for a private, cozy, and comfortable place then this is just right for you. Here you can relax and lay back in a newly renovated unit with a private entrance for your convenience. Let the travel stress behind you and enjoy your stay in that great City we call HOME, Chicago We... View all property information
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    5 of 5 stars (1) Excellent
    Lakeview
    3 Bedrooms / 2 Bathrooms / Sleeps 8
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    • Pets allowed
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    • Suitable for children
    • ?
    • x
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    • x
    About this property
    CHICAGO GUEST HOUSE Tripadvisor Certificate of Excellence 2014 5.0 of 5 stars --128 Reviews on TRIPADVISOR Ranked #1 of 51 Specialty Lodging in Chicago! ************************* Beautiful & spacious--filled with charm and character! A Vintage Beauty With All the Modern Comforts & Amenities.... View all property information
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    5 of 5 stars Reviewed 26 July 2014
    What a perfect place for a family get away. The Clark Suite was perfect for our family of 7 adults. The kitchen was immaculate and well equipped with anything you needed. I...
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    5 of 5 stars (19) Excellent
    3 Bedrooms / 2 Bathrooms / Sleeps 10
    travellers have booked this property
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    • Air Conditioning
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    • Wi-Fi
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    • x
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    About this property
    Spacious Bright Loft in the Heart of Everything Chicago 2 -10 adults, up to 12 with children Our funky warehouse & former tavern turned costume factory turned fabulous Lincoln Park home can be your home away from home in Chicago. Located in Chicago's newest neighborhood - 'SONO', at the... View all property information
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    5 of 5 stars Reviewed 20 April 2015
    Traveling to Chicago for a conference with 4 colleagues and rented the Magic Factory for a few nights in early April 2015. Booking was simple and Carole & Basil were great...
    5 of 5 stars Reviewed 20 April 2015
    Beautiful, spacious loft in a convenient location. Our group of 6 stayed for the weekend. We didn't bring our cars, but it was super easy to get around because it's a very...
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    5 of 5 stars (14) Excellent
    Southwest Side
    2 Bedrooms / 1 Bathroom / Sleeps 6
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    • Air Conditioning
    • Dishwasher
    • Dryer
    • Hot Tub
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    • Elder access
    • x
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    About this property
    We have two really incredible vacation rental apartments. The view in our first picture is our large hot tub. It's your new best friend after a day of travel, sightseeing, or business. The next photo is the amazing Chicago City Skyline view from our deck (closed in winter when there is snow... View all property information
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    5 of 5 stars Reviewed 3 April 2015
    The location is in a quaint neighborhood. We enjoyed the location because you felt like part of the area. The apartment was very spacious. It was truly a home away from home...
    5 of 5 stars Reviewed 7 April 2014
    Our family of four (two teens) spent 5 days here during spring break and had an excellent experience. We went downtown every day by catching the red line train at the 35th/Sox...
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    4 of 5 stars (1) Very good
    Near North Side
    1 Bedroom / 1 Bathroom / Sleeps 2
    travellers have booked this property
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    • Air Conditioning
    • Fireplace
    • Internet Access
    • Safe
    • Satellite TV
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    Experience our 1 bedroom fully furnished “Old Town Chicago” condos designed by famous Chicago artist Edgar Miller (The Chicago Renaissance Man) with Flat Panel HDTVs, Fireplaces, All Utilities, All Major Appliances, WiFi, Internet, Cable, Queen Size Tempur-Pedic Mattresses, Cleaning Service... View all property information
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    4 of 5 stars Reviewed 20 September 2012
    We rented a one-bedroom apartment in this six-apartment building for the entire summer, so we could experience Chicago without exhausting ourselves. Cozy apartment, comfortably...
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    4 of 5 stars (5) Very good
    Rogers Park
    2 Bedrooms / 1 Bathroom / Sleeps 7
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    • Air Conditioning
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    • Pets allowed
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    • Suitable for children
    • ?
    • ?
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    • x
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    About this property
    This listing is for a private 2-bedroom apartment in the Rogers Park neighborhood of Chicago. The apartment is over 1200 square feet (111 sq meters) and has tall 9.5' ceilings (2.9 meters), a marble bath, and hardwood floors throughout. There is also a charmingly retro yet fully functional kitchen... View all property information
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    5 of 5 stars Reviewed 1 January 2015
    Lisa and Caitlin did such an amazing job making the home comfortable and I loved the books about Chicago and the Book they had made with so much helpful information! The location...
    4 of 5 stars Reviewed 2 October 2014
    Three of us stayed at at Devon property and were thrilled with the accommodations. The location to the local bus and train stops were very convenient. The hosts, Lisa and...
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    Lakeview
    2 Bedrooms / 1 Bathroom / Sleeps 4
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    • Air Conditioning
    • Dishwasher
    • Grill
    • Internet Access
    • Satellite TV
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
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    • Elder access
    • x
    About this property
    An irresistibly charming apartment! Good things do come in small packages! Walk in to the home and the first thing you notice is nothing has been taken for granted. You’ll be engulfed in warm inviting hues. The beauty & integrity of the historic homerecaptured; undeniably charming. Glance around... View all property information
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    5 of 5 stars (1) Excellent
    The Loop
    1 Bedroom / 1 Bathroom / Sleeps 2
    travellers have booked this property
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Gym
