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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 / 15
    Near North Side
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    1 / 22
    Lincoln Square
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    1 / 21
    Northwest Side
    2 Bedrooms, 2 Bathrooms, Sleeps 12 | Quick View
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    1 / 6
    Near South Side
    2 Bedrooms, 2 Bathrooms, Sleeps 3 | Quick View
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    About this property
    A nice place to stay in the heart of Chicago. Beautiful home in a very convenient location. Lots of transportation, food, and entertainment, right at your fingertips. The home is also located within walking distance of McCormick Place, so if you're coming in town for a convention, this is place for... View all property information
    Location Information
    Chicago, Illinois
    1 / 97
    5 of 5 stars (1) Excellent
    Northwest Side
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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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.<BR><BR>Entire house with 2 bedrooms and bath... View all property information
    Location Information
    Chicago, Illinois
    1 / 15
    Near North Side
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    Amazing Skyline views from floor-to-ceiling windows and impeccable building amenities in a perfect location - shopping, night life, galleries and restaurants - everything at your doorstep. Luxury living at its best. Suite Details King bed in Master Bedroom and Queen Size Sofa bed in living room... View all property information
    Location Information
    Chicago, Illinois
    1 / 20
    Near North Side
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    Suite Details King bed in Master Bedroom and Queen Size Sofa bed in living room Living room and separate kitchen Floor to ceiling windows with city view Fresh Cotton Linens and Towels Provided Bamboo Wood Floors Fully Equipment Kitchen with all Major Appliances including Fridge, Stove, Oven and... View all property information
    Location Information
    Chicago, Illinois
    1 / 21
    Near North Side
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    About this property
    Amazing Skyline views from floor-to-ceiling windows and impeccable building amenities in a perfect location - shopping, night life, galleries and restaurants - everything at your doorstep. Luxury living at its best. Suite Details King bed in Master Bedroom, Queen Bed in Second Bedroom Queen Size... View all property information
    Location Information
    Chicago, Illinois
    1 / 31
    5 of 5 stars (29) Excellent
    The Loop
    2 Bedrooms, 5 Bathrooms, Sleeps 6 | Quick View
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    • Waterfront
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    About this property
    Brand new luxury 2 bedroom 2 bathroom corporate housing suite with panoramic views in a building unlike anything in Chicago!! The Resort is located in Chicago's high end neighborhood, Lakeshore East, where the Chicago River meets Lake Michigan. You will enjoy exclusive access to two full-floors... View all property information
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    Chicago, Illinois
    1 / 33
    4 Bedrooms, 4 Bathrooms, Sleeps 9 | Quick View
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    About this property
    Phoenix Golden Property 23 is close to The Beach, The golf court. You’ll love my place because of Authenticity , the coziness, the views, the location, the people, the high ceilings. My place is good for couples, solo adventurers, business travelers, families (with kids), big groups, and furry... View all property information
    Location Information
    Chicago, Illinois
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    1 / 30
    4.5 of 5 stars (7) Very good
    Rogers Park
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Residnence on the Avenue. A Spacious Vintage condo in a stunning 1928 Art Deco building on a tree lined avenue. A very quiet and secure 4 unit building with front lobby entrance. Property manager on site to answer any questions and to make sure that your stay at Residence on the Avenue is a... View all property information
    Location Information
    Chicago, Illinois
    1 / 20
    The Loop
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    Live like a Chicago local in luxury - the perfect location for tourists to take in the downtown Chicago sights! Easy access to Soldier Field, Museum Campus, Grant Park, Magnificent Mile, and steps from the L! 10 min from McCormick Place! Enjoy the perfect home-base for exploring Chicago for you... View all property information
    Location Information
    Chicago, Illinois
    1 / 15
    Private Room, 1 Bathroom, Sleeps 6 | Quick View
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    About this property
    This ad is for a PRIVATE ROOM, not the entire apartment. The room contains 2 full over full size bunk beds, desk area, a 5-shelf systems for each bed. Two individuals can sleep on the bottom bunk or a twin air mattress can be provided. Beautiful apartment ON the lakefront, two blocks from the... View all property information
