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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.
    1 / 7
    4 of 5 stars (9) Very good
    Lincoln Park
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    1 / 15
    4.5 of 5 stars (3) Very good
    Lakeview
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    1 / 15
    4 Bedrooms, 1 Bathroom, Sleeps 17 | Quick View
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    1 / 6
    5 of 5 stars (8) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Internet Access
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    • x
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    About this property
    Beautifully furnished Three Bedroom, Two Bath. Walking distance from the lakefront, and a short bus ride to Michigan Avenue. First Floor Condominium Unit, New Oak Floors, Granite Counters, Marble Baths. Stainless Steel Brand New Appliances. In Unit, Washer, Dryer. Three Large Bedrooms. Master Bath... View all property information
    Location Information
    Chicago, Illinois
    5 of 5 stars Reviewed October 7, 2014
    The condo is all that it is advertised. The neighborhood is quiet and the condo is well appointed with all of amenities for you to enjoy your stay. The hardwood floors are a nice...
    5 of 5 stars Reviewed April 28, 2014
    This condo was wonderful. It was clean , modern and very spacious. It is at the end of a quiet street so there was no noise. It is right by Lincoln Park and it was very easy to...
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    1 / 15
    The Loop
    2 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    • Satellite TV
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    • x
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    About this property
    Exclusive tower location, feet from The Bean and the Loop L Train! Local guidebook telling you what to hit and skip! We're from Chicago. We live here. We know the place, and we have an opinion! This is your best option for an amazing base to explore Chicago, with 9 others! This is the BEST... View all property information
    Location Information
    Chicago, Illinois
    1 / 16
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    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
    1 / 17
    The Loop
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Exclusive tower location, feet from The Bean and the Loop L Train! Local guidebook telling you what to hit and skip! We re from Chicago. We live here. We know the place, and we have an opinion! This is your best option for an amazing base to explore Chicago, with 7 others! This is the BEST... View all property information
    Location Information
    Chicago, Illinois
    1 / 25
    Lakeview
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Private Yard
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    • x
    About this property
    The Lakeview neighborhood is an incredible Chicago experience! We live 3 blocks from the Brown Line stop, just a 7 minute walk from Wrigley field, right next door to some amazing Southport Corridor shopping, and terrifically close to a lot of other amazing venues. This apartment is completely... View all property information
    Location Information
    Chicago, Illinois
    1 / 12
    5 of 5 stars (9) Excellent
    Northwest Side
    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    This studio is situated in the garden of the property. Very quiet and peaceful setting. It has full bed and a jacuzzi. View all property information
    Location Information
    Chicago, Illinois
    5 of 5 stars Reviewed August 26, 2016
    We had a wonderful stay and would recommend her place to anyone. Nice, safe location and is walking distance to the subway station. Everything went extremely well thanks to Hanna.
    5 of 5 stars Reviewed July 18, 2016
    Great accommodations at the right price!!! Hanne was extremely helpful with how to get from the airport and to Wrigley, providing restaurant recommendations and answering any...
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    1 / 29
    5 of 5 stars (3) Excellent
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Patio
    • Private Yard
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    • Waterfront
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    • Pet-friendly
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    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
    5 of 5 stars Reviewed 1 week ago
    Was very please with reservation, excellent communication with owner. Very accommodating. Clean nice decor, Nice well equip kitchen. Quiet residential neighborhood
    5 of 5 stars Reviewed August 9, 2016
    I really enjoyed the condo with it stylish decor. John was so nice and accommodating. I needed a early check in and late check out and John accommodated both request. There was...
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    1 / 16
    5 of 5 stars (1) Excellent
    Lincoln Park
    2 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Washer
    • Central Heating
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    • Pet-friendly
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    • x
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    • x
    About this property
    Vacation in your own charming historic Lakeview / Lincoln Park 2-bdr & 2.5-bth Coach House with deck. Enjoy modern furnishings and amenities comfortably accommodating up to six guests. When you’re ready to explore the area, grab a bite to eat, drink, shop or play -- just a few steps out your door... View all property information
    Location Information
    Chicago, Illinois
    1 / 21
    5 of 5 stars (3) Excellent
    Northwest Side
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    • x
    About this property
    NO LARGE PARTIES!!!!great riverwest location in the heart of the city(1346 west augusta). 3 bed, 2 bath. 2800 square feet. 17 foot ceilings. perfect for entertaining. pool table, 115" movie theater,dart board, 2 blocks to bus/train line. you wont be disappointed. two bedrooms are located in the... View all property information
    Location Information
    Chicago, Illinois
    5 of 5 stars Reviewed June 7, 2016
    The photos of this property do not quite do it justice. This property was everything and more than we had hoped for. This property is way bigger than it appears in the photos...
