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Weekend Getaways in Chicago - Vacation Rentals

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    All 181 Rentals in Chicago
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    From
    $400
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    1 / 7
    The Loop
    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    $1,277
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    1 / 49
    Lakeview
    11 Bedrooms / 6 Bathrooms / Sleeps 21
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    $695
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    1 / 26
    Lakeview
    6 Bedrooms / 2 Bathrooms / Sleeps 16
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    $499
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    1 / 31
    Lakeview
    5 Bedrooms / 2 Bathrooms / Sleeps 9
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    About this property
    Beautiful & Spacious! Vintage Charm 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; undeniably charming. Glance around and you’ll see large, colorful... View all property information
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    Location Information
    Chicago, Illinois 60613
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    $838
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    1 / 37
    Lakeview
    6 Bedrooms / 3 Bathrooms / Sleeps 14
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    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
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    $300
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    1 / 6
    Roscoe Village
    4 Bedrooms / 2 Bathrooms / Sleeps 8
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    About this property
    Brand new 4 bedroom 2 bath fully furnished apartment in the heart of Roscoe Village. Whether you’re planning a weekend excursion, business trip or need a comfortable place to stay for family or friends, consider our newly rehabbed Guesthouse on Roscoe St. Trendy Roscoe Village offers boutique... View all property information
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    Location Information
    Chicago, Illinois 60657
    From
    $105
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    1 / 4
    1 Bedroom / 1 Bathroom / Sleeps 4
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    About this property
    Welcome to Chicago! Come visit our 1bd/1ba condo. This is a very large unit -- the largest floor plan downtown. Our condo is located in the heart of downtown Chicago. It is 1 block from the Navy Pier where there are shops, restaurants and the lakefront. We are a 5 min walk to the Michigan... View all property information
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    Location Information
    Chicago, Illinois 13456
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    $500
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    1 / 17
    DePaul
    4 Bedrooms / 4 Bathrooms / Sleeps 24
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    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
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    $250
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    1 / 24
    Lakeview
    2 Bedrooms / 1 Bathroom / Sleeps 4
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    • Pets allowed
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    • ?
    • x
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    • Elder access
    • x
    About this property
    An irresistibly charming apartment! Good things do come in small packages! 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 homerecaptured; undeniably charming. Glance around... View all property information
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    Location Information
    Chicago, Illinois 60657
    From
    $459
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    1 / 13
    5 Bedrooms / 3 Bathrooms / Sleeps 11
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    • Satellite TV
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    • Pets allowed
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    • Suitable for children
    • x
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    About this property
    Enjoy this newly completed high-end renovation of a classic Brownstone home with 5 spacious bedrooms, 3 full baths and home theater equipped living rooms. This beautiful home is located on a quiet, tree lined street on the Northside of Chicago. Located in the Lincoln Square neighborhood, there are... View all property information
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    Location Information
    Chicago, Illinois 60625
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    From
    $149
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    1 / 17
    The Loop
    2 Bedrooms / 2 Bathrooms / Sleeps 5
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    • Satellite TV
    • Sauna
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    • Pets allowed
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    • Suitable for children
    • x
    • x
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    About this property
    Please call/e-mail for more information. Beds: 2 Queen Beds View all property information
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    Location Information
    Chicago, Illinois 60602
    From
    $109
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    1 / 9
    Northwest Side
    2 Bedrooms / 2 Bathrooms / Sleeps 5
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    • x
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    About this property
    This is a 2 bedroom, 2 bathrooms, vintage building that has been rehabbed. This Chicago vacation rental apartment is located on Kedzie Blvd in Chicago, near the blue line. The apartment has washer/dryer in unit, stainless steal appliance, granite counter tops, Beds: 2 Queen Beds View all property information
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    Location Information
    Chicago, Illinois 60647
    From
    $103
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    1 / 17
    Roscoe Village
    2 Bedrooms / 1 Bathroom / Sleeps 8
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    • Air Conditioning
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
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    • x
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    About this property
    Beautifully rehabbed with brand new eat-in kitchen and bath. Hardwood floors throughout apartment. All trim and woodwork has been magnificently restored to it's original look. Washer and dryer in unit Central air with individual controls for heat and AC. Guest love the huge outdoor finished space... View all property information
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    Location Information
    Chicago, Illinois 60618
    From
    $139
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    1 / 15
    The Loop
    Studio / 1 Bathroom / Sleeps 2
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    • Air Conditioning
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    • Waterfront
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    • Pets allowed
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    • x
    • x
