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Weekend Getaways in Chicago - Vacation Rentals

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    $79
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    1 / 12
    5 of 5 stars (6) Excellent
    Northwest Side
    Studio, 1 Bathroom, Sleeps 2
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    Near North Side
    1 Bedroom, 1 Bathroom, Sleeps 4
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    $4,200
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    The Loop
    1 Bedroom, 1 Bathroom, Sleeps 3
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    1 / 14
    4.5 of 5 stars (13) Very good
    Northwest Side
    Studio, 1 Bathroom, Sleeps 2
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    • Air Conditioning
    • Satellite TV
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    • Linens Provided
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
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    • Smoking allowed
    • Elder access
    • x
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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
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    Location Information
    Chicago, Illinois 60618
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    $200
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    1 / 8
    3.5 of 5 stars (3) Average
    Northwest Side
    2 Bedrooms, 2 Bathrooms, Sleeps 5
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    • TV
    • Balcony
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    About this property
    This very affordable two bedroom, two bathroom apartment can sleep up to six guests. There are queen sized beds in each bedroom and a pull out couch in the living room. With features including: a breakfast table in the well-appointed kitchen; dining room; comfortable living room; a balcony;... View all property information
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    Location Information
    Chicago, Illinois 60630
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    $205
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    1 / 12
    5 of 5 stars (2) Excellent
    Gold Coast, Near North Side
    1 Bedroom, 1 Bathroom, Sleeps 4
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    • Satellite TV
    • Air Conditioning
    • Refrigerator
    • DVD Player
    • Internet Access
    • Fireplace
    • Stove
    • Porch
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Enjoy this fabulous Chicago brownstone vacation rental located in the heart of the exclusive Gold Coast neighborhood. This downtown vacation rental gives you access to all the amazing features of downtown Chicago. Enjoy the shopping, eateries and entertainment that you can only find here. A... View all property information
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    Location Information
    Chicago, Illinois 60611
    From
    $350
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    2 Bedrooms, 2 Bathrooms, Sleeps 5
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    • Washer
    • Dryer
    • Air Conditioning
    • Hot Tub
    • Satellite TV
    • Sauna
    • Elevator/Lift access
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • Smoking allowed
    • Elder access
    • x
    About this property
    Location. Situated in the heart of Chicago, is within walking distance of American Medical Association Headquarters, Wrigley Building, and Tribune Tower. Also nearby are Hancock Tower and Millennium Park. Property Features. The front desk is open 24 hours a day. Guest parking is available for... View all property information
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    Location Information
    Chicago, Illinois 60654
    From
    $250
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    2 Bedrooms, 2 Bathrooms, Sleeps 6
    other travelers have booked this property
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    • Fireplace
    • Washer
    • Air Conditioning
    • Refrigerator
    • Hot Tub
    • Internet Access
    • Satellite TV
    • Stove
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    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
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    Location Information
    Chicago, Illinois 60618
    From
    $150
    / Night
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    2 Bedrooms, 1 Bathroom, Sleeps 4
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    Amenities & Details
    • Linens Provided
    • Refrigerator
    • Stove
    • Air Conditioning
    • Dishwasher
    • Wi-Fi
    • Dryer
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    The definition of the perfect location. Lincoln Park one of Chicago's most prestigious neighborhoods is central to just about everything! A typical day might start with a trip to Chicago's best farmers market (Green City Market) just a few blocks away. After breakfast spend some time walking around... View all property information
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    Location Information