    5 of 5 stars Reviewed March 22, 2016
    Everything went excellent! Easy to get to resturants and bars. My friends and i were very impressed with the spacious home. It was clean and ready for entertaining. Pool table and...
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    1 / 16
    The Loop
    4 Bedrooms, 4 Bathrooms, Sleeps 16 | Quick View
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    • x
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    • x
    About this property
    This is a combination of two apartments, DOWN THE HALL from each other on the same floor! Again, these apartments do not connect and are about 100 feet apart from each other. In each apartment you have: - 2 bedrooms, and 4 beds: first bedroom has 2 queen beds, second has 1 queen bed; sofa sleeper... View all property information
    Location Information
    Chicago, Illinois
    1 / 10
    5 of 5 stars (3) Excellent
    Roscoe Village
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Internet Access
    • Air Conditioning
    • Washer
    • Satellite TV
    • Porch
    • DVD Player
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • 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
    5 of 5 stars Reviewed July 4, 2016
    Very clean, modern, and responsive owner. It is located in a nice neighborhood that is close to public transportation.
    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...
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    1 / 8
    4 of 5 stars (4) Very good
    2 Bedrooms, 1 Bathroom, Sleeps 8 | Quick View
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    • Grill
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    • x
    About this property
    .One of three spacious apartments in a multi-flat historic building, located in the true artist oriented neighborhood in the heart of Chicago. Large kitchen space and a full newly remodeled bath with Jacuzzi tub and beautiful Moroccan tile. Cozy dinning room and sunny living room each with... View all property information
    Location Information
    Chicago, Illinois
    4 of 5 stars Reviewed 4 weeks ago
    The apartment is lovely and huge. It was a pleasure to stay there. The neighborhood was friendly and fascinating. We were too busy to use the tv or internet so I can't say...
    5 of 5 stars Reviewed July 12, 2016
    Would reccomend! The apartment was much bigger than I had expected. The pictures did not do it justice. Amanda was a wonderful host. We had a great time!
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    1 / 4
    4 of 5 stars (1) Very good
    Near North Side
    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    Location Information
    Chicago, Illinois
    4 of 5 stars Reviewed 4 weeks ago
    The location was perfect, great neighborhood, easy to everything. Great beach for swimming at 10 min. walk. The apartment was cosy and clean. Vanessa was very kind and she...
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    1 / 29
    The Loop
    2 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    • Air Conditioning
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    Exclusive tower location, feet from The Bean and the Loop L Train! Local guidebook telling you what to hit and skip! We're from Chicago. We live here. We know the place, and we have an opinion! This is your best option for an amazing base to explore Chicago, with 9 others! FIVE beds! Two... View all property information
    Location Information
    Chicago, Illinois
    1 / 30
    The Loop
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Air Conditioning
    • Satellite TV
    • Wi-Fi
    • Washer
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Exclusive tower location, feet from The Bean and the Loop L Train! Local guidebook telling you what to hit and skip! We're from Chicago. We live here. We know the place, and we have an opinion! This is your best option for an amazing base to explore Chicago, with 5 others! Three beds! Two... View all property information
    Location Information
    Chicago, Illinois
    1 / 14
    5 of 5 stars (1) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Washer
    • Terrace
    • Wi-Fi
    • Parking
    • Air Conditioning
    • Grill
    • Balcony
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • 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
    5 of 5 stars Reviewed May 28, 2016
    We frequently visit Chicago and find ourselves staying in the northern suburbs. This apartment rental was a find! Very classy and comfortable, room to spread out, a well stocked...
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    1 / 12
    5 of 5 stars (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Washer
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    • Grill
    • Outdoor Dining Area
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    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. Guests can enjoy their individual balconies with gas grill as well... View all property information
    Location Information
    Chicago, Illinois
    5 of 5 stars Reviewed August 26, 2015
    This apartment is specious, clean and luxurious. the living seating area has a comfortable couches and big TV. The kitchen is elegant and fully equipped. The staff are really...
