We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Chicago Vacation Rentals

Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
Check In Check Out
    There are no pins in your viewport. Try moving the map or changing your filters.
    • {providername} {price}
    {providername} {price}
      {listitems}
    {sold_out_text}
    We can't find prices for this accommodation
    From {rate_price} {rate_periodicity}
    View Map
    Location
    Any Distance
    from
    Price
    per night
    C$223 Average
    |||
    |||
    C$0C$1,000+
    Suitability
    More filters
    Don't let other travellers get your favourite Chicago area vacation rental. You're so close to securing your perfect getaway. Book today.
    All 20 Rentals in Chicago
    Sort by:
    Default
    The following rentals are within 15 kilometres of Chicago.
    Oak Park Bungalow1 / 20
    (3)Very good
    Oak Park
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Oak Park Beauty Sleeps 1 to 8 Guests1 / 14
    (1)Excellent
    Oak Park
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Lincolnwood
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Handsome 3BR in Lake View by Sonder1 / 18
    (1)Excellent
    Lincolnwood
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/satellite TV
    • Washer
    • Air Conditioning
    • Wi-Fi
    Suitability
    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...
    See all reviews
    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...
    View all property information
    Location Information
    Lincolnwood, Illinois 60613
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Enquiry
    Lincolnwood
    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Wi-Fi
    • Washer
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    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...
    View all property information
    Location Information
    Lincolnwood, Illinois 60618
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 7
    Make Enquiry
    Charming apartment, fantastic location! Spacious 4 bedroom, a rare find!1 / 13
    (1)Excellent
    Forest Park
    4 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Housekeeping Included
    • Balcony
    • Cable/satellite TV
    • Patio
    • Grill
    • DVD Player
    • Air Conditioning
    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...
    See all reviews
    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...
    View all property information
    Location Information
    Forest Park, Illinois 60130
    Condo/Apartment - 4 Bedrooms, 1 Bathroom, Sleeps 5
    Make Enquiry
    Lincolnwood
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • 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....
    View all property information
    Location Information
    Lincolnwood, Illinois 60712
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Make Enquiry
    Condo
    Oak Park
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/satellite TV
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    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...
    View all property information
    Location Information
    Oak Park, Illinois 60302
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Make Enquiry
    Oak Park
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/satellite TV
    • Wi-Fi
    • Parking
    • Air Conditioning
    • 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...
    View all property information
    Location Information
    Oak Park, Illinois 60304
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    Make Enquiry
    Forest Park
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    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...
    View all property information
    Location Information
    Forest Park, Illinois 60130
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    Make Enquiry
    Save time - get the best Chicago rentals sent straight to your email!
    Get the List
    Oak Park
    2 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Balcony
    • Terrace
    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Perfect location in one of Chicago's trendiest neighborhoods, Logan Square! Beautiful 2 bedroom, 1 bathroom unit on the 1st floor of a Chicago walk-up with high end amenities located in the Logan Square. Perfect location for a weekend getaway, business trip (12 minute to Logan Square CTA Blue Line...
    View all property information
    Location Information
    Oak Park, Illinois 60647
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 7
    Make Enquiry
    Oak Park
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    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...
    View all property information
    Location Information
    Oak Park, Illinois 60302
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 3
    Make Enquiry
    Lincolnwood
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Air Conditioning
    • Wi-Fi
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Perfect location in Chicago's famous Wrigleyville! Beautiful 3 bedroom, 3 bath on the 1st floor (duplex down) of a Chicago walk-up with high end amenities located in the heart of Wrigleyville. Perfect location for a weekend getaway, business trip, Chicago Cubs game. Fast Wi-Fi included. 1,100+ sq....
    View all property information
    Location Information
    Lincolnwood, Illinois 60613
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Make Enquiry
    Elmwood Park
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Secure Parking
    • Washer
    • Cable/satellite TV
    • Air Conditioning
    • Wi-Fi
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Prime location. 15 minutes from O’Hara airport and 1 block away fro metro train that will take you downtown or suburbs in less then 20 minutes. Upsacale safe friendly cozy neighborhood. 5 shopping malls within 10 minutes. Parks and recreation center with free pool and gym 3 blocks away. More than...
    View all property information
    Location Information
    Elmwood Park, Illinois 60707
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 5
    Make Enquiry
    Forest Park
    5 Bedrooms, 3 Bathrooms, Sleeps 14 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Cable/satellite TV
    • Washer
    • DVD Player
    • Air Conditioning
    • Wi-Fi
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This 5BR/3BA downtown Forest Park home is walking distance to Madison Avenue's restaurants and nightlife and 6 minutes from the Frank Lloyd Wright Historic District. Beautiful artwork and fine furnishings fill the open-concept layout, and a newly renovated kitchen is sure to impress. The train...
    View all property information
    Location Information
    Forest Park, Illinois 60130
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 14
    Make Enquiry
    Oak Park
    3 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Cable/satellite TV
    • Secure Parking
    • Wi-Fi
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This beautifully decorated three bedroom apartment comes with private entry, secured free parking, cable, internet, security & stainless steel appliances. Located on a quiet tree-lined street, with well manicured landscaping we are 5 minutes from the I290 Expressway, 15 minutes from downtown...
    View all property information
    Location Information
    Oak Park, Illinois 60644
    Condo/Apartment - 3 Bedrooms, 1 Bathroom, Sleeps 5
    Make Enquiry
    Lincolnwood
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    • Balcony
    • Terrace
    • Air Conditioning
    • Cable/satellite TV
    • Wi-Fi
    • Washer
    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...
    View all property information
    Location Information
    Lincolnwood, Illinois 60660
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 4
    Make Enquiry
    Cicero
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Hello our home located 15 minutes drive to downtown Chicago , the place is brand new with all new beds sheets towels the room you will be renting out is have key that you can use to lock your stuff in the room , kitchen living room and bathroom shared with other guest if there is any during your...
    View all property information
    Location Information
    Cicero, Illinois 60623
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
    Make Enquiry
    Cicero
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Hello our home located 15 minutes drive to downtown Chicago , the place is brand new with all new beds sheets towels the room you will be renting out is have key that you can use to lock your stuff in the room , kitchen living room and bathroom shared with other guest if there is any during your...
    View all property information
    Location Information
    Cicero, Illinois 60623
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
    Make Enquiry
    Lincolnwood
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Parking
    • Wi-Fi
    • Air Conditioning
    • Grill
    • Cable/satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    THE TURNKEY ADVANTAGE Our property is TurnKey Rental Certified. All photos, amenities, calendar, and rates are 100% accurate. We will notify you proactively when early check-in / late check-outs are possible and you'll receive the comforts of home with a starter supply of shampoo, soaps, paper...
    View all property information
    Location Information
    Lincolnwood, Illinois 60618
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Make Enquiry
    List your property for free!
    List your holiday rental where TripAdvisor travellers can find it.
    Add a Listing
    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.

    List your property
    Owner log in