    Chicago, Illinois 60614
    From
    $308
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    1 / 21
    5 of 5 stars (54) Excellent
    Lakeview
    3 Bedrooms, 1 Bathroom, Sleeps 6
    Overview Reviews (54) Make Inquiry
    Overview Reviews (54)
    Amenities & Details
    • Washer
    • Satellite TV
    • Deck
    • Internet Access
    • Air Conditioning
    • DVD Player
    • Fireplace
    • Dryer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Make Inquiry
    Location Information
    Chicago, Illinois 60657
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    From
    $200
    / Night
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    The Loop
    2 Bedrooms, 1 Bathroom, Sleeps 8
    other travelers have booked this property
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    Amenities & Details
    • Dryer
    • Dishwasher
    • Linens Provided
    • Refrigerator
    • Air Conditioning
    • Wi-Fi
    • TV
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    This is a one bedroom loft with the living-room converted into a second bedroom. It has two beds in the bedroom and the living-room has a bunk bed. 800 square feet 32″ Flat-screen TV Wireless Internet-5 MPBS This luxury condominium is conveniently located one block to McCormick Place with easy... View all property information
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    Location Information
    Chicago, Illinois 60616
    From
    $348
    / Night
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    1 / 10
    5 of 5 stars (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6
    Overview Reviews (1) Make Inquiry
    Overview Reviews (1)
    Amenities & Details
    • Gym
    • Internet Access
    • Air Conditioning
    • Grill
    • Elevator/Lift access
    • Washer
    • Dryer
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Live like a local and save! Book now to take advantage of discounted fall rates! Beautiful 2 Bedroom unit in boutique luxury building with 24 hour concierge service. Located in the wonderful and historic Andersonville neighborhood, The Guesthouse Chicago vacation rental encourages you to live... View all property information
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    Location Information
    Chicago, Illinois 60640
    From
    $190
    / Night
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    1 / 21
    4.5 of 5 stars (17) Very good
    West Town
    3 Bedrooms, 2 Bathrooms, Sleeps 8
    other travelers have booked this property
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    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • x
    About this property
    Situated on quiet side street across from 19c. church, steps from populars bars, restaurants, and public transportation. The apartment occupies the top two floors with large private roof top deck with magnificent views of Chicago skyline. First level contains large kitchen, living room/dining... View all property information
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    Location Information
    Chicago, Illinois 60642
    From
    $159
    / Night
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    1 / 30
    4.5 of 5 stars (6) Very good
    Rogers Park
    2 Bedrooms, 2 Bathrooms, Sleeps 6
    other traveler has booked this property
    Overview Reviews (6) Make Inquiry
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    Amenities & Details
    • DVD Player
    • Hot Tub
    • Internet Access
    • Air Conditioning
    • Dryer
    • Washer
    • Satellite TV
    • Fireplace
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    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
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    Location Information
    Chicago, Illinois 60645
    From
    $359
    / Night
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    1 / 26
    4 of 5 stars (1) Very good
    Lakeview
    3 Bedrooms, 1 Bathroom, Sleeps 6
    Overview Reviews (1) Make Inquiry
    Overview Reviews (1)
    Amenities & Details
    • Washer
    • Dryer
    • Internet Access
    • Deck
    • Stereo System
    • Satellite TV
    • Air Conditioning
    • Patio
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Intimate & cozy and filled with character! You'll be so comfortable you'll never want to leave! Walk in to the home and the first thing you notice is nothing has been taken for granted. You’ll be engulfed in warm inviting hues. The beauty & integrity of the historic Greystone recaptured;... View all property information
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    Location Information
    Chicago, Illinois 60657
    From
    $466
    / Night
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    1 / 27
    5 of 5 stars (20) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8
    Overview Reviews (20) Make Inquiry
    Overview Reviews (20)
    Amenities & Details
    • Fireplace
    • DVD Player
    • Stereo System
    • Internet Access
    • Air Conditioning
    • Deck
    • Elevator/Lift access
