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.

Apartment Rentals and Condos in Chicago, IL

Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
There are no pins in your viewport. Try moving the map or changing your filters.
mm/dd/yyyy mm/dd/yyyy
    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}
    List your property
    Payment Protection
    Use a credit card to book with our Payment Protection.Learn more
    Show Prices
    Change Dates
    Price
    per night
    |||
    |||
    $0
    $174 Average
    $1,000+
    Bedrooms
    Any
    Amenities
    Any
    Neighborhood
    Any
    Payment
    Book Online
    View Map
    More filters
    loading...
    Travelers to Chicago are booking May dates now. Secure your vacation rental today, and have the perfect trip.
    Northwest Side, Wicker Park / Bucktown
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
    Show Prices
    Payment Protection
    1 / 11
    4.5 of 5 stars (4) Very good
    Roscoe Village
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    Show Prices
    1 / 38
    4 of 5 stars (2) Very good
    Near North Side
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
    other travelers have booked this property
    Show Prices
    Payment Protection
    1 / 11
    2 of 5 stars (1) Poor
    Rogers Park
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
    other travelers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Patio
    • Air Conditioning
    • Wi-Fi
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    The Space Living room and dining room combo. Rooms are nice and cozy, cute and quiet. The unit is located in the East Rogers Park neighborhood of Chicago and border with Edgewater, within walking distance to the CTA Red Line Loyola station, Loyola University, restaurants, coffee shops, Lake... View all property information
    Location Information
    Chicago, Illinois 60626
    The Loop
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Shared Yard
    • Grill
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Magnificent mile 1 brm convertible apt off Michigan Avenue in hotel district featuring 24 hr doorman, rooftop gym, sundeck, business ctr and garden patio. Your neighbors are the Hyatt, Fairmont and Radisson Blue. Gym, sundeck on rooftop 48th floor. Insane winter reductions!! North side prices in... View all property information
    Location Information
    Chicago, Illinois 60601
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    other traveler has booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Internet Access
    • Parking
    • Satellite TV
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • ?
    • x
    About this property
    Serenity Home offers hardwood floors. our home includes A fully equip kitchen, very spacious living room, Family room, and a work out area. Its perfect for: working, meetings, family get-away or just a time for peace and quietness. Serenity Home is Located when driving less then 20 minutes from... View all property information
    Location Information
    Chicago, Illinois 60644
    1 / 30
    Lakeview
    6 Bedrooms, 2 Bathrooms, Sleeps 16 | Quick View
    Show Prices
    Amenities & Details
    • Balcony
    • Air Conditioning
    • Grill
    • Parking
    • Patio
    • Internet Access
    • Washer
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Chicago Vacation Rental lenience # 2320200 This well kept property sleeps up to 16 comfortably. Enjoy the nice Wrigley Located property with great outdoor space and a sunny interior. Additional bonus includes a a huge patio/ lounge with grill and garden and a two car garage. Between the... View all property information
    Location Information
    Chicago, Illinois 60613
    1 / 6
    3.5 of 5 stars (3) Average
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
    other travelers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Internet Access
    • Washer
    • Hot Tub
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Charming, roomy one bedroom , with open kitchen and living space. This recently refurbished loft-style apartment gives visitors to Chicago a chance to visit and explore whist enjoying the comforts of modern living. Hardwood floor, and ceramic tiles in kitchen and bathroom. Plenty of sitting... View all property information
    Location Information
    Chicago, Illinois 60618
    4 of 5 stars Reviewed September 16, 2014
    The accommodations were not real fancy but well suited for a busy stay in Chicago! Excellent location for the price. Wrigley and other top sites are easily accessible. If you are...
    3 of 5 stars Reviewed June 15, 2014
    Ok so if you're expecting a pretty little getaway in Chicago with views and a location then this place isn't for you. The apartment is located atop of a commercial building that's...
    See all reviews
    Lakeview
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Shared Yard
    • Internet Access
    • DVD Player
    • Terrace
    • Washer
    • Air Conditioning
    • Balcony
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Next time you explore The Windy City, live like a local by staying at this inviting Chicago vacation rental apartment! Situated on a quiet, tree-lined street in the middle of the popular Lakeview, Wrigleyville and Boystown neighborhoods, this wonderful property is just blocks away from countless... View all property information
    Location Information
    Chicago, Illinois 60657
    1 / 28
    2 of 5 stars (1) Poor
    West Town
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
    other travelers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Wi-Fi
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Popular and convenient WEST TOWN 1 Bedroom 1 Bath Garden apartment nestled right in between Wicker Park, Ukrainian Village and trendy West Loop areas, steps away from the hottest new restaurants on Randolph Street. FOODIE HEAVEN w/ Subzero fridge, new granite kitchen stainless steel double oven!... View all property information
    Location Information
    Chicago, Illinois 60642
    List your property for free!