    • Hot Tub
    • Housekeeping...
    • Internet Access
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
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    • Elder access
    About this property
    Located in the chic New Eastside near Millennium Park, The Art Institute and fabulous Michigan Avenue shopping, this one-bedroom, lakefront condo is furnished with all the luxuries of a five-star hotel: Sleep Number queen bed, Nespresso coffee maker, digital television, pool, gym, rooftop views of... View all property information
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    5 of 5 stars Reviewed 29 April 2015
    I was traveling in town for business and decided to rent this condo instead of staying at a hotel. I cannot say enough positive things. The price was reasonable, the views of...
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    4 of 5 stars (1) Very good
    Near North Side
    1 Bedroom / 1 Bathroom / Sleeps 2
    travellers have booked this property
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    • Air Conditioning
    • Fireplace
    • Internet Access
    • Safe
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    Experience our 1 bedroom fully furnished “Old Town Chicago” condos designed by famous Chicago artist Edgar Miller (The Chicago Renaissance Man) with Flat Panel HDTVs, Fireplaces, All Utilities, All Major Appliances, WiFi, Internet, Cable, Queen Size Tempur-Pedic Mattresses, Cleaning Service... View all property information
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    4 of 5 stars Reviewed 29 September 2014
    The apartment was more spacious and comfty than it appeared in photos. The location was excellent, we had everything we could need at much 2 blocks away (restaurants, bars...
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    5 of 5 stars (32) Excellent
    Northwest Side
    1 Bedroom / 1 Bathroom / Sleeps 2
    travellers have booked this property
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    • Air Conditioning
    • Dryer
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • x
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    • Elder access
    • x
    About this property
    A big thank you to my guests for their great reviews. I'm so honored to have earned a 2014 Certificate of Excellence from tripadvisor! Very comfortable, private lower level of duplex. Perfect for a business traveler who doesn't want to be downtown, or a couple visiting the city for pleasure.... View all property information
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    4 of 5 stars Reviewed 10 December 2014
    Cheryl's apartment worked perfectly as a home base for my husband and me during a long weekend's visit to Chicago. We spent much of our time in and around the Loop, but found the...
    5 of 5 stars Reviewed 14 November 2014
    My husband and I rented the apartment for 5 days in early November. I was attending a Conference downtown and did not want to pay the high price hotel. This place was perfect...
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    5 of 5 stars (9) Excellent
    Northwest Side
    Studio / 1 Bathroom / Sleeps 2
    travellers have booked this property
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    • Air Conditioning
    • Dryer
    • Grill
    • Satellite TV
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
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    • Elder access
    • x
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    About this property
    The studio is situated in the couch house of the property. It is 300 square feet plus the bathroom. Beautiful decorated and very quiet place with the windows facing the beautiful garden. There is a washer and dryer on side and we can offer also breakfast. View all property information
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    5 of 5 stars Reviewed 20 September 2014
    The place is immaculate. Super clean and fully equipped. The location is great. You have the subway blue line (to downtown) in a short walk from the house to the station. The...
    5 of 5 stars Reviewed 1 September 2014
    I enjoyed my stay here and the hosts are warm, friendly and welcoming people. Hanne is just the sweetest person and I feel as if I have known her for many years. She always made...
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    2 Bedrooms / 1 Bathroom / Sleeps 5
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    • Air Conditioning
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    • Wi-Fi
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    • Elder access
    • x
    • ?
    About this property
    Thank you viewing this listing. I am offering a fully furnished two bedroom, one bathroom apartment. The apartment is located in the city's far West side. Conveniently located nearby is a Metra train station which travels to Chicago Union Station, located in the Loop (downtown). Another travel... View all property information
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    1 / 11
    5 of 5 stars (2) Excellent
    DePaul
    2 Bedrooms / 1 Bathroom / Sleeps 6
    travellers have booked this property
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    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    BEFORE YOU BOOK PLEASE NOTE THERE IS A 4 NIGHT MINIMUM FROM MAY THROUGH OCTOBER, WITH A 5 NIGHT MINIMUM FOR HOLIDAY WEEKENDS AND SPECIAL EVENT WEEKENDS. PLEASE DO NOT AUTO BOOK FOR PERIODS SHORTER THAN WHAT IS REQUIRED AS THE BOOKING MAY NOT BE HONORED. PLEASE EMAIL OR CALL WITH ANY QUESTIONS.... View all property information
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    4 of 5 stars (1) Very good
    The Loop
    2 Bedrooms / 2 Bathrooms / Sleeps 5
    travellers have booked this property
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    • Balcony
    • Dryer
    • Grill
    • Gym
    • Hot Tub
    • Internet Access
    • Private Outdoor...
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
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    • Elder access
    About this property
    The Tides is a great way to experience life and culture in the heart of Chicago! Featuring a modern contemporary feel, the short term rentals at The Tides offer dramatic finishes including tiled entries, granite islands and cherry cabinetry, open floor plans with captivating views from the... View all property information
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    4 of 5 stars Reviewed 5 February 2015
    This apartment is located in a modern, somewhat glitzy group of buildings which form their own mini-village. It is located east of Michigan Ave., almost across the street from...
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    5 of 5 stars (2) Excellent
    DePaul
    2 Bedrooms / 1 Bathroom / Sleeps 4
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    • Air Conditioning
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
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    • Elder access
    • x
    • ?