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Want to live like a local while staying in Chicago and save? Reserve now and take advantage of discounted rates this fall! Our Chicago vacation rental offers an affordable and comfortable place to lay your head during your visit to our city! A family-owned, Chicago boutique vacation rental... View all property information
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    Location Information
    Chicago, Illinois 60640
    From
    $195
    / Night
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    1 / 18
    3.5 of 5 stars (5) Average
    Rogers Park
    3 Bedrooms, 2 Bathrooms, Sleeps 8
    other travelers have booked this property
    Overview Reviews (5) Make Inquiry
    Overview Reviews (5)
    Amenities & Details
    • Fireplace
    • Dryer
    • Internet Access
    • Satellite TV
    • Air Conditioning
    • DVD Player
    • Grill
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Residence on the Avenue. A Spacious 2000sq.ft. condo in a stunning blonde brick/limestone 1928 building on a tree lined avenue. A very quiet and secure 4 unit building with front lobby entrance. The entrance boxwood garden which is enclosed by beautiful wrought iron fencing is a hint of what awaits... View all property information
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    Location Information
    Chicago, Illinois 60645
    From
    $838
    / Night
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    1 / 37
    Lakeview
    6 Bedrooms, 3 Bathrooms, Sleeps 14
    Overview Make Inquiry
    Overview
    Amenities & Details
    • Garage
    • Patio
    • Internet Access
    • Balcony
    • Air Conditioning
    • Porch
    • Linens Provided
    • Deck
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    CHICAGO GUEST HOUSE Tripadvisor Certificate of Excellence 2014 5.0 of 5 stars --128 Reviews on TRIPADVISOR Ranked #1 of 51 Specialty Lodging in Chicago! ************************* Beautiful & Spacious--Filled With Charm & Character! The Guest House on Newport Avenue has two apartments in the... View all property information
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    Location Information
    Chicago, Illinois 60657
    From
    $190
    / Night
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    1 / 7
    Gold Coast, Near North Side
    Studio, 1 Bathroom, Sleeps 2
    Overview Make Inquiry
    Overview
    Amenities & Details
    • Air Conditioning
    • Washer
    • TV
    • Gym
    • DVD Player
    • Wi-Fi
    • Elevator/Lift access
    • Housekeeping...
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    This luxurious building is located conveniently close to Michigan Avenue, Rush Street and the lake. Take advantage of Chicago's wonderful restaurants, shopping and nightlife. •Breathtaking Views •Spacious Balconies •24 Hour Doorman •Fully Equipped Fitness Center •Rooftop Sundeck •Supermarket with... View all property information
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    Location Information
    Chicago, Illinois 60611
    From
    $348
    / Night
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    1 / 18
    5 of 5 stars (2) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6
    Overview Reviews (2) Make Inquiry
    Overview Reviews (2)
    Amenities & Details
    • DVD Player
    • Deck
    • Satellite TV
    • Air Conditioning
    • Elevator/Lift access
    • Stereo System
    • Fireplace
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Want to live like a local while staying in Chicago and save? Reserve now and take advantage of fall savings! Our Chicago vacation rental offers an affordable and comfortable place to lay your head during your visit to our city! A family-owned, Chicago boutique property near Wrigley Field, The... View all property information
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    Location Information
    Chicago, Illinois 60640
    Get the List
    From
    $599
    / Night
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    1 / 11
    Near North Side
    2 Bedrooms, 2 Bathrooms, Sleeps 7
    Overview Make Inquiry
    Overview
    Amenities & Details
    • Satellite TV
    • Shared Indoor Pool
    • Central Heating
    • Sauna
    • Internet Access
    • Washer
    • Gym
    • Elevator/Lift access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • ?
    About this property
    Welcome to the luxury and tranquility of the Chicago Penthouse Suite, a rental residence with elegant condominium-quality interiors. The suite boasts 9.5' ceilings, floor to ceiling windows, a private balcony with grill, granite bath and kitchen, beautiful cabinetry, and stainless steel kitchen... View all property information
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    Location Information
    Chicago, Illinois 60654
    From
    $449
    / Night
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    1 / 32
    5 of 5 stars (27) Excellent
    The Loop
    2 Bedrooms, 2 Bathrooms, Sleeps 6
    Overview Reviews (27) Make Inquiry
    Overview Reviews (27)
    Amenities & Details
    • Shared Indoor Pool
    • Hot Tub
    • Waterfront
    • Sauna
    • Air Conditioning
    • Housekeeping...