    List your vacation rental where TripAdvisor travelers can find it.
    Add a Listing
    1 / 17
    5 of 5 stars (39) Excellent
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Patio
    • Satellite TV
    • Internet Access
    • Balcony
    • Air Conditioning
    • Parking
    • Porch
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • 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
    Location Information
    Chicago, Illinois 60640
    5 of 5 stars Reviewed August 24, 2015
    We stayed here during a family trip, and the apartment was absolutely beautiful. Even with a family of six, the apartment was more than spacious and accommodating. Every room was...
    5 of 5 stars Reviewed June 1, 2015
    Paul was a great host, responsive and clear. The location is so fantastic if you want to experience a charming Chicago neighborhood. Restaurants, bars, cafes, and shopping are...
    See all reviews
    1 / 10
    5 of 5 stars (1) Excellent
    Lakeview
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
    other travelers have booked this property
    Show Prices
    Payment Protection
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • 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
    Location Information
    Chicago, Illinois 60657
    5 of 5 stars Reviewed October 13, 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...
    See all reviews
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Satellite TV
    • Patio
    • Wi-Fi
    • Children's Pool
    • Air Conditioning
    • DVD Player
    • Housekeeping...
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    LOCATION! LOCATION! LOCATION! Amazing Luxury location - Come relax and enjoy after a great day of sightseeing, McCormick Place or working in the comfort and convenience of this cozy home. Luxurious 2 bedroom and 2 bathroom accommodates . Centrally located to every major attraction in the Chicago... View all property information
    Location Information
    Chicago, Illinois 606016
    Northwest Side
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Housekeeping...
    • Terrace
    • Grill
    • Hot Tub
    • Balcony
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Wrap up 2015 and get the New Year off to a great start by making this 1800 sq ft condo your new home! Fully furnished, all utilities included, HBO, High Speed Internet...Everything is ready to go. When considering real estate, everyone has heard that the only three factors that matter are... View all property information
    Location Information
    Chicago, Illinois 60642
    1 / 8
    Roscoe Village
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Amenities & Details
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Located in the Heart of Roscoe Village--'A village within the city.' Trendy Roscoe Village offers a variety of boutiques, restaurants and bars. We are approximately 7 blocks from the Paulina brown stop, which will take you downtown in approximately 15 minutes. We are also located a short... View all property information
    Location Information
    Chicago, Illinois 60618
    1 / 11
    4.5 of 5 stars (8) Very good
    Near North Side
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
    Show Prices
    Amenities & Details
    • DVD Player
    • Hot Tub
    • Balcony
    • Internet Access
    • Shared Outdoor Pool...
    • Satellite TV
    • Washer
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    1 bedroom fully furnished apartment in the heart of Gold Coast/River North, walking distance to transportation, restaurants and the lake front. The apartment comes fully furnished, has equipped kitchen, flat screen TVs, basic cable, Internet, phone and all utilities are included. The price also... View all property information
    Location Information
    Chicago, Illinois 60654
    3 of 5 stars Reviewed August 5, 2015
    This place was in a great location, right around the corner from Grand Station on the red line. There is a grocery store Jewel-Osco on the block and quite a few restaurants...
    5 of 5 stars Reviewed June 26, 2014
    My husband and I stayed in a 1 bedroom apartment on the 34th floor of the AMLI River North building for 3 weeks. We rented the unit through Manilow Suites, a short term corporate...