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    • x
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    About this property
    Corporate furnished apartment in the heart of Millennium Park, walking distance to transportation, restaurants and the lake front. The apartment comes fully furnished, has equipped kitchen, flat screen TVs, basic cable, Internet and all utilities are included. Rates vary based on availability... View all property information
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    Location Information
    Chicago, Illinois
    From
    $315
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    1 / 5
    3 Bedrooms / 3 Bathrooms / Sleeps 6
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    • Pets allowed
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    • x
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    • x
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    About this property
    Professionally decorated, this air-conditioned, 3 bedroom condo can easily lodge up to 10 guests. All the 3 bedrooms include king-size bed. The bathroom is well appointed as per modern standards.If guests decide to prepare yummy meals at home , then they can enjoy cooking in well stocked kitchen... View all property information
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    Location Information
    Chicago, Illinois 13456
    From
    $175
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    1 / 35
    4 Bedrooms / 2 Bathrooms / Sleeps 8
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    • Air Conditioning
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
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    • x
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    About this property
    Large Rental In A Neighborhood That Has Kept Its Old World Charm With The New! Large, Cozy Place Ideal For Value Seekers Looking For A Memorable And Culturally-diverse Experience In A Quaint Neighborhood That's Also A Convenient Base To Explore Other Fun Sites In Chicago. From A Relatively... View all property information
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    Location Information
    Chicago, Illinois 60625
    From
    $110
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    1 / 8
    Northwest Side
    1 Bedroom / 1 Bathroom / Sleeps 4
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    • Air Conditioning
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    • Pets allowed
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    • x
    • x
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    • x
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    About this property
    Vintage Mansion on Kedzie Blvd - Vacation Rental License xxxxxx property. This apartment is located on the 3rd floor of a Historic Mansion, overlooking Kedzie Blvd. in the city of Chicago. The apartment is very spacious, approximately 1200 sq ft of space, large living room, dinning and... View all property information
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    Location Information
    Chicago, Illinois 60647
    From
    $90
    / Night
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    1 / 36
    2 Bedrooms / 1 Bathroom / Sleeps 6
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    • Air Conditioning
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    • Elder access
    • x
    • ?
    About this property
    Comfy Rental In A Neighborhood That Has Kept Its Old World Charm With The New! Artsy, Quiet And Comfortable Place Ideal For Value Seekers Looking For A Memorable And Culturally-Diverse Experience In A Quaint Neighborhood That's Also A Convenient Base To Explore Other Fun Sites In Chicago.... View all property information
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    Location Information
    Chicago, Illinois 60625
    From
    $270
    / Night
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    1 / 4
    The Loop
    1 Bedroom / 1 Bathroom / Sleeps 4
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    • Internet Access
    • Satellite TV
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    • Elder access
    • x
    • ?
    About this property
    Experience the vibrancy of down town Chicago and delight in the modern, sleek comfort of wyndham grand Chicago river front — an intimate haven on the magnificent mile — offering chic accommodations in an exceptional setting. Just outside your door is Chicago's premier shopping avenue with over 450... View all property information
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    Location Information
    Chicago, Illinois 60601
    From
    $425
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    1 / 18
    2 Bedrooms / 2 Bathrooms / Sleeps 4
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    • Balcony
    • Waterfront
    • Water Views
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    Fully furnished two bedrooms, two baths. 'BEAUTIFUL' sun-rise and moon-rise on Lake Michigan from the living room and balcony. Laundry room in the building. Biking/walking trail and Lake Michigan is right across the street. No grocery stores, shops or restaurants in walking distance, only public... View all property information
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    Location Information
    Chicago, Illinois 60649
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    From
    $129
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    1 / 24
    Northwest Side, Wicker Park / Bucktown
    1 Bedroom / 1 Bathroom / Sleeps 2
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    • Air Conditioning
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    • Elder access
    • x
    • x
    About this property
    Near restaurants, cafés & bars in vibrant Wicker Park, this tucked away, free standing, 1 bedroom Coach House could be your Chicago oasis! The space includes, an outfitted kitchen as well as a private bathroom, deck & entrance. Located off a quiet tree-lined street near 19th century mansions built... View all property information
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    Location Information
    Chicago, Illinois 60622
    From
    $210
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    1 / 12
    3 Bedrooms / 2 Bathrooms / Sleeps 8
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
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    • Satellite TV
    • Washer
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
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    • Elder access
    • x
    • x
    About this property
    You won't find a better location than this bright and comfortable vacation rental, which is perfectly maintained to accommodate your needs away from home. The cta train is close and walking distance, and the bus stop is steps to the corner. You are also in walking distance of McKinley park,... View all property information
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    Location Information
    Chicago, Illinois 60609
    From
    $854
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    1 / 11
    The Loop
    1 Bedroom / 1 Bathroom / Sleeps 4
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    • Air Conditioning
    • Dishwasher
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    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • Wheelchair access
    • Elder access
    • ?