    About this property
    This Unit has one regular sized bedroom and a 'Lil' bedroom - twin bed only. Located 1 block from the Fulllerton L stop (Brown Purple & Red Line service), getting around the Windy City is a breeze. Magnificent Mile in under 10 minutes, the Loop (Grant Park, Millennium Park, Museum Row) in 12. With... View all property information
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    5 of 5 stars (36) Excellent
    3 Bedrooms / 1 Bathroom / Sleeps 6
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    • Air Conditioning
    • Balcony
    • Dryer
    • Fireplace
    • Internet Access
    • Safe
    • Satellite TV
    • Washer
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
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    • Elder access
    • x
    About this property
    City of Chicago Vacation LICENSE NO.: 2087699 This Vintage Early 1900’s 2-Flat 2nd floor apartment is in the beautiful tree-lined neighborhood of Andersonville. Located in the FUN, EXCITING, ECLECTIC ANDERSONVILLE Neighborhood on the north side of Chicago less than 2-blocks west of Clark Street... View all property information
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    5 of 5 stars Reviewed 31 March 2015
    This apartment was wonderful. It was clean and accessible to the trains. The parking was great. I was able to find street parking within 1/2 block at all times. The...
    4 of 5 stars Reviewed 29 December 2014
    Enjoyed our stay! Plenty of space and amenities. Easy street parking. Three comfy beds, well stocked kitchen, plenty of towels. Could have used a little stronger internet and...
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    1 / 19
    Studio / 3 Bathrooms / Sleeps 10
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
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    • Elder access
    • ?
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    About this property
    Spacious 4 bedroom 3 ½ bathroom penthouse duplex feels like a single family. Set upon a quiet gas-lit street, this 2,640 square foot home boasts soaring ceilings, elegant & original detail, renovated eat-in kitchen and gorgeous hardwood floors throughout. With a walking score of 89 this home is... View all property information
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    1 / 37
    4 of 5 stars (5) Very good
    Near North Side
    2 Bedrooms / 2 Bathrooms / Sleeps 5
    travellers have booked this property
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    • Air Conditioning
    • Internet Access
    • Satellite TV
    • Washer
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • Wheelchair access
    • Elder access
    • ?
    About this property
    Studio Apartment Downtown Chicago Millennium Park walking distance most attractions close to public transportation... View all property information
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    4 of 5 stars Reviewed 18 August 2014
    Very strategic location near to major attractions. Very spacious and quiet. The best coffee is just down the building! The only thing was the wifi was extremely slow, me and my...
    3 of 5 stars Reviewed 1 July 2014
    security was not aware of our check in and had to call and verify. kitchen is not adequately stocked for those who may use knives, forks and wine glasses. it was, however...
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    5 of 5 stars (4) Excellent
    DePaul
    1 Bedroom / 1 Bathroom / Sleeps 3
    travellers have booked this property
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    • Air Conditioning
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
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    • Elder access
    • ?
    About this property
    NOTE This calendar is updated weekly not daily. Please visit www.LincolnParkVacationRentals.com for the most accurate information or email inquiry@lincolnparkvacationrentals.com to inquire about this or our other units at the same location. Please also note that holiday weeks and special event... View all property information
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    5 of 5 stars Reviewed 18 July 2012
    We first stayed at this holiday rental last summer when visting our son at Depaul university. The location of the rental is good for exploring the lincoln park area and an...
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    4 of 5 stars (1) Very good
    The Loop
    Studio / 1 Bathroom / Sleeps 2
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    • Air Conditioning
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    • Pets allowed
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    • Suitable for children
    • x
    • x
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    • Elder access
    • ?
    About this property
    Studio Apartment Downtown Chicago Millennium Park walking distance most attractions close to public transportation... View all property information
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    4 of 5 stars Reviewed 20 August 2014
    Tr`es bien situé, propre et bien équipé. Personnel de l'immeuble bien chaleureux. Pitsfield's café `a ne pas manqué au rez-de-chaussée. Calme , bien insonorisé...`a l'exeption de...
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    5 of 5 stars (30) Excellent
    Southwest Side
    3 Bedrooms / 1 Bathroom / Sleeps 6
    travellers have booked this property
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    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Hot Tub
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    We have two really incredible vacation rental apartments. The view in our first picture is our large hot tub. It's your new best friend after a day of travel, sightseeing, or business. The next photo is the amazing Chicago City Skyline view from our deck (closed in winter when there is snow... View all property information
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    5 of 5 stars Reviewed 13 November 2014
    Our family of four had an excellent time at this apartment. Bob was very easy to deal with and extremely helpful. Key code access to the apartment was very convenient. A garage...
    4 of 5 stars Reviewed 27 September 2014
    We were very pleased with our stay at this facility. It isn't in the typical touristy area which we liked as it made our urban experience feel more authentic and any neighbors we...
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    1 / 6
    1 Bedroom / 1 Bathroom / Sleeps 2
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    • x
    • x
    About this property
    The Hotel Blake*, situated in downtown Chicago's urban Printer's Row district, offers a relaxing retreat and easy access to everything the city has to offer. Unwind in your spacious accommodations, complete with soaring ceilings, exquisite bathrooms and stunning city views. Each room is designed... View all property information
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    Chicago Vacation Rentals

