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Chicago Vacation Rentals

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    All 23 Rentals in Chicago
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    The following rentals are within 25 kilometres of Chicago.
    Oak Park Bungalow1 / 20
    (3)Very good
    Oak Park
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Oak Park Beauty Sleeps 1 to 8 Guests1 / 14
    (1)Excellent
    Oak Park
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Beautifully Remodeled 3 BR Townhouse near Chicago1 / 30
    (2)Excellent
    Wilmette
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Lincolnwood
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    At this Sonder, you'll love the beautiful fireplace, spacious balcony, and a fully-equipped kitchen. Located in Lakeview, know for its delicious dining and relaxed cafes. Every booking is instantly confirmed. Every call or message is answered within minutes. Every home is equipped with crisp...
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    Lincolnwood, Illinois 60613
    Condo/Apartment - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Handsome 3BR in Lake View by Sonder1 / 18
    (1)Excellent
    Lincolnwood
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 11, 2018
    Great space in a great location. Within walking distance to a number of restaurants/bars. The apartment was clean and looked just like the photos. Reservations were extremely...
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    About this property
    At this Sonder, you'll love the stunning architectural details, luxurious hardwood floors, and a spacious balcony. Located in Lakeview, known for its amazing eateries and relaxed cafes. Every booking is instantly confirmed. Every call or message is answered within minutes. Every home is equipped...
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    Lincolnwood, Illinois 60613
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Charming apartment, fantastic location! Spacious 4 bedroom, a rare find!1 / 13
    (1)Excellent
    Forest Park
    4 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Wi-Fi
    • Housekeeping Included
    • Parking
    • DVD Player
    • Grill
    • Balcony
    • Patio
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 18, 2018
    This truly is a rare find and well worth your time if you need a place with multiple bedrooms in a convenient, residential location. The owners were very responsive to messages...
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    About this property
    Charming private apartment in the heart of Forest Park! Perfect mix of cozy, chic, & antique! Long term or a quick weekend away! Ideal for couples, solo adventurers, business travelers, families, big groups, even pets! Four bedrooms, spacious living area, beautiful backyard garden with seating for...
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    Forest Park, Illinois 60130
    Condo/Apartment - 4 Bedrooms, 1 Bathroom, Sleeps 5
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    Lincolnwood
    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    • Air Conditioning
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    Pet friendly
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    Smoking allowed
    About this property
    At this Sonder, you'll love the expansive living area, sleek hardwood floors, and fully-equipped kitchen. Located in Roscoe Village, known for its hip boutiques and assortment of delicious restaurants. When you stay at a Sonder, you have a 24/7 concierge and receive all the local color of a...
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    Lincolnwood, Illinois 60618
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 7
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    River Grove
    1 Bedroom, 2 Bathrooms, Sleeps 2 Quick View
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    • Air Conditioning
    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The house is an en-suite with 7 rooms, namely; living room, dining room, 2 bedrooms/lounge area, kitchen, two baths/toilets, nice decks and more, if you need room, this is the ideal spot for you and your guests. A few blocks from the Metra Station as well as buses to take you directly to the...
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    River Grove, Illinois 60171
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 2
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    Condo
    Oak Park
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Cable/satellite TV
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    Pet friendly
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    Smoking allowed
    About this property
    When traveling and looking for an upscale location. Oak Park offer a great traveler great food, entertainment, relaxing environment. Safe and a wide array of guided tours, Frank Lloyd Widget homes is just the start. My condo has two room with king bed half bath master bedroom, 2 bedroom has queen...
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    Oak Park, Illinois 60302
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Forest Park
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Spacious 1 bedroom suite with a big screen TV, a super comfy bed & the convenience of cooking your own meals (oven, frig & microwave in your kitchen). Located on a wonderfully quiet residential block, very close to public trans and expressway. Downtown Chicago & O'Hare airport are one train ride...
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    Location Information
    Forest Park, Illinois 60130
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Melrose Park
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Central Heating
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Long modern open concept. New Renovation. Entire flat. Completely remodeled 3 bedroom 1.5 bath. Centrally located 15 min from O'hare Airport, and 20 min from Downtown at non traffic hours with easy access to the highways. This entire Melrose Park apartment flat near the 25th Ave & Lake St. features...
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    Location Information
    Melrose Park, Illinois 60160
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Lincolnwood
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Waterfront
    • Wi-Fi
    • Balcony
    • Patio
    • Terrace
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Adeline's Sea Moose hosts over night stays for yacht enthusiasts! This 68 ft luxury charter yacht is one of the few sizable multi-level private Charter yachts in Chicago, and that was built and has maintained a true private yacht. Great care has been taken to uphold the integrity of her styling....