    • Wi-Fi
    • Ping Pong Table
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • x
    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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    Location Information
    Chicago, Illinois 60601
    From
    $300
    / Night
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    1 / 7
    5 of 5 stars (1) Excellent
    Near North Side
    2 Bedrooms, 2 Bathrooms, Sleeps 6
    Overview Reviews (1) Make Inquiry
    Overview Reviews (1)
    Amenities & Details
    • Linens Provided
    • Towels Provided
    • Soap/Shampoo...
    • Internet Access
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Top floor unit in historic Old Town Neighborhood. Close to shopping, Brown Line El stop. Downtown . And North Avenue Beach! We do allow 1-2 nights stays Monday-Thursday with a cleaning fee. Over any weekend we have minimum nights stay of 3,4,5 or 6 nights. Please ask how many nights your... View all property information
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    Location Information
    Chicago, Illinois 60614
    From
    $325
    / Night
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    1 / 7
    5 of 5 stars (3) Excellent
    Near North Side
    4 Bedrooms, 2 Bathrooms, Sleeps 10
    Overview Reviews (3) Make Inquiry
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    • Soap/Shampoo...
    • Towels Provided
    • Fireplace
    • Linens Provided
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Our newly rehabbed and fully furnished unit has 4 bedrooms, 2 bathrooms and sleeps 10. Whether you are planning a weekend excursion, business trip or need a comfortable place to stay for family or friends. We are in a great family neighborhood close to downtown. You can walk to the Zoo and North... View all property information
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    Location Information
    Chicago, Illinois 60614
    From
    $299
    / Night
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    1 / 29
    4.5 of 5 stars (4) Very good
    DePaul
    6 Bedrooms, 7 Bathrooms, Sleeps 20
    Overview Reviews (4) Make Inquiry
    Overview Reviews (4)
    Amenities & Details
    • Deck
    • Fireplace
    • Patio
    • Internet Access
    • Hot Tub
    • Air Conditioning
    • Satellite TV
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Whether you are a couple looking for a romantic weekend getaway or an executive looking for a place to unwind during a hectic business trip, the warm and spacious surroundings of this magnificently appointed Tuscan style villa will melt the stresses of the world away. With a total of 6 starting at... View all property information
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    Location Information
    Chicago, Illinois 60614
    From
    $134
    / Night
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    1 / 11
    4.5 of 5 stars (8) Very good
    Near North Side
    1 Bedroom, 1 Bathroom, Sleeps 2
    Overview Reviews (8) Make Inquiry
    Overview Reviews (8)
    Amenities & Details
    • DVD Player
    • Hot Tub
    • Washer
    • Internet Access
    • Shared Outdoor Pool...