    Location Information
    Chicago, Illinois
    1 / 15
    The Loop
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    Choose from Studio, Jr. One Bedroom or One Bedroom Apartments. The property is between Chicago's business district, theater district or West Loop restaurant district. Check out live shows at the Bank of America Theatre (1,950 feet) before catching a train at Ogilvie Station. Chicago O'Hare... View all property information
    Location Information
    Chicago, Illinois
    1 / 19
    West Town
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Private Yard
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    About this property
    A modern, recently renovated apartment located near public transit, with easy access to the prime downtown sites, and the hopping Noble Square and West Loop restaurant scenes. The building was just renovated, with lots of upgrades to make your visit comfortable and enjoyable. It features a... View all property information
    Location Information
    Chicago, Illinois
    1 / 10
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • Children's Pool
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    About this property
    LOCATION! LOCATION! LOCATION!<BR>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... View all property information
    Location Information
    Chicago, Illinois
    1 / 25
    The Loop
    2 Bedrooms, 6 Bathrooms, Sleeps 5 | Quick View
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    • Balcony
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    • Shared Yard
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    • x
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    • 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
    1 / 7
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Welcome to the American Eagle -- the perfect combination of powerful performance and stylish comfort. On the road, you'll enjoy an exceptional driving experience in a luxurious cockpit with Ultraleather™ seats and a wide range of state- of-the-art features. Specifications: -solar panel -15K lb.... View all property information
    Location Information
    Chicago, Illinois
    1 / 11
    4.5 of 5 stars (3) Very good
    Roscoe Village
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    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
    1 / 11
    4.5 of 5 stars (8) Very good
    Near North Side
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • ?
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    • 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
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    1 / 20
    Northwest Side
    2 Bedrooms, 1 Bathroom, Sleeps 3 | Quick View
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    • Central Heating
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    • Pet-friendly
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    • x
    • x
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    • x
    About this property
    Booked through May 1. Thank you! Enjoy a great urban experience staying in The ALONZO HOUSE, an amazing art filled loft in the Ukrainian Village, Chicago's 1st Ward. This beautiful three story Victorian house was built in 1885, in the heart of Ukrainian village/West town, one of the oldest... View all property information
    Location Information
    Chicago, Illinois
    1 / 10
    Lakeview
    4 Bedrooms, 3 Bathrooms, Sleeps 11 | Quick View
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    About this property
    This unit is an officially licensed Chicago Vacation Rental. License #2438048 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 11 people, the premier location in one of Chicago’s most vibrant neighborhoods or... View all property information
    Location Information
    Chicago, Illinois
    1 / 19
    Lakeview
    6 Bedrooms, 2 Bathrooms, Sleeps 16 | Quick View
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    • Terrace
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    • x
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    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
    1 / 11
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    About this property
    Welcome to our modern, comfortable apt. We are conveniently located blocks from Pink Line train. We live in a fantastic neighborhood full of art, great food and many convenient grocery stores. 5 minutes from Rush Hospital on Pink line train. Our neighborhood has a family friendly vibe full of art... View all property information
    Location Information
    Chicago, Illinois
    1 / 13
    Lincoln Park
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    Lovely bright garden apartment in Lincoln Park/ Depaul residence. One bedroom, oversized bath, fully equipped kitchen, fireplace, W/D, AC, cable TV, and Wifi included. Located in a wonderful neighborhood with ample street parking and is walking distance to everything in Lincoln Park including el... View all property information
    Location Information
    Chicago, Illinois
    1 / 15
    Near North Side
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • ?