    See all reviews
    The Loop
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Balcony
    • Internet Access
    • Satellite TV
    • Washer
    • Terrace
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    Chicago Condo Rental 1 Bedroom, 1 Bathroom, Sleeps 3 Completely equipped condo, concierge services, valet parking. Walk to Chicago attractions.Best restaurants or have .meals in the condo. Have different setups reserved at different times. Elevators, modern safety features. Can't wait to get... View all property information
    Location Information
    Chicago, Illinois 60601
    Lakeview
    3 Bedrooms, 1 Bathroom, Sleeps 8 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    This renovated apartment is in an oasis while enjoying all the excitement that Wrigleyville and Chicago have to offer! Walk to Wrigley Field, CTA Red Line, nightlife, bars, restaurants and more! Lots of space in an awesome location - and a beautiful space! With three bedrooms, each with it's own... View all property information
    Location Information
    Chicago, Illinois 60613
    1 / 10
    5 of 5 stars (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Amenities & Details
    • Balcony
    • Internet Access
    • Air Conditioning
    • Terrace
    • Washer
    • Grill
    • Secure Parking
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Live like a local and save! Book now to take advantage of discounted fall rates! Beautiful 2 Bedroom unit in boutique luxury building with 24 hour concierge service. Located in the wonderful and historic Andersonville neighborhood, The Guesthouse Chicago vacation rental encourages you to live... View all property information
    Location Information
    Chicago, Illinois 60640
    5 of 5 stars Reviewed May 18, 2015
    Great property in Chicago, a short distance from Lakeshore Drive, perfect for a family vacation. We stayed in the spacious 2 bed/2 bath unit. The unit was stunning, with beautiful...
    See all reviews
    Near North Side
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    • Shared Outdoor Pool...
    • Internet Access
    • Grill
    • Satellite TV
    • Patio
    • Washer
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    Newly (2015) furnished 2BR/1B. Queen in master BR, day bed in BR 2 and convertible love seat in the LR. Hardwood floors, granite kitchen counter top, marble bathroom. Custom cellular shades open from top and bottom to control light and setting sun. 24 hour doormen, and package receipt service.... View all property information
    Location Information
    Chicago, Illinois 60611
    Get the List
    Near North Side
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
    other travelers have booked this property
    Show Prices
    Payment Protection
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    ENTIRE SPACE This is an ideal location for visitors. This is modest but nice and completely private studio condo in the Gold Coast located near Water Tower Place, the Hancock Tower, and the Museum of Contemporary Art. It’s 1/2 block from the public transportation stop ( trains and buses), 4 blocks... View all property information
    Location Information
    Chicago, Illinois 60610
    1 / 23
    5 of 5 stars (1) Excellent
    DePaul
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    other traveler has booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Grill
    • Patio
    • Wi-Fi
    • DVD Player
    • Balcony
    • Washer
    • Parking
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Historic cottage in exclusive Lincoln Park neighborhood. 3 bedrooms (1 King and 2 Queens); 2 full and 1 half bath; laundry; full kitchen and family room; media room; 2 car garage; living and dining room; outdoor decks; walking distance to DePaul University, Lincoln Avenue entertainment district,... View all property information
    Location Information
    Chicago, Illinois 60604
    5 of 5 stars Reviewed September 2, 2015
    My friends and I spent the weekend at Paul's house for our fantasy football draft. The house is in walking distance to Wrigley field and lake shore drive. It easily accommodates 6...
    See all reviews
    1 / 11
    1 of 5 stars (1) Terrible
    2 Bedrooms, Sleeps 6 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Internet Access
    • Washer
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Stay in the heart of Chicago A fitness centre and apartments with a full kitchen are featured at the Ginosi Chicago Suites. The Chicago property is 350 metres from 360 Chicago and 300 metres from Loyola University Museum of Art. Free WiFi access is provided. The apartment will provide you with a... View all property information
    Location Information
    Chicago, Illinois 60611
    1 / 9
    5 of 5 stars (1) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    other travelers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Parking
    • Satellite TV
    • Air Conditioning
    • DVD Player
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Come one Come all Enjoy yourself at my beautiful 2 level condo. This modern beauty features granite, 2 full bathrooms, jet tub, 3 bedrooms, 2 sitting rooms. Enjoy cable tv in every room. The modern decor is absolutely gorgeous. If you need to bring the family, or if you are in town for business,... View all property information
    Location Information
    Chicago, Illinois 60620
    5 of 5 stars Reviewed October 21, 2015
    We were a bit worried about renting in the Southside due to things we had heard. We loved the condo and the neighbor's were friendly and welcoming. We never felt threatened or in...
    See all reviews
    1 / 4
    Roscoe Village
    4 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
    Show Prices
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Brand new 4 bedroom 2 bath fully furnished apartment in Roscoe Village close to Hamlin Park. Whether you are planning a weekend excursion, business trip or need a comfortable place to stay for family or friends, consider our newly rehabbed Guesthouse on Leavitt St. We do allow 1-2 nights stays... View all property information
    Location Information
    Chicago, Illinois 60618
    1 / 11
    Near North Side
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
    Show Prices
    Amenities & Details
    • Internet Access
    • Satellite TV
    • Private Outdoor...