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    1 / 33
    The Loop
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Pet-friendly
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    • x
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    • x
    About this property
    Exclusive tower location, feet from The Bean and the Loop L Train! Local guidebook telling you what to hit and skip! We're from Chicago. We live here. We know the place, and we have an opinion! This is your best option for an amazing base to explore Chicago, with 7 others! This is the BEST... View all property information
    Location Information
    Chicago, Illinois
    1 / 16
    Near North Side
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    About this property
    A rare opportunity to stay in Chicago's most prominent neighborhood! This fabulous apartment features 2 bedrooms and 1 bathroom, bright and spacious living room with a designated dining room. The kitchen comes fully equipped with dinnerware, flatware, pots and pans, french press coffee makers,... View all property information
    Location Information
    Chicago, Illinois
    1 / 26
    5 of 5 stars (1) Excellent
    The Loop
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Sauna
    • Hot Tub
    • Air Conditioning
    • Grill
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    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • ?
    About this property
    Unit not available for daily rental in July 4th Holiday !<BR><BR><BR>*Prices may vary depending on the season. Premium months are between April and September. <BR>*Prices negotiable based on length of stay. Please inquire and we will provide a direct quote for your stay.<BR><BR><BR>Michigan Avenue... View all property information
    Location Information
    Chicago, Illinois
    5 of 5 stars Reviewed December 9, 2014
    The view really is amazing and the apartment is well-equipped. After a little trouble getting in (which was solved by friendly staff right away), we found everything we...
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    1 / 21
    5 of 5 stars (2) Excellent
    Northwest Side
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    • Terrace
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    • x
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    About this property
    Situated feet from Logan Square itself and the (underground and quiet) Logan Square Blue Line train stop for easy 24/7 downtown & O'Hare access. We also provide free permits for convenient street parking on our block. We've lovingly preserved our 1907 home and look forward to hosting you in... View all property information
    Location Information
    Chicago, Illinois
    5 of 5 stars Reviewed July 5, 2016
    Alex is a phenomenal host. We had everything we needed and then some. This home is conveniently located by the L and Logan Square. This 1907 Greystone is perfectly decorated and...
    5 of 5 stars Reviewed March 17, 2016
    My family and I enjoyed 3 nights in this lovely home. It's a wonderful location with easy access to O'hare via the train. The house is beautifully decorated and clean. We really...
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    1 / 14
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Patio
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    • Pet-friendly
    • Child-friendly
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    • x
    About this property
    TWO-BEDROOM SUITES WITH BALCONY Open gourmet kitchen with stainless appliances Granite breakfast bar Bright and sunny living room with 10' ceilings Private balcony complete with gas grill and patio furniture King-sized bed in the master bedroom Spa-like bathroom with glass shower Two Bedroom... View all property information
    Location Information
    Chicago, Illinois
    1 / 7
    4.5 of 5 stars (7) Very good
    Northwest Side
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Shared Yard
    • Air Conditioning
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    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • 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
    5 of 5 stars Reviewed 6 days ago
    We booked this apartment quite last minute, we wanted to find somewhere relatively cheap but still nice. Hanne's apartment fitted the bill, it was very clean and comfortable...
    4 of 5 stars Reviewed 2 weeks ago
    Owner readily available but not imposing. Starter supplies of anything needed was provided . Nice neighborhood next to an elementary school. Would have preferred twin beds...
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    1 / 30
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Washer
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    • ?
    • ?
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    • x
    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
    1 / 11
    5 of 5 stars (1) Excellent
    Lincoln Square
    Studio, 1 Bathroom, Sleeps 4 | Quick View
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    • Grill
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    • Pet-friendly
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    • x
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    • x
    About this property
    Our basement studio is perfect for people who want to explore downtown yet get a feel for a true Chicago neighborhood. It feels more like your own apartment than a hotel room. There is no need for a car as we are close to the Brown Line stop. We have had this rental on airbnb for over a year and... View all property information
    Location Information
    Chicago, Illinois
    5 of 5 stars Reviewed August 16, 2016
    This property looks nice in the photos, but it was even better than we expected. The actual apartment is clean, spacious, and inviting. The bathroom and bedroom areas are large...
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    1 / 32
    5 of 5 stars (4) Excellent
    The Loop
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Balcony
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    • Shared Outdoor Pool...
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • ?
