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Holiday Rentals in Chicago, IL

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    Travellers to Chicago are booking September dates now. Secure your holiday rental today, and have the perfect trip.
    1 / 59
    Lakeview
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    1 / 14
    DePaul, Lincoln Park
    4 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    1 / 18
    Northwest Side
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    1 / 21
    2 Bedrooms, 1 Bathroom, Sleeps 8 | Quick View
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    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 60608
    1 / 30
    5 of 5 stars (37) 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 60625
    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 60616
    1 / 14
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    Brilliantly sunny top floor of historic two flat on a lovely tree lined street. The well appointed apartment is beautiful. It has been furnished very thoughtfully, with comfort and simplicity in mind - It boasts of old world charm along with modern conveniences. Steps away from the quaint... View all property information
    Location Information
    Chicago, Illinois 60640
    1 / 15
    4 Bedrooms, 1 Bathroom, Sleeps 17 | Quick View
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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 60608
    1 / 9
    4.5 of 5 stars (2) Very good
    Lakeview
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    This is a beautiful garden unit. It comes fully furnished with a queen size bed plus a pull-out couch. Plenty of sitting room, updated bathroom, does not have kitchen but does have small fridge, microwave and coffee maker. The location is ideal, being close to the city and still in a quiet... View all property information
    Location Information
    Chicago, Illinois 60657
    1 / 8
    3.5 of 5 stars (4) Average
    The Loop
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    This beautifully furnished Studio/ 1 BA apartment sits in downtown Chicago's premiere location, right on Michigan Avenue, as well as steps from all the best shopping, restaurants, and entertainment Chicago has to offer. This apartment has a queen-sized, single bed, and a large sofa to comfortably... View all property information
    Location Information
    Chicago, Illinois 60605
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    1 / 11
    5 of 5 stars (1) Excellent
    Lincoln Square
    Studio, 1 Bathroom, Sleeps 4 | Quick View
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    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. Our rental space has its own entrance and is separate... View all property information
    Location Information
    Chicago, Illinois 60625
    1 / 11
    The Loop
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    Magnificent mile 1 brm convertible apt off Michigan Avenue in hotel district featuring 24 hr doorman, rooftop gym, sundeck, business ctr and garden patio. Your neighbors are the Hyatt, Fairmont and Radisson Blue. Gym, sundeck on rooftop 48th floor. Insane winter reductions!! North side prices in... View all property information
    Location Information
    Chicago, Illinois 60601
    1 / 7
    3.5 of 5 stars (2) Average
    1 Bedroom, 1 Bathroom, Sleeps 6 | Quick View
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    • Private Garden
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    About this property
    Last min cancellation trying get my renter some of her deposit back for her!In the heart of Pilsen in Chicago's Artist community. Beautiful city views. Unique space in Chicago's Historic district. One block from Thalia Hall. Fire Place, Brand new Bathroom/custom tile. Restored original Red hardwood... View all property information
    Location Information
    Chicago, Illinois 60608
    1 / 18
    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
    1 / 18
    Lakeview
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Washer
    • Balcony
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    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
    Location Information
    Chicago, Illinois 60601
    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 60605
    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 606016
    1 / 12
    5 of 5 stars (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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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. Guests can enjoy their individual balconies with gas grill as well... View all property information
    Location Information
    Chicago, Illinois 60640
    1 / 7
    5 of 5 stars (1) Excellent
    Near North Side
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    It is a great location in Downtown Chicago. It is close to everywhere. Opposite side is Northwestern Memorial Hospital , following building is Ann Lurie Children's Hospital. It is walking distance to Magnificent Mile (Michigan Ave.) , Navy Pier. There are restaurants , markets all around. Welcome... View all property information
    Location Information
    Chicago, Illinois 60611
    1 / 19
    Lakeview
    4 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    • Balcony
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    • Pet-friendly
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    About this property
    Luxury Wrigleyville Vacation Rental Condo - 4 Bedroom / 3 Bath / Sleeps 12 - 3 Blocks from Wrigley Field - Newly Constructed Building - High End Luxury Finishes - 1st floor unit, 2 level, duplex down. Sleeps up to 12 with the addition of 2 queen size air mattresses. - 3 - 50' plasma tvs,... View all property information
    Location Information
    Chicago, Illinois 60657
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    1 / 25
    2 Bedrooms, 1 Bathroom, Sleeps 7 | Quick View
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    • x
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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 / 6
    3.5 of 5 stars (3) Average
    Private Room, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    Charming, roomy one bedroom , with open kitchen and living space. This recently refurbished loft-style apartment gives visitors to Chicago a chance to visit and explore whist enjoying the comforts of modern living. Hardwood floor, and ceramic tiles in kitchen and bathroom. Plenty of sitting... View all property information
    Location Information
    Chicago, Illinois 60618
    1 / 9
    5 of 5 stars (1) Excellent
    Northwest Side
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    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 / 12
    5 of 5 stars (7) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Satellite TV
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    • Waterfront
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    • x
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    • x
    About this property
    Elegant 1 bedroom apartment on N Lake Shore Drive,10 min away from Michigan Avenue, Northwestern Memorial Hospital, 25 min by bus to Millenium Park and the Art Institute. Fully furnished, 900 sq ft,beautiful oak floors, high ceilings, custom architectural details.Perfect residential accommodations... View all property information
    Location Information
    Chicago, Illinois 60613
    1 / 10
    Lakeview
    4 Bedrooms, 2 Bathrooms, Sleeps 10 | 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 updated Lincoln Park apartment features: 4 bedrooms and 2 baths Sleeping for 8 Premier... View all property information
