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Apartment Rentals and Condos in Chicago, IL

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    Travelers to Chicago are booking May dates now. Secure your vacation rental today, and have the perfect trip.
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    5 of 5 stars (2) Excellent
    The Loop
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    3.5 of 5 stars (4) Average
    3 Bedrooms, 1 Bathroom, Sleeps 8 | Quick View
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    4 of 5 stars (2) Very good
    3 Bedrooms, 1 Bathroom, Sleeps 9 | Quick View
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    About this property
    Welcome! Welcome!Our single family brick house is located in a rare semi-private block about 5 miles West of Downtown Chicago. It has 3 Bedrooms, 1 Bathroom, Living Room, Dining Room and Full Kitchen, Washer/Dryer. If you enjoy a quiet home with free parking, newer beds, clean sheets and towels,... View all property information
    Location Information
    Chicago, Illinois 60644
    5 of 5 stars Reviewed July 18, 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 May 7, 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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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Our suite features Two Bedrooms/Two Bathrooms with a pull out couch and can accommodate six guests. Suite also contains fully equipped gourmet kitchen and is perfect for families or individuals, traveling for business or pleasure. The Guesthouse Hotel offers great style, comfort and value. Stay... View all property information
    Location Information
    Chicago, Illinois 60640
    1 / 24
    5 of 5 stars (1) Excellent
    Lakeview
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    An irresistibly charming apartment! Good things do come in small packages! CHICAGO GUEST HOUSE Tripadvisor Certificate of Excellence 2015 5.0 of 5 stars --160 Reviews on Tripadvisor Ranked #1 of 55 Specialty Lodging in Chicago! Walk in to the home and the first thing you notice is nothing,... View all property information
    Location Information
    Chicago, Illinois 60657
    5 of 5 stars Reviewed June 15, 2015
    We were very happy finding this vacation rental. The location was accommodating to our interest. The apartment was excellent. We were able to stay altogether and enjoy the...
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    1 / 19
    5 of 5 stars (1) Excellent
    Lakeview
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    CHICAGO GUEST HOUSE Tripadvisor Certificate of Excellence 2015 5.0 of 5 stars --187 Reviews Beautifully furnished and fully equipped--guaranteed a unique and unforgettable experience for you, your family and friends. AMAZING LOCATION! Approximately 4 Miles North of the Heart of Downtown right... View all property information
    Location Information
    Chicago, Illinois 60613
    5 of 5 stars Reviewed April 28, 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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    1 / 17
    The Loop
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    About this property
    Please call/e-mail for more information. Beds: 2 Queen Beds View all property information
    Location Information
    Chicago, Illinois 60602
    1 / 8
    Northwest Side
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    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
    1 / 6
    Roscoe Village
    4 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    About this property
    Brand new 4 bedroom 2 bath fully furnished apartment in the heart of Roscoe Village. Whether you're planning a weekend excursion, business trip or need a comfortable place to stay for family or friends, consider our newly rehabbed Guesthouse on Roscoe St. Trendy Roscoe Village offers boutique... View all property information
    Location Information
    Chicago, Illinois 60657
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    1 / 23
    5 of 5 stars (1) Excellent
    DePaul
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    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...
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    1 / 30
    5 of 5 stars (1) Excellent
    Lakeview
    4 Bedrooms, 4 Bathrooms, Sleeps 14 | Quick View
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    $295
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    About this property
    License#2314739 This is a luxury property consistent of two units one above the other. Book one or both to accommodate the size of your group. A total of 4 bedroom 4 bath brand new construction luxury condos. We are a licensed vacation rental property with the City of Chicago... View all property information
    Location Information
    Chicago, Illinois 60613
    5 of 5 stars Reviewed May 26, 2015
    This rental was absolutely amazing. The owners were very easy to get a hold of & the place was very clean, updated, and accommodated our group of 13 perfectly. The location was...
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    1 / 16
    5 of 5 stars (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    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...