    About this property
    Unit not available for daily rental in July 4th Holiday !<BR><BR><BR>*Prices may vary depending on the season. Premium months are between April and September. <BR>*Prices negotiable based on length of stay. Please inquire and we will provide a direct quote for your stay.<BR><BR>Welcome to the LEX... View all property information
    Location Information
    Chicago, Illinois
    5 of 5 stars Reviewed November 5, 2014
    The apartment was great! The hosts were very easy to contact when needed. Even the neighbours were friendly. Good location, away from the busy city Central but still close enough...
    5 of 5 stars Reviewed October 29, 2014
    21st and Michigan, right on the bus route to go to the Downtown core and to get to the museums. Just blocks away from Chinatown. Market just across the street for meat and eggs...
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    1 / 11
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Secure Parking
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    • Pet-friendly
    • Child-friendly
    • ?
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    • x
    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
    1 / 16
    3 Bedrooms, 1 Bathroom, Sleeps 14 | Quick View
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    • x
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    About this property
    Room type: Entire home/apt Property type: Apartment Accomodate: 12+ Bedrooms: 3 Bathrooms: 1 Beds: 5 Check In: 3:00 PM Check Out: 12:00 PM Amenities Wifi Parking Kitchen utensils Price Extra People: $18 / night after the first guest . Cancellation level? Cleaning Fee: None Security Deposit:... View all property information
    Location Information
    Chicago, Illinois
    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
    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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    1 / 17
    5 of 5 stars (1) Excellent
    Lakeview
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    About this property
    This unit is an officially licensed Chicago Vacation Rental. License #2438049 There’s nothing average about this 4-bedroom, 3-bath apartment in Lakeview. Whether it’s the vast interior with plenty of elbow room for 10 people, the premier location in one of Chicago’s most vibrant neighborhoods or... View all property information
    Location Information
    Chicago, Illinois
    5 of 5 stars Reviewed 2 weeks ago
    Really nice place, excellent location,lots of bars and restaurants. With no traffic it takes a few minutes to get to the McCormick place. I recommend it
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    1 / 25
    Near North Side
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Balcony
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    About this property
    Ultimate Chicago Experience. Unbeatable South River North Location in the absolute heart of world class dining, nightlife, shopping, comedy, museums, art scene, sports bars, etc. Luxury building with doorman, insane rooftop pool+gym. You’ll love our place because of the luxury, the big comfy... View all property information
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    Chicago, Illinois
    1 / 50
    5 of 5 stars (1) Excellent
    Lincoln Park
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    Fully furnished luxury apartment in the heart of Lincoln Park next to Oz Park. Walkscore 97/100. Brand new recently fully renovated 1 bedroom apartment, bathroom with jacuzzi tub, fireplace, hardwood floors, in unit laundry, private entrance and kitchen with new appliances. 700 square... View all property information
    Location Information
    Chicago, Illinois
    5 of 5 stars Reviewed July 8, 2016
    I previously lived in Chicago for 5 years and chose this place based on the neighborhood. Not only is the Armitage and Halsted area the nicest part of Lincoln Park (with an 18...
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    1 / 25
    4 of 5 stars (1) Very good
    2 Bedrooms, 1 Bathroom, Sleeps 7 | Quick View
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    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
    4 of 5 stars Reviewed 1 week ago
    we only had one night to stay (business) - 3 adult men for convention nice area - was quiet - very clean - nice people to rent from short walk to Lincoln Square - restaurants...
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    1 / 21
    5 of 5 stars (1) Excellent
    Near North Side
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    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.<BR><BR>Every Raffaello guest room reflects an upscale European style with soothing accents, subtle earth... View all property information
    Location Information
    Chicago, Illinois
    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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    1 / 23
    5 of 5 stars (1) Excellent
    Lincoln Park
    3 Bedrooms, 3 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
    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
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    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
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    Chicago, Illinois
    1 / 30
    5 of 5 stars (40) Excellent
    Northwest Side
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    A big thank you to my guests for their great reviews. I'm so honored to have earned a 2014 Certificate of Excellence from tripadvisor! Very comfortable, private lower level of duplex. Perfect for a business traveler who doesn't want to be downtown, or a couple visiting the city for pleasure.... View all property information
    Location Information
    Chicago, Illinois
    5 of 5 stars Reviewed 4 days ago
    This spacious basement floor was very comfortable and attractive with room to relax and catch up with washing. The owner was very thoughtful providing tourist information, snacks...
    5 of 5 stars Reviewed 3 weeks ago
    Chicago..a place that we had yet to visit and was on the summer vacation bucket list. In looking for lodging, our criteria was comfort, access to public transportation and...