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    This all-suite hotel is located in downtown Chicago, surrounded by upscale dining and shopping in the trendy River North neighborhood. It features a breakfast buffet and free Wi-Fi throughout the property. Two flat-screen TVs are included in each suite. The kitchenette has a 2-burner stove and... View all property information
    Location Information
    Chicago, Illinois 60611
    1 / 17
    Roscoe Village
    2 Bedrooms, 1 Bathroom, Sleeps 8 | Quick View
    Show Prices
    Amenities & Details
    • Parking
    • Satellite TV
    • Washer
    • Grill
    • Internet Access
    • Air Conditioning
    • Patio
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Beautifully rehabbed with brand new eat-in kitchen and bath. Hardwood floors throughout apartment. All trim and woodwork has been magnificently restored to it's original look. Washer and dryer in unit Central air with individual controls for heat and AC. Guest love the huge outdoor finished space... View all property information
    Location Information
    Chicago, Illinois 60618
    1 / 7
    5 of 5 stars (1) Excellent
    Near North Side
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Amenities & Details
    • Internet Access
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Top floor unit in historic Old Town Neighborhood. Close to shopping, Brown Line El stop. Downtown . And North Avenue Beach! We do allow 1-2 nights stays Monday-Thursday with a cleaning fee. Over any weekend we have minimum nights stay of 3,4,5 or 6 nights. Please ask how many nights your... View all property information
    Location Information
    Chicago, Illinois 60614
    5 of 5 stars Reviewed October 4, 2012
    The apartment is 2 bed, 2 bath, apartment was spotless upon arrival. Bathrooms were spotless, fresh bed linen and fresh towels. Great location, well worth staying here as only 5...
    See all reviews
    Hyde Park
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
    other travelers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Our brand new master suite's high ceilings, Juliet balcony and modern, yet rustic finishes, will leave you feeling refreshed. Just steps away from the U of C,, our place fits two and is perfect for future students and families looking to be nearby! This private bedroom and bath are located on the... View all property information
    Location Information
    Chicago, Illinois 606155114
    The Loop
    2 Bedrooms, 4 Bathrooms, Sleeps 5 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Balcony
    • Terrace
    • Shared Yard
    • Grill
    • Wi-Fi
    • Shared Indoor Pool
    • Washer
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Fabulous 2 bedroom apartment. 3 queen beds, sofa, 2 bathrooms. Great views and amazing amenities. Very close to Michigan & State. Within walking distance to the Lake and Millennium Park. All subway lines just few steps away. Apt has wifi, cable. Clean and modern high rise, two bedroom apartment,... View all property information
    Location Information
    Chicago, Illinois 60601
    1 / 16
    5 of 5 stars (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
    other traveler has booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Grill
    • Patio
    • DVD Player
    • Balcony
    • Air Conditioning
    • Wi-Fi
    • Housekeeping...
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    LOCATION,LOCATION, LOCATION!!!! Newly listed amazing home in great location - Luxurious 2 bedroom, 3 bed, 2 bath condo with amazing views in multiple directions, centrally location to every major attraction in the Chicago-land area and easy access to all city transit. There are three bedrooms in... View all property information
    Location Information
    Chicago, Illinois 60605
    5 of 5 stars Reviewed September 16, 2015
    I emailed D (the owner) multiple times and she was so sincere and helpful with our requests... she really went out of her way for our family. She spent over 25 minutes on the...
    See all reviews
    The Loop
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Patio
    • Air Conditioning
    • Washer
    • Sauna
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Where the classics never go out of style! Formally the Steuben Building, this Historic Landmark is now an environmentally friendly green building. Located in the Chicago Loop within walking distance of the Theater District, Magnificent Mile, River North, and Gold Coast restaurants and bars,... View all property information
    Location Information
    Chicago, Illinois 60601
    1 / 37
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    Show Prices
    Amenities & Details
    • Grill
    • Internet Access
    • Parking
    • Balcony
    • Air Conditioning
    • DVD Player
    • Washer
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Large Rental In A Neighborhood That Has Kept Its Old World Charm With The New! Large, Cozy Place Ideal For Value Seekers Looking For A Memorable And Culturally-diverse Experience In A Quaint Neighborhood That's Also A Convenient Base To Explore Other Fun Sites In Chicago. From A Relatively... View all property information
    Location Information
    Chicago, Illinois 60625
    1 / 11
    4.5 of 5 stars (3) Very good
    Roscoe Village
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Amenities & Details
    • Air Conditioning
    • Internet Access
    • Outdoor Dining Area
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Trendy Roscoe Village offers a variety of boutiques, restaurants and bars. Our Guesthouse is located above Cinnamon Boutique, a new women's clothing and accessory store and one of many fantastic places to shop in the village. We are approximately 4.5 blocks from the Paulina brown stop, which will... View all property information
    Location Information
    Chicago, Illinois 60618
    3 of 5 stars Reviewed September 23, 2014
    I normally don't do reviews, but let me first start by saying that you would be hard pressed to find a more spacious and beautiful apartment in Roscoe Village. The location is...