    About this property
    Amazing Skyline views from floor-to-ceiling windows and impeccable building amenities in a perfect location - shopping, night life, galleries and restaurants - everything at your doorstep. Luxury living at its best. Suite Details King bed in Master Bedroom, Queen Bed in Second Bedroom Queen Size... View all property information
    Location Information
    Chicago, Illinois
    1 / 4
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • x
    About this property
    Heart of Pilsen walking distance to grocery stores, art galleries, top Mexican restaurants, little Italy nearby, universities, cafe shops, downtown area 5 min away, medical district 3 minutes away, cozy momma & papa restaurants half block away, sauna included with stay, access to kitchen available,... View all property information
    Location Information
    Chicago, Illinois
    1 / 52
    5 of 5 stars (34) Excellent
    Southwest Side
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    About this property
    We have two really incredible vacation rental apartments that are a great value. We have 8 years of 5 star rentals at this and other sites. Our rentals are located very close to our Downtown city center and very close to everything that people come to Chicago for. The view in our first picture... View all property information
    Location Information
    Chicago, Illinois
    1 / 53
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • x
    About this property
    Conveniently, we are just a few minutes away from McCormick Place, Illinois Institute of Technology, Chinatown, U.S. Cellular Field, the Magnificent Mile, Millennium Park, Grant Park, Willis Tower, and all of the city’s most popular attractions via the Chicago Transit Authority Blue and Red Line... View all property information
    Location Information
    Chicago, Illinois
    1 / 17
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    About this property
    Sunny and updated 2BR/1BA apartment in 2 unit brick building in Edgewater. Perfect location - 5 min to train downtown, 9 min walk to beach and Lakefront trail. Quiet street with easy access to grocery stores, shops and all Chicago attractions. Second floor unit with hardwood floor throughout. Both... View all property information
    Location Information
    Chicago, Illinois
    1 / 27
    Near North Side
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • x
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    • x
    About this property
    Right in the heart of Chicago's premier Streeterville neighborhood. Famous landmarks such as Michigan Ave, Navy Pier, Millennium Park and Magnificent Mile are a short stroll away. Excellent location coupled with luxury living at its finest. Suite Details King bed in Master Bedroom, Queen size bed... View all property information
    Location Information
    Chicago, Illinois
    1 / 27
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • x
    • ?
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    • x
    About this property
    Right in the heart of Chicago's premier Streeterville neighborhood. Famous landmarks such as Michigan Ave, Navy Pier, Millennium Park and Magnificent Mile are a short stroll away. Excellent location coupled with luxury living at its finest. Suite Details King bed in Master Bedroom, Queen size bed... View all property information
    Location Information
    Chicago, Illinois
    1 / 26
    Near North Side
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    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>MSG ME WITH ANY... View all property information
    Location Information
    Chicago, Illinois
    1 / 31
    The Loop
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    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>30 days minimum... View all property information
    Location Information
    Chicago, Illinois
    1 / 17
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • x
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    • x
    About this property
    Chicago, with its towering skyscrapers and sandy beaches, is one of the most visited cities in the Midwest, and it’s easy to see why. From the lively nightlife, to world class shopping and dining, museums, festivals, and sports, this vivacious city has something for everyone. While you’re visiting... View all property information
    Location Information
    Chicago, Illinois
    1 / 12
    Northwest Side
    2 Bedrooms, 1 Bathroom, Sleeps 7 | Quick View
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    About this property
    Great apartment in a house on a tree lined street between O'Hare and the Loop/Downtown, near Blue Line Subway and Highway. Huge living/dining areas. Bedrooms have comfortable queen size beds. Living room has a sleeper sofa. Dining room has a table for 4. Perfect set up for a group. Fast Wifi and... View all property information
    Location Information
    Chicago, Illinois
    1 / 16
    5 of 5 stars (1) Excellent
    Northwest Side, West Town
    2 Bedrooms, 1 Bathroom, Sleeps 3 | Quick View
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    About this property
    Great 2b, 1 bath apartment in the walkable Ukrainian Village! Close to groceries, restaurants, shopping, clubs, public transportation, and easy access to downtown and the lake frowalk out of your apartment to the garden in the backyard, and enjoy your coffee, or watch the kids playing in the... View all property information
    Location Information
    Chicago, Illinois
    1 / 52
    4 of 5 stars (10) Very good
    DePaul
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    About this property
    BEFORE YOU BOOK PLEASE NOTE THERE IS A 4 NIGHT MINIMUM FROM MAY THROUGH OCTOBER, WITH A 5 NIGHT MINIMUM FOR HOLIDAY WEEKENDS AND SPECIAL EVENT WEEKENDS. PLEASE DO NOT AUTOBOOK FOR PERIODS SHORTER THAN WHAT IS REQUIRED AS THE BOOKING WILL NOT BE HONORED. PLEASE EMAIL OR CALL WITH ANY QUESTIONS.... View all property information
    Location Information
    Chicago, Illinois
    1 / 24
    Lakeview
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • ?