    • Satellite TV
    • Stereo System
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    1 bedroom fully furnished apartment in the heart of Gold Coast/River North, walking distance to transportation, restaurants and the lake front. The apartment comes fully furnished, has equipped kitchen, flat screen TVs, basic cable, Internet, phone and all utilities are included. The price also... View all property information
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    Location Information
    Chicago, Illinois 60654
    From
    $315
    / Night
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    1 / 32
    5 of 5 stars (2) Excellent
    The Loop
    3 Bedrooms, 2 Bathrooms, Sleeps 6
    Overview Reviews (2) Make Inquiry
    Overview Reviews (2)
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Take me to the Penthouse! Stay in our Penthouse Condo on the 50th Floor! A true Penthouse, stunning views of the lake and city. Walk to everything downtown. Upgraded everything. Granite kitchen counter tops, stainless steal appliances, marble in the bathrooms, king size beds, floor to ceiling... View all property information
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    Location Information
    Chicago, Illinois 60606
    From
    $315
    / Night
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    1 / 12
    4 of 5 stars (11) Very good
    The Loop
    3 Bedrooms, 2 Bathrooms, Sleeps 6
    Overview Reviews (11) Make Inquiry
    Overview Reviews (11)
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Walk to Everything Downtown! Enjoy Stunning Views of the City Skyline and Grant Park! ONE OF FEW 3BD/2.5BA UNITS RIGHT IN THE MIDDLE OF DOWNTOWN CHICAGO. Very affordable! ***WALK TO EVERYTHING ***YES, THESE ARE THE VIEWS! ***BREATHTAKING VIEWS OF THE CITY SKYLINE AND GRANT PARK ***3... View all property information
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    Location Information
    Chicago, Illinois 60601
    From
    $190
    / Night
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    1 / 9
    Gold Coast, Near North Side
    1 Bedroom, 1 Bathroom, Sleeps 3
    Overview Make Inquiry
    Overview
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    • Elevator/Lift access
    • Washer
    • Satellite TV
    • Air Conditioning
    • Gym
    • Shared Outdoor Pool...
    • DVD Player
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Streeter Place is a remarkable new building designed for those who enjoy the very best that Chicago has to offer. From its progressive architecture to its distinctive lobby décor, Streeter Place offers a unique concept in urban living. Located in trendy Streeterville, Streeter Place is the smart... View all property information
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    Location Information
    Chicago, Illinois 60611
    From
    $190
    / Night
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    1 / 10
    The Loop
    1 Bedroom, 1 Bathroom, Sleeps 3
    Overview Make Inquiry
    Overview
    Amenities & Details
    • Washer
    • TV
    • Elevator/Lift access
    • Shared Outdoor Pool...
    • Wi-Fi
    • Air Conditioning
    • DVD Player
    • Housekeeping...
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Chicago’s newest addition to Lakeshore East, Coast creates a coastal retreat on the shores of Lake Michigan. This beautiful property is situated in Chicago’s most desirable location with magnificent views of the River, the Lake and the world famous Chicago Skyline. View all property information
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    Location Information
    Chicago, Illinois 60601
    From
    $300
    / Night
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    1 / 11
    4 of 5 stars (3) Very good
    Roscoe Village
    3 Bedrooms, 2 Bathrooms, Sleeps 8
    Overview Reviews (3) Make Inquiry
    Overview Reviews (3)
    Amenities & Details
    • Towels Provided
    • Soap/Shampoo...
    • Air Conditioning
    • Internet Access
    • Linens Provided
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Trendy Roscoe Village offers a variety of boutiques, restaurants and bars. Our Guesthouse is located a block from 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,... View all property information
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    Location Information
    Chicago, Illinois 60618
    From
    $250
    / Night
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    1 / 11
    4.5 of 5 stars (3) Very good
    Roscoe Village
    2 Bedrooms, 2 Bathrooms, Sleeps 6
    Overview Reviews (3) Make Inquiry
    Overview Reviews (3)
    Amenities & Details
    • Outdoor Dining Area
    • Air Conditioning
    • Soap/Shampoo...
    • Towels Provided
    • Internet Access
    • Linens Provided
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Trendy Roscoe Village offers a variety of boutiques, restaurants and bars. Our Guesthouse is located above Cinnamon Boutique, a new women's clothing and accessory store and one of many fantastic places to shop in the village. We are approximately 4.5 blocks from the Paulina brown stop, which will... View all property information
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    Location Information
    Chicago, Illinois 60618
    From
    $225
    / Night
    View Details
    1 / 8
    Roscoe Village
    2 Bedrooms, 2 Bathrooms, Sleeps 6
    Overview Make Inquiry
    Overview
    Amenities & Details
    • Grill
    • Fireplace
    • Towels Provided
    • Stove
    • Refrigerator
    • Linens Provided
    • Dishwasher
    • Garage
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Located in the Heart of Roscoe Village--'A village within the city.' Trendy Roscoe Village offers a variety of boutiques, restaurants and bars. We are approximately 7 blocks from the Paulina brown stop, which will take you downtown in approximately 15 minutes. We are also located a short... View all property information
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    Location Information
    Chicago, Illinois 60618
    From
    $260
    / Night
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    1 / 12
    4 of 5 stars (2) Very good
    Near North Side
    2 Bedrooms, 2 Bathrooms, Sleeps 4
    Overview Reviews (2) Make Inquiry
    Overview Reviews (2)
    Amenities & Details
    • Gym
    • Air Conditioning
    • Internet Access
    • DVD Player
    • Water Views
    • Stereo System
    • Shared Outdoor Pool...