    Location Information
    Chicago, Illinois 60657
    1 / 12
    Near North Side
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • x
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    About this property
    Modern 3 story townhouse with private penthouse to Garden Roof Top. Designer Town House has 100% Brazilian Cherry wood floors onyx fire place ,deisigner kitchen-stainless steel applicances/garnite counters/built in kitchen seating area with convenient outdoor balcony equipped with grill/seating for... View all property information
    Location Information
    Chicago, Illinois 60610
    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 60614
    1 / 40
    The Loop
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Grill
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    • x
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    About this property
    Take in views of the entire city from this massive Iconic skyscraper in downtown Chicago. Experience elite luxury and comfort from your own perch overlooking the Chicago skyline. This building is equipped with full gym, indoor outdoor pools and hot tubs, dry and wet saunas, and on-site 5-star... View all property information
    Location Information
    Chicago, Illinois 60601
    1 / 15
    Near North Side
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    Ref # 364647 Because we focus on monthly rentals, we do not accept bookings with a gap between move in date and availability date. We generally require move in dates to be within 7 days of the availability date. Experience ease and comfort by staying in this beautifully furnished one bedroom luxury... View all property information
    Location Information
    Chicago, Illinois
    1 / 21
    5 of 5 stars (2) Excellent
    Northwest Side
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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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 60647
    1 / 11
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    About this property
    Stay at our cool garden apt in the heart of Chicago, (Pilsen). We are centrally located in a fun, lively neighborhood just ten minutes from downtown and McCormick Place. We are also across the street from a huge park with pool and gym. Our neighborhood is a very great neighborhood with fantastic... View all property information
    Location Information
    Chicago, Illinois 60608
    1 / 51
    3.5 of 5 stars (3) Average
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • ?
    About this property
    Unit not available for daily rental in July 4th Holiday ! 1 week minimum<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... View all property information
    Location Information
    Chicago, Illinois 60601
    1 / 22
    5 of 5 stars (1) Excellent
    Near North Side
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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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
    1 / 15
    The Loop
    2 Bedrooms, 2 Bathrooms, Sleeps 10 | 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 9 others! This is the BEST... View all property information
    Location Information
    Chicago, Illinois 60602
    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 60613
    1 / 9
    3 of 5 stars (1) Average
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Large, roomy two bedroom loft like apartment tastefully appointed and furnished. Hardwood floors and ceramic tiles in kitchen and bathroom. Plenty of sitting room with large screen TV, fireplace and free WiFi. Two full bedrooms, one with a king sized and the other with a queen sized bed. You... View all property information
    Location Information
    Chicago, Illinois 60618
    1 / 10
    Rogers Park
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Private Garden
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    • x
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    About this property
    This is the only Frank Lloyd Wright designed home available as a venue or vacation rental in the city of Chicago. The home was designated a Chicago Landmark property and has been historically and accurately renovated to FLW's original design. The tea house and gardens are also available (separate... View all property information
    Location Information
    Chicago, Illinois 60626
    1 / 15
    4.5 of 5 stars (5) Very good
    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    Furnished Studio. Double bed, full bath, and full kitchen.<BR><BR>Unique location. You don't need a car living here. Plenty of transit options. A couple of blocks to Red line train station. Direct express bus to Chicago downtown stops right around the corner. 20 minutes to the city center by... View all property information
    Location Information
    Chicago, Illinois 60640
    1 / 15
    Private Room, 1 Bathroom, Sleeps 6 | Quick View
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    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
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    Chicago, Illinois 60649
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    4 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    Just a couple blocks from the United Center this splendidly rehabbed 3 story townhouse is the place for your group to stay when visiting Chicago. Plenty of space for everyone! Full kitchen and dining room. 4 Bedrooms, and an additional two sleeper sofas. 2.5 Baths and two big living areas. Garage... View all property information
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    Chicago, Illinois 60612
    1 / 33
    4 Bedrooms, 4 Bathrooms, Sleeps 9 | Quick View
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    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 53211
    1 / 11
    5 of 5 stars (1) Excellent
    Northwest Side
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    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
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    Chicago, Illinois 60707
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    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
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    Chicago, Illinois 60640
    1 / 97
    5 of 5 stars (1) Excellent
    Northwest Side
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    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
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    Chicago, Illinois 60618
    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 60601
    1 / 17
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    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
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    Chicago, Illinois 60660
    1 / 27
    4.5 of 5 stars (6) Very good
    The Loop
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    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
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    Chicago, Illinois 60605
    1 / 7
    5 of 5 stars (1) Excellent
    Northwest Side
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    Thank you viewing this listing. I am offering a fully furnished two bedroom, one bathroom garden view unit. The condo 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
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    Chicago, Illinois 60707
    1 / 17
    Near North Side
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    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 60654
    1 / 23
    5 of 5 stars (1) Excellent
    Lincoln Park
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    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