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    1 / 14
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    $315
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    About this property
    **W**O**W** Actually in Times Square. Minutes to everything in NYC. - Times Square - Rockefeller Center - Empire State Building - Park Ave - 5th Ave Shopping - Central Park - Broadways shows and theaters We would love to help make your trip to New York a special one.... View all property information
    Location Information
    Chicago, Illinois 60611
    1 / 17
    DePaul
    4 Bedrooms, 4 Bathrooms, Sleeps 24 | Quick View
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    $500
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    • Balcony
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    • x
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    • Smoking allowed
    • Elder access
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    About this property
    Vacation in the best neighborhood in Chicago in this amazing Furnished Custom Single Family Home which is fully licensed by the City #2262746! Don't trust places which don't have a license! This home is 15 blocks from Wrigley Field, 5 blocks to the Kennedy Expressway, 6 blocks to the EL, 2... View all property information
    Location Information
    Chicago, Illinois 60614
    1 / 38
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    $90
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    • Satellite TV
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    • Internet Access
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    • Washer
    Suitability
    • Pet-friendly
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    • Child-friendly
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    • x
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    About this property
    Comfy Rental In A Neighborhood That Has Kept Its Old World Charm With The New! Artsy, Quiet And Comfortable 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.... View all property information
    Location Information
    Chicago, Illinois 60625
    1 / 21
    5 of 5 stars (1) Excellent
    Northwest Side
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Patio
    • DVD Player
    • Grill
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
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    About this property
    Our 3 bedroom cozy house feels like a cottage in the middle of the popular Avondale Neighborhood. It's perfect place for a family up to 8, we are a block from a park, Target and the river. Enjoy restaurants and a craft brewery all within in 3 blocks. Entire house with 2 bedrooms and bath... View all property information
    Location Information
    Chicago, Illinois 60618
    5 of 5 stars Reviewed October 3, 2015
    This 4 bedroom 2 full bath was very clean, well stocked, in a good neighborhood, had a very nice park for our grand children to play at within a block, great restaurants within...
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    1 / 37
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    $175
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    • Grill
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    • Smoking allowed
    • Elder access
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    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 / 4
    The Loop
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Central Heating
    • Satellite TV
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    • Pet-friendly
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    • x
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    About this property
    Experience the vibrancy of down town Chicago and delight in the modern, sleek comfort of wyndham grand Chicago river front — an intimate haven on the magnificent mile — offering chic accommodations in an exceptional setting. Just outside your door is Chicago's premier shopping avenue with over... View all property information
    Location Information
    Chicago, Illinois 60601
    1 / 9
    5 of 5 stars (1) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    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...
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    1 / 56
    5 of 5 stars (28) Excellent
    Northwest Side
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Balcony
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    • Shared Yard
    • Terrace
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
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    • Elder access
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    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
    Location Information
    Chicago, Illinois 60618
    5 of 5 stars Reviewed December 31, 2015
    quiet, warm, close to family and friends. Hanne was very friendly, helpful and very responsive to our questions, quick to help with heating. The big dining table was just perfect...
    5 of 5 stars Reviewed December 9, 2015
    Thank you Hanne for making our trip to Chicago a very comfortable experience. My family and I enjoyed staying in your apartment. The location was perfect to all the places we...
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    1 / 7
    4 of 5 stars (7) Very good
    Lincoln Park
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    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
    Location Information
    Chicago, Illinois 60614
    5 of 5 stars Reviewed August 10, 2015
    Stayed in the LPA location this past weekend and enjoyed the area tremendously. You have a park across the street and zoo just mins. down the road. The apartment itself is a cozy...
    4 of 5 stars Reviewed July 13, 2015
    Located across from Lincoln Park Zoo & Conservatory, this is an ideal location for a couple, or a family of 3. The apartment is on the 4th floor and features a large living room...
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    1 / 40
    4.5 of 5 stars (2) Very good
    Lakeview
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    Located in Chicago's East Lakeview Neighborhood (home of Wrigleyville and Boystown), our Junior 1-Bedroom Apartment provides peace & quiet while only minutes away from Chicago's best attractions. Steps from Lake Michigan and Belmont Harbor; with easy access to the lakefront, nightlife, dining,... View all property information
    Location Information
    Chicago, Illinois 60657
    4 of 5 stars Reviewed October 12, 2015
    I would give this property a 5 point review except for something that neither of our wonderful hosts could help. The elevator in the building was down for an entire day which...
    5 of 5 stars Reviewed July 16, 2015
    This was my first time using FlipKey to find a vacation rental online. I was planning a surprise weekend getaway for my husband's 40th birthday and our 9th wedding anniversary...
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    1 / 23
    5 of 5 stars (21) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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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
    Location Information
    Chicago, Illinois 60642
    5 of 5 stars Reviewed June 11, 2015
    After staying in this wonderful apartment for two of three business trips with three other colleagues, Carol let us know that she had double booked us and that she did not think...
    5 of 5 stars Reviewed May 26, 2015
    Arrived after a long flight from UK, to find that the apartment was everything we had hoped for. Greeted by Carole who made us feel very welcome and gave us very useful local...