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    2 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
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    Location Information
    Chicago, Illinois 60654
    From
    $275
    / Night
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    1 / 4
    Roscoe Village
    4 Bedrooms, 2 Bathrooms, Sleeps 10
    Overview Make Inquiry
    Overview
    Amenities & Details
    • Soap/Shampoo...
    • Towels Provided
    • Linens Provided
    • Fireplace
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Brand new 4 bedroom 2 bath fully furnished apartment in Roscoe Village close to Hamlin Park. Whether you are planning a weekend excursion, business trip or need a comfortable place to stay for family or friends, consider our newly rehabbed Guesthouse on Leavitt St. We do allow 1-2 nights stays... View all property information
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    Location Information
    Chicago, Illinois 60618
    From
    $250
    / Night
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    1 / 10
    4.5 of 5 stars (6) Very good
    The Loop
    2 Bedrooms, 2 Bathrooms, Sleeps 6
    Overview Reviews (6) Make Inquiry
    Overview Reviews (6)
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    **LOCATION **LOCATION **LOCATION! ***CAN'T BEAT IT! ***Views Views Views! Breathtaking Lake and City Views!!*** Looks Like Hawaii Up There!*** Set in the heart of Downtown Chicago, our Chicago apt is ideally placed for visitors to experience all that the city has to offer. On the doorstep of... View all property information
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    Location Information
    Chicago, Illinois 60605
    From
    $105
    / Night
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    1 / 7
    3.5 of 5 stars (7) Average
    Near North Side
    1 Bedroom, 1 Bathroom, Sleeps 4
    Overview Reviews (7) Make Inquiry
    Overview Reviews (7)
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    Excellent Location: 1 block to the Navy Pier and lakefront 2 blocks to the shopping area on Michigan Ave Just on the other side of the river from Grant Park and Millennium Park (15 min walk) Large Unit: Largest 1bd/1ba floor plan downtown Wrap around windows, corner unit Full size kitchen,... View all property information
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    Location Information
    Chicago, Illinois 60611
    From
    $145
    / Night
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    1 / 7
    5 of 5 stars (1) Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 4
    Overview Reviews (1) Make Inquiry
    Overview Reviews (1)
    Amenities & Details
    • Hot Tub
    • Stereo System
    • Fireplace
    • Satellite TV
    • Air Conditioning
    • Sauna
    • Internet Access
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    If you're looking for a quiet and quaint stay in Chicago that is minutes away from all of the downtown action, then the Casa in 'Little Italy' is the vacation rental you've been looking for. The Casa will provide you with a taste of the lifestyle that most 'Normal' people call life in the City of... View all property information
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    Location Information
    Chicago, Illinois 60607
    From
    $179
    / Night
    View Details
    1 / 6
    Near North Side
    1 Bedroom, 1 Bathroom, Sleeps 4
    Overview Make Inquiry
    Overview
    Amenities & Details
    • Satellite TV
    • Dryer
    • Air Conditioning
    • Stove
    • Linens Provided
    • Refrigerator
    • Patio
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Homewood Suite by Hilton Chicago Downtown/Magnificent Mile. The spacious suite at this Magnificent Mile is ideal for extended-stay guests or families and feature full kitchens with refrigerators, microwaves, two-burner cooktops and dishwashers. Upgrade to a specialty suite on the 39th floor for... View all property information
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    Location Information
    Chicago, Illinois 60611
    From
    $133
    / Night
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    1 / 7
    The Loop
    2 Bedrooms, 2 Bathrooms, Sleeps 4
    Overview Make Inquiry