    5 of 5 stars Reviewed July 20, 2013
    We spent the long July 4th weekend visiting Chicago, and stayed in #3. The space worked very well for two couples. Rather than stay in a downtown hotel, we opted for a place with...
    See all reviews
    1 / 29
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
    Show Prices
    Amenities & Details
    • Washer
    • Shared Outdoor Pool...
    • Hot Tub
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    About this property
    This beautiful unit features Eastern views of the Chicago skyline, including Willis (Sears) Tower. White quartz countertops, two-tone cabinetry, Frigidaire stainless steel appliances, gas stoves and white glass mosaic tile backsplash Full size washer/dryer Custom designed wide plank flooring... View all property information
    Location Information
    Chicago, Illinois 60607
    Northwest Side
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
    other travelers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Wi-Fi
    • Satellite TV
    • Grill
    • Parking
    • Patio
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • 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
    Location Information
    Chicago, Illinois 60707
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    About this property
    Andersonville, Edgewater, Loyola's campus and great restaurants, like Uncommon Ground, are a block away. Shopping and the lakefront are less than a 5 min walk away. There's no need for a car here, it's a short walk to the red line. The Space This is a large, bright, happy space. The apartment is... View all property information
    Location Information
    Chicago, Illinois 60660
    West Town
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    • Washer
    • Grill
    • Patio
    • Parking
    • Internet Access
    • Air Conditioning
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • Smoking allowed
    • Elder access
    • x
    About this property
    Spacious 1Bd/1Ba loft in trendy West Loop. Next to all the best restaurants and bars Chicago has to over - The Girl and the Goat, Bar Sienna, Aviary, Au Cheval to name a few. Whole foods 4 blocks away. Amenities Include Doorman Building Parking (Included) Gourmet Kitchen Nespresso Coffee Maker... View all property information
    Location Information
    Chicago, Illinois 60607
    The Loop
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    • Satellite TV
    • Washer
    • Air Conditioning
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    A kitchenette is provided in every spacious suite at Grand Riverfront at Chicago. Extras include a sofa bed and flat-screen cable TV. Private bathrooms also come with a bath or shower. A fitness centre is available at Grand Riverfront at Chicago. Other facilities like meeting facilities, luggage... View all property information
    Location Information
    Chicago, Illinois 60601
    DePaul
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Balcony
    • Grill
    • Terrace
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    This unique 2BR property located in the heart of Lincoln Park and was designed by a famous Chicago architect who prided himself in creating unique residential spaces using a multitude of elevations and classic straight line experiences. Location * 3! This apartment is a gift. You are literally a... View all property information
    Location Information
    Chicago, Illinois 60614
    1 / 24
    4.5 of 5 stars (7) Very good
    The Loop
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Amenities & Details
    • DVD Player
    • Waterfront
    • Internet Access
    • Air Conditioning
    • Satellite TV
    • Parking
    • Washer
    • Patio
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Beautiful B & B Boatel Yacht - Pier Gold offers Chicago visitors a great alternative to regular hotel stays. Located at Chicago's most sought after harbor in the heart of our city waterfront; at Burnham Harbor you will enjoy waking up at your floating waterfront boatel at our harbor with stunning... View all property information
    Location Information
    Chicago, Illinois 60605
    4 of 5 stars Reviewed July 31, 2014
    This was absolutely a great choice for a buddy and I to hang out in Chicago for a long weekend. The location was incredible and fortunately for so was the weather. Having done...
    5 of 5 stars Reviewed August 8, 2013
    A short walk (about a block) from the museums you find yourself in the quiet Burnham Harbor and on you very own Yacht! Two very private cabins, a comfortable living area with...