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    Location Information
    Lincolnwood, Illinois 60712
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Oak Park
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Air Conditioning
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    Pet friendly
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    Smoking allowed
    About this property
    Beautiful Oak Park, IL home of Earnest Hemingway and Frank Lloyd Wright. We boast beautiful homes, superb restaurants, shops and we are next door to Chicago a world class city!! Welcome to my home where you will find comfortable beds, refreshments, conversation and a warm feeling of being...
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    Location Information
    Oak Park, Illinois 60302
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Summit
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • DVD Player
    • Air Conditioning
    • Cable/satellite TV
    • Grill
    • Washer
    • Hot Tub
    • Patio
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Map in the ad is wrong and Trip Advisor can't fix it. We are located in the Bridgeport neighborhood just south of downtown Chicago and just West of Guaranteed Rate Field, home of the Chicago White Sox. We are located 5 miles due south from our city center, and 3 miles from our convention...
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    Location Information
    Summit, Illinois 60501
    Condo/Apartment - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    Evanston
    2 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Parking
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    • Cable/satellite TV
    • Wi-Fi
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Hull Chateau is a delightful, bright, relaxed place. Hull Chateau is quiet and private. Guests will feel like home. The entire house is open to guests. We Provide the guests the experience of a 'Home away from home'. Hull Chateau is in a great Evanston neighborhood. Quiet, peaceful, and...
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    Location Information
    Evanston, Illinois 60202
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 7
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    Oak Park
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Cable/satellite TV
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    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    - Safe and quiet residential area by the Oak Park Arts District - Many art shops, two cafes, Italian restaurant and family-friendly activities all within walking distance. - Space is master bedroom on the 2nd floor - Free parking on premise - 15-20 mins Chicago Loop/Downtown by car - 2 mins walk to...
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    Location Information
    Oak Park, Illinois 60304
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Melrose Park
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Wi-Fi
    • Secure Parking
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This home is perfect if you want to be close to the airports and still have access to go downtown as well. You will love staying in this fully furnished and equipped home that will give you the experience as if you were staying at a place out of a modern home magazine. The TV is a smart TV with...
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    Location Information
    Melrose Park, Illinois 60160
    Condo/Apartment - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    Evanston
    1 Bedroom, 2 Bathrooms, Sleeps 3 Quick View
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    • Private Garden
    • Internet Access
    • Air Conditioning
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Pinewoods Retreat is home to a small artist community including musicians, painters and acrobats. Here you will find an eclectic yet quiet escape from the fast paced city. We take great pride in the peaceful environment that we have created here and welcome you to share in our retreat. Please...
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    Location Information
    Evanston, Illinois 60203
    Private Room - 1 Bedroom, 2 Bathrooms, Sleeps 3
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    Lincolnwood
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Parking
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    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Built in 1919, this elegant 4BR/3.5BA has been beautifully updated and features gleaming hardwood floors, stylish furniture, and tasteful art. Spread out in 3,300 square feet of comfortable living space, including two living rooms and a fenced backyard. A fantastic location in Albany Park puts you...
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    Location Information
    Lincolnwood, Illinois 60625
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Norridge
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is a clean, quiet and cozy garden apartment in an amazing area that is perfect whether you are venturing locally or traveling...
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    Norridge, Illinois 60634
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Lincolnwood
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    • DVD Player
    • Balcony
    • Terrace
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Excitement bustles around Chicago as you approach this 2-bedroom, 2.5-bathroom vacation rental townhome! With room to host 4 on beds and other sleeping arrangements, this 3-story home offers 2 living areas, a gourmet kitchen, 2-car garage, and sophisticated decor, creating a luxury accommodation in...
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    Location Information
    Lincolnwood, Illinois 60660
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 4
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    Norridge
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Air Conditioning
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    Pet friendly
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    About this property
    This is a clean, quiet and cozy apartment in an amazing area that is perfect whether you are venturing locally or traveling downtown. Located off Irving and Cumberland you are within walking distance of multiple amazing bars and restaurants and a short drive from some of the best restaurants in the...
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    Norridge, Illinois 60706
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Lincolnwood
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    This incredibly lavish 2BR apartment boasts an array of antique furniture and fixtures. Rich wall paneling, sculptures, and fine furnishings make this Andersonville getaway truly unique. Step back in time while enjoying the modern convenience of a full contemporary kitchen. Wrigleyville is a...
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    Location Information
    Lincolnwood, Illinois 60640
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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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.

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