    Overview
    Amenities & Details
    • Water Views
    • DVD Player
    • Garage
    • Air Conditioning
    • Washer
    • Dryer
    • Satellite TV
    • Hot Tub
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    , overlooking city, Lake Michigan and the Chicago River. Fully furnished 2 bedroom/2 bath. Building amenities include work-out room, swimming pool, hot tub, parking, dry cleaners on-site, food market on-site. Beds: 1 Queen Bed, 1 Double Bed View all property information
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    Location Information
    Chicago, Illinois 60601
    From
    $100
    / Night
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    1 / 10
    4 of 5 stars (1) Very good
    Gold Coast, Near North Side
    1 Bedroom, 1 Bathroom, Sleeps 3
    Overview Reviews (1) Make Inquiry
    Overview Reviews (1)
    Amenities & Details
    • Dryer
    • Hot Tub
    • Water Views
    • Deck
    • Internet Access
    • Satellite TV
    • Air Conditioning
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Located in the heart of Chicago, these Corporate Furnished Apartments offer breathtaking views, rooftop deck with poolside service, premier gym, wireless internet lounge, and much more. Overlooking 1,200 acres of glorious Lincoln Park greenery and offering panoramic views of Lake Michigan, our... View all property information
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    Location Information
    Chicago, Illinois 60610
    From
    $400
    / Night
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    1 / 7
    The Loop
    3 Bedrooms, 2 Bathrooms, Sleeps 6
    Overview Make Inquiry
    Overview
    Amenities & Details
    • Satellite TV
    • Hot Tub
    • Air Conditioning
    • Internet Access
    • Waterfront
    • Water Views
    • Deck
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Beautifully done high-end furnished 3 bedroom | 2 bath | located downtown Chicago Beds: 1 King Bed, 2 Queen Beds View all property information
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    Location Information
    Chicago, Illinois 60616
    From
    $200
    / Night
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    1 / 37
    Near North Side
    2 Bedrooms, 2 Bathrooms, Sleeps 6
    Overview Make Inquiry
    Overview
    Amenities & Details
    • Satellite TV
    • Stereo System
    • Water Views
    • Refrigerator
    • Balcony
    • Air Conditioning
    • DVD Player
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    **LOCATION **LOCATION **LOCATION! ***CAN'T BEAT IT! ***Views Views Views! Breathtaking Lake and City Views!!*** Looks Like Hawii Up There!*** Set in the heart of Downtown Chicago, our Chicago apt is ideally placed for visitors to experience all that the city has to offer. On the doorstep of... View all property information
    Make Inquiry
    Location Information
    Chicago, Illinois 60611
    From
    $169
    / Night
    View Details
    1 / 6
    The Loop
    1 Bedroom, 1 Bathroom, Sleeps 4
    Overview Make Inquiry
    Overview
    Amenities & Details
    • Internet Access
    • Air Conditioning
    • Linens Provided
    • Hairdryer
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Hard Rock Hotel Chicago Enjoy downtown Chicago for work and play! Rock and relaxation take center stage at Hard Rock Tune into the good vibrations and relax in a world-famous cityscape at Hard Rock Hotel Chicago. Our hotel, housed in the historic Carbide & Carbon skyscraper, provides the... View all property information
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    Location Information
    Chicago, Illinois 60601
    From
    $500
    / Night
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    1 / 17
    DePaul
    4 Bedrooms, 4 Bathrooms, Sleeps 24
    Overview Make Inquiry
    Overview
    Amenities & Details
    • Deck
    • Stereo System
    • Washer
    • Air Conditioning
    • Fireplace
    • DVD Player
    • Internet Access
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Vacation in the best neighborhood in Chicago in this amazing Furnished Custom Single Family Home. This home is 15 blocks from Wrigley Field, 5 blocks to the Kennedy Expressway, 6 blocks to the EL, 2 blocks to grocery stores, etc, etc. Everything you need is here! This is a top of the line... View all property information