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    1 / 27
    4.5 of 5 stars (6) Very good
    The Loop
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    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
    Location Information
    Chicago, Illinois 60605
    4 of 5 stars Reviewed May 29, 2015
    I actually rented this place for the "bike the drive" cycle ride over Memorial Day. The pictures are accurate. Tee was always available for questions, checking in, etc. a short...
    5 of 5 stars Reviewed November 7, 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...
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    2 Bedrooms, 1 Bathroom, Sleeps 7 | Quick View
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    About this property
    This historic turn of the century home has been recently remodeled while paying homage to original and period details like crown moldings and stained glass. Fresh, clean and sparkling with drop dead mid century décor. Both comfortable, roomy and stylish. There is a large fully stocked kitchen with... View all property information
    Location Information
    Chicago, Illinois 60625
    1 / 17
    5 of 5 stars (39) Excellent
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    $154
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    • Washer
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    • Elder access
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    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...
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    1 / 22
    5 of 5 stars (1) Excellent
    Near North Side
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Child-friendly
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    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
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    Northwest Side
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • x
    • x
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    • Elder access
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    About this property
    Two bedrooms, one bathroom 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. Bus... View all property information
    Location Information
    Chicago, Illinois 60618
    Lincoln Park
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    $350
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    • Child-friendly
    • x
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    • x
    About this property
    This house is ideal for a weekend visit or long stay. Every amenity is at your fingertips and every Chicago site is steps or a train away. Great modern space with eat-in chefs kitchen updated comfortable bathrooms and spacious city backyard. Perfect location for a Chicago getaway!!! Heart of... View all property information
    Location Information
    Chicago, Illinois 60614
    1 / 51
    2 of 5 stars (1) Poor
    Near North Side
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    $192
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Included is a 3-bedroom fully furnished “Old Town Chicago” condo with TWO PRIVATE BALCONIES, Flat Panel HDTVs, Fireplaces, All Utilities, All Major Appliances, WiFi, Internet, Cable, Queen Size Mattresses, Cleaning Service upon Vacating Included, Complimentary Laundry, and all of the atmosphere... View all property information
    Location Information
    Chicago, Illinois 60610
    1 / 11
    4 of 5 stars (4) Very good
    Lakeview
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    • Pet-friendly
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    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • 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
    Location Information
    Chicago, Illinois 60657
    5 of 5 stars Reviewed February 4, 2015
    Good value for the money. We enjoyed the player piano. Beds were comfortable and everything was clean.
    4 of 5 stars Reviewed July 28, 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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    Northwest Side
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    $120
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    • 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
    The Loop
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    $600
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    • Satellite TV
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Live like a Chicago local in luxury - the perfect location to take in downtown Chicago! Great for McCormick Place meetings - 10 min away! Easy access to Soldier Field, Museum Campus, Grant Park, Magnificent Mile, and steps from the L! Enjoy the perfect home-base for exploring Chicago for you and 7... View all property information
    Location Information
    Chicago, Illinois 60605
    1 / 21
    5 of 5 stars (1) Excellent
    Near North Side
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    $90
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    • x
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    • 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
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    Lakeview
    2 Bedrooms, 1 Bathroom, Sleeps 7 | Quick View
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    $350
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    Nestled in one of the more happening areas of Chicago is this super trendy 2-bedroom residence that was recently featured on Apartment Therapy! Whether you’re visiting with friends, family, or even just your pet, this household suits all. Dolled up with funk & creativity that matches the... View all property information
    Location Information
    Chicago, Illinois 60657
    Northwest Side
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    $135
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    • Washer
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    • 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
    1 / 39
    4.5 of 5 stars (15) Very good
    Northwest Side
    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    $79
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    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. We are city bee keepers as we learned they are very important for our... View all property information
    Location Information
    Chicago, Illinois 60618
    5 of 5 stars Reviewed November 18, 2015
    The bed is comfortable, the room is lovely, and the location near the bus was very convenient. The garden is a relaxing addition, even this late in the fall. I particularly...
    5 of 5 stars Reviewed October 19, 2015
    Just want to say that this location is an Excellent find and safe and secure. If you're arriving from O'Hare Intl take the blue line direct from O'Hare and within minutes you're...
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    The Loop
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    $500
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    • x
    About this property
    Modern luxury One bedroom with queen size bed Location, Location, Location Hotel type amenities. Queen size bed in your private room 900 square feet space Sleeps 4 Flatscreen TV in the livingroom Wireless Internet is not available Clean freshly-washed white sheets and white Towels waiting for... View all property information
    Location Information
    Chicago, Illinois 60616
    1 / 15
    Roscoe Village
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    $117
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    • x
    • x
    • ?