    Planning a visit to Chicago? A Chicago vacation rental is a great hotel alternative. From modern apartments on the Magnificent Mile to cozy coach houses in Lincoln Park and everything in between, we’ve got a wide variety of Chicago vacation rentals so there’s sure to be one that’s just right for you. Whatever your budget, we’ll help you find a great deal. Plus, you can book with confidence - we have plenty of unbiased user reviews of Chicago vacation rentals!

    Chicago family vacations

    Chicago is a great city for families and a vacation home rental makes it easy to explore all that the second city has to offer. If it’s baseball season, catch a Chicago Cubs game at historic Wrigley Field, one of the oldest ball parks in the country. Or take the kids out to Navy Pier, which features amusement rides, shops and restaurants right on Lake Michigan. If you’re kids are animal lovers, visit the Great Ape House at the Lincoln Park Zoo, where admission is still free. Or see dinosaurs at The Field Museum of Natural History.

    Chicago attractions

    There's plenty to do in Chicago and a vacation rental in the city will put you within walking distance of most of the city's many attractions. Art lovers will enjoy the Art Institute of Chicago where they can browse the large collection of impressionist and post-impressionist paintings before heading to the newer Modern Wing. After, you’ll want to head over to nearby Millennium Park, which features public art and cultural events year-round. During the warmer months, find a spot on the sand at Oak Street Beach, a great place to people watch with views of downtown skyscrapers and Lake Michigan.

    Chicago day trips

    For those who want to explore Chicago beyond the city center, there are plenty of short getaways worth exploring, all within an hour or two of your vacation rental. Nearby Oak Park is home to the Frank Lloyd Wright Home and Studio. It’s also the birthplace of Ernest Hemingway. For those looking for outdoor adventure, head south to Starved Rock State Park where you can hike miles of trails through rolling hills or go fishing, boating or horseback riding. Other popular getaways include Lake Geneva in southern Wisconsin or the shores along Lake Michigan outside the city.

    Saving money on Chicago vacation rentals

    Whether you want to stay in a chic downtown apartment rental in Chicago or a spacious house in the suburbs, we can help you find a deal that fits your budget. There are discounts on every type of property to help you get the most bang for your buck.