    See all reviews
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Terrace
    • Wi-Fi
    • Parking
    • Air Conditioning
    • Grill
    • Balcony
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Live like a local in one of Chicago's best neighborhoods at a top-rated TripAdvisor property! Located in the vibrant and historic Andersonville, our spacious apartments are ideal for guests looking for a special getaway. Unit includes gourmet kitchen with breakfast bar, king size bed, and balcony... View all property information
    Location Information
    Chicago, Illinois 60640
    1 / 7
    5 of 5 stars (1) Excellent
    Northwest Side
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
    other travelers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Shared Yard
    • Air Conditioning
    • Internet Access
    • DVD Player
    • Satellite TV
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    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
    Location Information
    Chicago, Illinois 60618
    5 of 5 stars Reviewed October 24, 2013
    This is a great place to stay, especially if you are traveling on a budget. It is about half the price you will pay for a hotel, and you get a kitchen, living room, bedroom, etc...
    See all reviews
    1 / 8
    Northwest Side
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
    Show Prices
    Amenities & Details
    • Internet Access
    • Air Conditioning
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Vintage Mansion on Kedzie Blvd - Vacation Rental License xxxxxx property. This apartment is located on the 3rd floor of a Historic Mansion, overlooking Kedzie Blvd. in the city of Chicago. The apartment is very spacious, approximately 1200 sq ft of space, large living room, dinning and... View all property information
    Location Information
    Chicago, Illinois 60647
    Southwest Side
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Patio
    • Washer
    • Hot Tub
    • Satellite TV
    • Internet Access
    • Parking
    • DVD Player
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Lounge in comfort and luxury for a reasonable price only 10 mins away the heart of downtown Chicago. The spacious apartment features 2 separate living rooms, gourmet kitchen, private bedroom and bathroom, kitchen and laundry room. The kitchen and laundry room are the only shared spaces in the... View all property information
    Location Information
    Chicago, Illinois 60609
    1 / 21
    5 of 5 stars (1) Excellent
    Near North Side
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
    other travelers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Satellite TV
    • Wi-Fi
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    Whether you are coming to stay at Raffaello Chicago for business, a romantic getaway, or traveling with your family and friends, we have the perfect accommodation ready and waiting for you. Every Raffaello guest room reflects an upscale European style with soothing accents, subtle earth tones and... View all property information
    Location Information
    Chicago, Illinois 60611
    5 of 5 stars Reviewed February 27, 2015
    We were lucky that we chose this place. It is in a perfectly managed hotel , Raffaello Hotel . Everything was ready to have a nice stay. Thanks
    See all reviews
    Rogers Park
    4 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
    other traveler has booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    6900 North Sheridan boasts custom italian cabinetry, high-end appliances, wall-to-wall porcelain tile, heated bathroom floors, spacious living and dining areas. The unit is over 2100 sq.ft of space which is perfect for corporate housing or families. The unit comes fully furnished with laundry and... View all property information
    Location Information
    Chicago, Illinois 60626
    DePaul
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
    other travelers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Satellite TV
    • DVD Player
    • Internet Access
    • Grill
    • Balcony
    • Patio
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    HISTORY: Aster House has been renting since 1891, and under the present owners since 1982. We've had guests return as long as 18 years, so you may be assured of a safe secure visit. NEIGHBORHOOD: Aster House is on a quiet residential street in Lincoln Park, Chicago's most upscale downtown... View all property information
    Location Information
    Chicago, Illinois 60614
    1 / 22
    5 of 5 stars (1) Excellent
    Near North Side
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
    other travelers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Washer
    • Air Conditioning
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    The Duplex Condo is located in the vibrant Gold Coast neighborhood, one of Chicago's most affluent and treasured residential areas with quiet, tree-lined streets, stately homes and connections to the city's past. This property is in a Charming historic lowrise brick building. It has a bright and... View all property information
    Location Information
    Chicago, Illinois 60610
    5 of 5 stars Reviewed September 30, 2015
    The place was neat, confortable and very well located. We enjoyed our time, and would definitely stay there again. Vee was truly thoughtful. Absolutely recommendable
    See all reviews
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    other travelers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Satellite TV
    • DVD Player
    • Wi-Fi
    • Terrace
    • Washer
    • Grill
    • Balcony
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    3 bedrooms, 2 full bathrooms, Balcony with Grill, sleeps 8. Kid Friendly Live like a local in one of Chicago's best neighborhoods at a top-rated TripAdvisor property! Located in a family-owned boutique building in the vibrant and historic Andersonville neighborhood, our Chicago vacation property... View all property information
    Location Information
    Chicago, Illinois 60640
    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.