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    • Elder access
    • x
    • ?
    About this property
    Vintage rehab of classic Chicago apartment with attention to detail in all of the restored woodwork. Hardwood floors throughout. Brand new kitchen and bathroom. Radiant heat in floors and window AC units provided. 3 bedrooms, 2 have queen beds and 1 has double bed. Backyard is a beautiful respite... View all property information
    Location Information
    Chicago, Illinois 60618
    1 / 11
    5 of 5 stars (2) Excellent
    Roscoe Village
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    $229
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    • Porch
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • 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
    Location Information
    Chicago, Illinois 60618
    5 of 5 stars Reviewed August 7, 2015
    We needed a place to stay in Chicago close to family. This rental was perfect. There was more than enough room for 5 of us. It was extremely clean and very nicely decorated...
    5 of 5 stars Reviewed September 25, 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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    Lakeview
    6 Bedrooms, 2 Bathrooms, Sleeps 16 | Quick View
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    $250
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    • Terrace
    • Wi-Fi
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    • Balcony
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Lots of space in an awesome location - ONE BLOCK FROM WRIGLEY FIELD AND THE CHICAGO CUBS! This apartment sleeps 16 GUESTS over TWO FLOORS! It offers five queen beds and one double bed in their own bedrooms, plus in the semi-private alcoves in common spaces we have two queen beds, as well as two... View all property information
    Location Information
    Chicago, Illinois 60613
    Northwest Side
    2 Bedrooms, 2 Bathrooms, Sleeps 12 | Quick View
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    $299
    / Night
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    • Outdoor Dining Area
    • Porch
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    • Grill
    • Wi-Fi
    • Washer
    • Balcony
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    The space is fresh and open and can sleep 8 on individual beds and 12 if you double up on the queen mattresses. There are 2 sets of bunk beds in a small 3rd bedroom/bonus room. There are 2 living rooms which makes it easy to get away from your mates when one wants to have some quiet time or giving... View all property information
    Location Information
    Chicago, Illinois 60622
    The Loop
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    $500
    / Night
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    • Washer
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Live like a Chicago local in luxury - the perfect location to take in downtown Chicago! Great for McCormick Place meetings - 10 min away! Easy access to Soldier Field, Museum Campus, Grant Park, Magnificent Mile, and steps from the L! Enjoy the perfect home-base for exploring Chicago for you and... View all property information
    Location Information
    Chicago, Illinois 60605
    Lakeview
    3 Bedrooms, 1 Bathroom, Sleeps 8 | Quick View
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    $150
    / Night
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    • Pet-friendly
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    • x
    • x
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    • 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
    3 Bedrooms, 1 Bathroom, Sleeps 7 | Quick View
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    $125
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Have a great time in a rarely found 3 bedroom in this area. Leave the car and walk to the great restaurants and bars scene on Madison St. Only a 15 minute drive (or hop on the nearby Green Line subway station) and explore all Chicago has to offer!! You will have access to the whole first floor of... View all property information
    Location Information
    Chicago, Illinois 60130
    3 Bedrooms, 5 Bathrooms, Sleeps 5 | Quick View
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    $500
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    • Internet Access
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    • Sauna
    • Satellite TV
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • Smoking allowed
    • Elder access
    About this property
    Please note: the price for this home is for guest sleeping over. If you are hosting a party with more than the guests who are sleeping over, there is an additional fee which I work out with you once you message me. Want to host a family reunion or simply enjoy resort living for a night, a week, or... View all property information
    Location Information
    Chicago, Illinois 60101
    Lakeview
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    Owner online now
    From
    $225
    / Night
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    • 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 / 8
    3.5 of 5 stars (3) Average
    Northwest Side
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • Air Conditioning
    • Balcony
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • 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
    Location Information
    Chicago, Illinois 60630
    5 of 5 stars Reviewed August 17, 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 March 29, 2014
    Bed was a little uncomfortable and broke often. Parking was difficult. Clean apartment, ideal for a large family
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    1 / 9
    Near North Side
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
    From
    $130
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    • Washer
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    • Shared Outdoor Pool...
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Streeter Place is a remarkable new building designed for those who enjoy the very best that Chicago has to offer. From its progressive architecture to its distinctive lobby décor, Streeter Place offers a unique concept in urban living. Located in trendy Streeterville, Streeter Place is the smart... View all property information
    Location Information
    Chicago, Illinois 60611
    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.