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    1 / 13
    DePaul, Lincoln Park
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    PLEASE NOTE: This is not a new property. We have recently left our previous management company, which had been managing this and our other 6 properties for 2+ years. Please see photos for past reviews! Our historic Lincoln Park apartment features: 4 bedrooms and 2 baths Sleeping for 8 Premier... View all property information
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    Chicago, Illinois
    1 / 40
    5 of 5 stars (4) Excellent
    Lakeview
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • ?
    • ?
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    • x
    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
    5 of 5 stars Reviewed June 2, 2016
    My wife and I are very happy with our stay. The studio is very tastefully decorated and many amenities provided. The location was perfect for our needs. We will definitely...
    5 of 5 stars Reviewed April 6, 2016
    I took my three little boys to Chicago for spring break. This location was perfect. About a five minute walk from the Belmont El station and lots of bus stops nearby. Many...
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    1 / 41
    5 of 5 stars (23) 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. If you’re heading to Chicago and looking to be near downtown but... View all property information
    Location Information
    Chicago, Illinois
    5 of 5 stars Reviewed August 13, 2016
    Wow, it's going to be hard to limit this as start to finish I can't say enough good things. I had never booked this type of vacation rental before and was very nervous that...
    5 of 5 stars Reviewed June 25, 2016
    Our family of five loved our stay at the Magic Factory. The loft is beautifully decorated with great amenities and a comfortable living room for reading or watching movies. If you...
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    1 / 39
    4.5 of 5 stars (19) Very good
    Northwest Side
    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    • ?
    • ?
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    About this property
    The studio is situated in the couch house of the property. It is 300 square feet plus the bathroom. Beautiful decorated and very quiet place with the windows facing the beautiful garden. There is a washer and dryer on side. We are city bee keepers as we learned they are very important for our... View all property information
    Location Information
    Chicago, Illinois
    5 of 5 stars Reviewed 4 days ago
    A comfortable and cozy living quarters. Not downtown but close to CTA bus/subway lines so easy to get around. Costco about a mile away! Hanne is a great host, very helpful and...
    4 of 5 stars Reviewed July 13, 2016
    We loved staying here for our quick anniversary getaway! It was a short walk to the bus and train. We definitely would stay here again!
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    1 / 23
    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    • ?
    • ?
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    • x
    About this property
    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 throughout Walk in closet Contemporary bath finishes Everything about the building has been considered;... View all property information
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    Chicago, Illinois
    1 / 25
    Near North Side
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • x
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    • 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.<BR><BR>Every Raffaello guest room reflects an upscale European style with soothing accents, subtle earth... View all property information
    Location Information
    Chicago, Illinois
    1 / 11
    4 of 5 stars (4) Very good
    Lakeview
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    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
    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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    1 / 15
    Roscoe Village
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • DVD Player
    • Porch
    • Outdoor Dining Area
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    • x
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    About this property
    Welcome to your home away from home nestled in the Village within the City – Roscoe Village in Chicago, IL. Roscoe Village is a very family friendly neighborhood. This warm and welcoming first floor unit features a high end kitchen equipped with stainless appliances & granite countertops, 1 King... View all property information
    Location Information
    Chicago, Illinois
    1 / 21
    3.5 of 5 stars (3) Average
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    One bedroom apt located in south loop Bronzeville area. Close to McCormick convention center. About 15 mins to Sox stadium.Easy access to public transportation cta bus and train. 15 mins drive to downtown. And Chinatown neighborhood.Walking distance to grocery store jewel. Walgreens .next to la... View all property information
    Location Information
    Chicago, Illinois
    5 of 5 stars Reviewed September 15, 2015
    We got lost coming into the city due to road work and Emmanuel was quick to jump in his car and come to the rescue. He helped us with our bags, gave us recommendations for bars...
    5 of 5 stars Reviewed August 15, 2015
    The host, Emmanuel, was exceptionally friendly and helpful. He was very kind and helped us to the apartment with our bags. We had arrived an hour prior to what we had said as we...
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    1 / 6
    Near South Side
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • x
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    • x
    About this property
    Welcome to my clean, comfortable and convenient apartment in South Loop! This place has everything you need to enjoy your stay. Prime location and the best view in the city! A few blocks to Grant Park, Soldier Field, McCormick Center and more. Parking available in the garage for a fee. Watch the... View all property information
    Location Information
    Chicago, Illinois
    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.