    About this property
    Enjoy stunning city views from your apartment and walk to work from this centrally located West Loop apartment. In your free time enjoy Michigan Avenue for shopping, as well as museums, restaurants and nightlife at your doorstep. The train, taxis, and buses are all accessible on the same block for... View all property information
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    Location Information
    Chicago, Illinois 60661
    From
    $249
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    1 / 10
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Gym
    • Internet Access
    • Washer
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
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    About this property
    Our suite features Two Bedrooms/Two Bathrooms with a pull out couch and can accommodate six guests. Suite also contains fully equipped gourmet kitchen and is perfect for families or individuals, traveling for business or pleasure. The Guesthouse Hotel offers great style, comfort and value. Stay... View all property information
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    Location Information
    Chicago, Illinois 60640
    From
    $800
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    1 / 17
    The Loop
    3 Bedrooms / 3 Bathrooms / Sleeps 12
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    • Air Conditioning
    • Dishwasher
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    • Fireplace
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    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
    From
    $300
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    1 / 11
    2 Bedrooms / 1 Bathroom / Sleeps 5
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Washer
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • x
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    • Elder access
    • x
    • x
    About this property
    Gorgeous 2 bedroom/1 bath located on the second floor of a classic Chicago 3-flat. Building is located in the heart of Lakeview, steps to the cta (no train noise), and walking distance to Wrigley Field and the Lake. Building had a full renovation in 2014 including a brand new kitchen with gorgeous... View all property information
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    Location Information
    Chicago, Illinois 60657
    From
    $130
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    1 / 6
    2 Bedrooms / 2 Bathrooms / Sleeps 1
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    • Air Conditioning
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    • Washer
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    • Pets allowed
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    • x
    • x
    • x
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    • Elder access
    • x
    About this property
    Cozy private bedroom and bathroom in a 2 bedroom apartment in Chicago's prime gold coast/ old town area. 5 blocks from Michigan Ave, Chicago's main shopping area, 3 blocks from Rush street and bar district. Old town is one of Chicago's best neighborhoods with some of the best restaurants and bars.... View all property information
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    Location Information
    Chicago, Illinois 60610
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    $279
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    1 / 24
    The Loop
    1 Bedroom / 2 Bathrooms / Sleeps 4
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    • Balcony
    • Dryer
    • Hot Tub
    • Internet Access
    • Ocean Views
    • Pool Table
    • Sauna
    • Shared Indoor Pool
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
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    • Elder access
    • x
    About this property
    Enjoy this 36th floor studio in one of the most modern and luxurious skyscrapers in Chicago, The Aqua. The unit is 720 sq ft studio (as large as a 1 bedroom, but with a partial wall separating the living space from bedroom). Granite counter tops, stainless steel appliances, 42 inch flat screen TV... View all property information
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    Location Information
    Chicago, Illinois 60601
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    $300
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    1 / 23
    2 Bedrooms / 1 Bathroom / Sleeps 6
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Internet Access
    • Private Outdoor...
    • Satellite TV
    • Washer
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • x
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    • Elder access
    • x
    • x
    About this property
    The South Loop is classic Chicago. In the South Loop, streets with decades of history come alive as music and life pulse magnetically. Chicago's South Loop is a neighborhood that's buzzing with bars, restaurants and entertainment; it's the perfect place to stay during your time in Chicago. The... View all property information
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    Location Information
    Chicago, Illinois 60616
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    $133
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    1 / 7
    The Loop
    2 Bedrooms / 2 Bathrooms / Sleeps 4
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    • Air Conditioning
    • Dishwasher
    • Dryer
    • Hot Tub
    • Satellite TV
    • Washer
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • 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
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    $129
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    1 / 43
    Lakeview
    1 Bedroom / 1 Bathroom / Sleeps 4
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    • Air Conditioning
    • Internet Access
    • Satellite TV
    • Wi-Fi
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
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    About this property
    Located in Chicago's East Lakeview Neighborhood (home of Wrigleyville and Boystown), our Junior 1-Bedroom Apartment provides peace & quiet while only minutes away from Chicago's best attractions. Steps from Lake Michigan and Belmont Harbor; with easy access to the lakefront, nightlife, dining,... View all property information
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    Location Information
    Chicago, Illinois 60657