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    • 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
    1 / 18
    Lakeview
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Satellite TV
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Located in Chicago's New East Side neighborhood, The ParkShore symbolizes gracious city living at its best. Built in 1991, The ParkShore is a 56-story, 483-unit high-rise. This condo is located on the 52nd floor. The views of Lake Michigan, the Chicago River, Navy Pier and the Chicago Skyline are... View all property information
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    Chicago, Illinois
    1 / 16
    Near North Side
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • Hot Tub
    • Sauna
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    • Pet-friendly
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    • Smoking allowed
    • x
    About this property
    Right in the heart of Chicago's premier Streeterville neighborhood. Famous landmarks such as Michigan Ave, Navy Pier, Millennium Park and Magnificent Mile are a short stroll away. Excellent location coupled with luxury living at its finest. Suite Details King bed in Master Bedroom, Queen size bed... View all property information
    Location Information
    Chicago, Illinois
    1 / 21
    2 Bedrooms, 1 Bathroom, Sleeps 8 | Quick View
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    • Outdoor Dining Area
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    We have a great 2 bedroom apt minutes from Rush hospital and UIC. Minutes from Chinatown Square, McCormick and the loop. Pink Line train is very easily accessible from our home which will get you anywhere in the city. Our Neighborhood is very lively full of families, kids, art, great food and many... View all property information
    Location Information
    Chicago, Illinois
    1 / 11
    2 of 5 stars (1) Poor
    Rogers Park
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
    other travelers have booked this property
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • 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
    1 / 5
    Near North Side
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    • Shared Outdoor Pool...
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    • Pet-friendly
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    • x
    • x
    • Smoking allowed
    • x
    About this property
    Looking for luxury apartments in Chicago? Look no further than my 2 Bedroom unit, located in Chicago's highly desired Gold Coast neighborhood. Features include a swimming pool with a sundeck, fitness room, valet dry cleaners, business center with Wi-Fi, laundry facility. RED LINE TRAIN NEXT DOOR.... View all property information
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    Chicago, Illinois
    1 / 20
    Lakeview
    5 Bedrooms, 3 Bathrooms, Sleeps 14 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    This 5 bedroom apartment sleeps 14, an oasis in the midst of all the excitement that Wrigleyville and Chicago have to offer! Walk to Wrigley Field, CTA Red Line, nightlife, bars, restaurants, and lots more! Perfect for families and large groups! Lots of space in an awesome location - and a... View all property information
    Location Information
    Chicago, Illinois
    1 / 10
    The Loop
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • x
    • x
    • Smoking allowed
    • x
    About this property
    ***AVAILABILITY SUBJECT TO CHANGE WITHOUT NOTICE. RATES ARE SUBJECT TO CHANGE UNTIL RESERVATION IS CONFIRMED*** Experience the vibrancy of downtown Chicago while enjoying the modern comfort of the Wyndham Grand Chicago Riverfront. True to its name, this luxurious Wyndham property overlooks the... View all property information
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    Chicago, Illinois
    1 / 17
    Southwest Side
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    • Satellite TV
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Experience top quality in a spacious apt during your next visit to beautiful Chicago!. Features 2 bedroom & 2 bathroom with 2 separate living rooms, gourmet kitchen and laundry room. Located in quiet neighborhood only 10 mins away from the heart of downtown for an affordable price The spacious... View all property information
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    Chicago, Illinois
    1 / 39
    Northwest Side
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    • x
    • ?
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    • x
    About this property
    Our single-family home has an extra bedroom for short and long-term lodgers. Located a block away from the California stop on Blue Line Subway (40 minutes to O'Hare & 15 minutes to downtown), our home is in the heart of popular, vibrant and buzzing Logan Square, a neighborhood packed with... View all property information
    Location Information
    Chicago, Illinois
    1 / 18
    Northwest Side
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Shared Yard
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Here's your spot for a comfortable stay in Chicago! Enjoy some of the best neighborhoods in the city with fast and easy access to whatever interests you: outdoors and parks, restaurants and nightlife, museums and galleries, architecture and landscapes. Whatever you love, you'll find in our... View all property information
    Location Information
    Chicago, Illinois
    1 / 7
    Near North Side
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Pet-friendly
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    • ?
    • Smoking allowed
    • x
    About this property
    Suite Home Chicago at Grand Plaza offers fully furnished apartments. Rates include housekeeping, all taxes, high speed wireless internet, expanded cable, all utilities, linens, towels, and first class customer service. Situated in the middle of the very popular River North neighborhood, Grand... View all property information
    Location Information
    Chicago, Illinois