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    Location Information
    Chicago, Illinois 60614
    From
    $495
    / Night
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    1 / 30
    Lakeview
    6 Bedrooms, 2 Bathrooms, Sleeps 16
    Overview Make Inquiry
    Overview
    Amenities & Details
    • Dryer
    • Air Conditioning
    • Washer
    • Patio
    • Deck
    • Internet Access
    • Stereo System
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Chicago Vacation Rental lenience # 2320200 This well kept property sleeps up to 16 comfortably. Enjoy the nice Wrigley Located property with great outdoor space and a sunny interior. Additional bonus includes a a huge patio/ lounge with grill and garden and a two car garage. Between the... View all property information
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    Location Information
    Chicago, Illinois 60613
    From
    $200
    / Night
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    1 / 5
    3 of 5 stars (1) Average
    The Loop
    2 Bedrooms, 1 Bathroom, Sleeps 5
    Overview Reviews (1) Make Inquiry
    Overview Reviews (1)
    Amenities & Details
    • Stereo System
    • Washer
    • Fireplace
    • Dryer
    • Internet Access
    • Satellite TV
    • Air Conditioning
    • Hot Tub
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    This lovely 2 Bedroom sits in the Downtown/Gold Coast area. Voted in the top 5 areas that are 'walkable' No need for a car to see this lovely city! Although, there is a parking place provided if needed at no extra cost! Fully upgraded unit, with a fireplace, and balcony for your enjoyment. State of... View all property information
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    Location Information
    Chicago, Illinois
    From
    $169
    / Night
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    1 / 6
    The Loop
    Studio, 1 Bathroom, Sleeps 4
    Overview Make Inquiry
    Overview
    Amenities & Details
    • Air Conditioning
    • Internet Access
    • Hairdryer
    • Stereo System
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Wyndham Grand Chicago River With sweeping views of the city skyline and Chicago River and plush oversized studio, the Wyndham Grand Chicago Riverfront provides the ideal home base for exploring our great city. This accommodation is outfitted with the latest modern amenities like complimentary... View all property information
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    Location Information
    Chicago, Illinois 60601
    From
    $189
    / Night
    View Details
    1 / 8
    The Loop
    Studio, 1 Bathroom, Sleeps 4
    Overview Make Inquiry
    Overview
    Amenities & Details
    • Microwave
    • Air Conditioning
    • Linens Provided
    • Internet Access
    • Refrigerator
    • Satellite TV
    • Parking
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    At Comfort Suite, we offer you a apartment designed to meet the needs of a relaxing vacation. Book with our Chicago studio; our great rates and friendly staff will help make your next trip more affordable and enjoyable.Get going with a great breakfast. Start your trip to Chicago with our free hot... View all property information
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    Location Information
    Chicago, Illinois 60601
    From
    $800
    / Night
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    1 / 17
    Northwest Side
    4 Bedrooms, 3 Bathrooms, Sleeps 20
    Overview Make Inquiry
    Overview
    Amenities & Details
    • Patio
    • Satellite TV
    • Stereo System
    • Air Conditioning
    • Grill
    • Fireplace
    • Internet Access
    • Deck
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • ?
    About this property
    Gorgeous, huge, sun filled loft for a maximum of 12 guests. Very unique with antique skylights, timber ceiling, gourmet kitchen, and grand fireplace. We have 2 king beds, 1 full bed, and plenty of space for additional air mattresses. We have 2 full baths, and 1 half bath. Guests are conveniently... View all property information
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    Location Information
    Chicago, Illinois 60647