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Apartment Rentals and Condos in Chicago, IL

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    Travelers to Chicago are booking May dates now. Secure your vacation rental today, and have the perfect trip.
    1 / 4
    The Loop
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    1 / 14
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    1 / 49
    Lakeview
    11 Bedrooms, 6 Bathrooms, Sleeps 21 | Quick View
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    1 / 24
    Northwest Side, Wicker Park / Bucktown
    5 Bedrooms, 3 Bathrooms, Sleeps 14 | Quick View
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    $217
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    • Grill
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    • x
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    About this property
    Beautiful Brick Single Family Rowhome in convenient Bucktown location. Bright and open family friendly layout great for entertaining. Large eat-in kitchen with deck access. Master suite w/ private outdoor deck. 2 other large bedrooms on this level. Basement/Lower level has 2 additional bedrooms as... View all property information
    Location Information
    Chicago, Illinois 60647
    1 / 6
    Roscoe Village
    4 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    $213
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    • x
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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
    Location Information
    Chicago, Illinois 60657
    1 / 17
    DePaul
    4 Bedrooms, 4 Bathrooms, Sleeps 24 | Quick View
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    $500
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    • x
    • x
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    About this property
    Vacation in the best neighborhood in Chicago in this amazing Furnished Custom Single Family Home which is fully licensed by the City #2262746! Don't trust places which don't have a license! This home is 15 blocks from Wrigley Field, 5 blocks to the Kennedy Expressway, 6 blocks to the EL, 2... View all property information
    Location Information
    Chicago, Illinois 60614
    1 / 18
    4 of 5 stars (2) Very good
    3 Bedrooms, 1 Bathroom, Sleeps 9 | Quick View
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    $139
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    • Parking
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    • Private Yard
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    • ?
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    • x
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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
    5 of 5 stars Reviewed July 18, 2014
    Nice location. Everyone got their own beds. Easy to downtown. Kitchen and free laundry. Free Tide detergent too (not expected). Will stay again.
    3 of 5 stars Reviewed May 7, 2014
    The location of this property was great. It was about 12-15 minutes from downtown, which is where we wanted to be. There was plenty of on-street parking right in front of the...
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    Roscoe Village
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    $249
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    • DVD Player
    • Porch
    • Outdoor Dining Area
    • Washer
    • Air Conditioning
    • Grill
    • Internet Access
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
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    • Elder access
    • x
    About this property
    Welcome to your home away from home nestled in the Village within the City – Roscoe Village in Chicago, IL. Roscoe Village is a very family friendly neighborhood. This warm and welcoming first floor unit features a high end kitchen equipped with stainless appliances & granite countertops, 1 King... View all property information
    Location Information
    Chicago, Illinois 60618
    Lincoln Square
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    $190
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    About this property
    The Space Beautiful 2 Floor Duplexapartment near Foster and Damen on the North Side of Chicago. •3 bedrooms 2 Full Bathrooms •Full modern kitchen •Wireless internet •Cable with Smart TV have access to your Netflix and Hulu Accounts • Large Outdoor Deck w/ BBQ •Laundry in Unit The apartment... View all property information
    Location Information
    Chicago, Illinois 60625
    1 / 38
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    $90
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    • Satellite TV
    • DVD Player
    • Internet Access
    • Parking
    • Air Conditioning
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    • x
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    • Smoking allowed
    • Elder access
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    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
    Location Information
    Chicago, Illinois 60625
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    1 / 51
    2 of 5 stars (1) Poor
    Near North Side
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    $192
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    • Satellite TV
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    • Washer
    • Terrace
    • Balcony
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
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    • x
    • ?
    About this property
    Included is a 3-bedroom fully furnished “Old Town Chicago” condo with TWO PRIVATE BALCONIES, Flat Panel HDTVs, Fireplaces, All Utilities, All Major Appliances, WiFi, Internet, Cable, Queen Size Mattresses, Cleaning Service upon Vacating Included, Complimentary Laundry, and all of the atmosphere... View all property information
    Location Information
    Chicago, Illinois 60610
    1 / 21
    5 of 5 stars (1) Excellent
    Northwest Side
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    $175
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    • Parking
    • Wi-Fi
    • Porch
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    • Patio
    • DVD Player
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    • Smoking allowed
    • Elder access
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    About this property
    Our 3 bedroom cozy house feels like a cottage in the middle of the popular Avondale Neighborhood. It's perfect place for a family up to 8, we are a block from a park, Target and the river. Enjoy restaurants and a craft brewery all within in 3 blocks. Entire house with 2 bedrooms and bath... View all property information
    Location Information
    Chicago, Illinois 60618
    5 of 5 stars Reviewed October 3, 2015
    This 4 bedroom 2 full bath was very clean, well stocked, in a good neighborhood, had a very nice park for our grand children to play at within a block, great restaurants within...
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    1 / 40
    5 of 5 stars (1) Excellent
    Lakeview
    6 Bedrooms, 3 Bathrooms, Sleeps 14 | Quick View
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    $536
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    • Washer
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    • Balcony
    • Porch
    • Waterfront
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
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    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Chicago Guest House is the absolute BEST choice for business & leisure travelers who want to experience the sense of having arrived 'home' while they are in Chicago! A Vintage Beauty With All the Modern Comforts & Amenities. Beautifully furnished and fully equipped--guaranteed a unique and... View all property information
    Location Information
    Chicago, Illinois 60657
    5 of 5 stars Reviewed September 11, 2015
    Teri's Guest House at Newport is a wonderful home away from home for any type of traveler. Family getaway, girls/boys weekend, or a date weekend, this location and apartment meets...
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    3 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    $225
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
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    • Smoking allowed
    • Elder access
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    • x
    About this property
    Great short-term furnished rental option in Chicago. Condo-quality home is bright, clean, and well-maintained by diligent owner. Home is on one of Lincoln Square's most sought after side streets. New white eat-in kitchen with river white granite, stainless steel appliances, integrated dishwasher,... View all property information
    Location Information
    Chicago, Illinois 60625
    1 / 37
    The Loop
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
    From
    $3,600
    / Month
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    • Washer
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    • Pet-friendly
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    • Child-friendly
    • ?
    • ?
    • ?
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    • Elder access
    • ?
    • ?
    About this property
    Huge beautiful 1 bedroom with loads of space and all furnishings you need. This unit features beautiful wall to wall hardwood floors and upgraded carpeting in bedroom, stunning updated kitchen with quartz countertops and espresso cabinetry, large marble bathrooms, floor to ceiling windows with... View all property information
    Location Information
    Chicago, Illinois 60601
    Hyde Park
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    $75
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    • x
    • x
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    • Elder access
    • x
    • x
    About this property
    Our brand new master suite's high ceilings, Juliet balcony and modern, yet rustic finishes, will leave you feeling refreshed. Just steps away from the U of C,, our place fits two and is perfect for future students and families looking to be nearby! This private bedroom and bath are located on the... View all property information
    Location Information
    Chicago, Illinois 606155114
    1 / 21
    Near North Side
    4 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
    From
    $499
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    • DVD Player
    • Grill
    • Washer
    • Air Conditioning
    • Satellite TV
    • Balcony
    • Patio
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    This unit is located on two floors. Ideal for families and groups traveling together and also traveling with nanny's. Two Kitchens, One Larger kitchen fully equipped and brand new also a wet bar for entertaining and walk out balcony with seating. This property is 4600 SF and boasts gorgeous high... View all property information
    Location Information
    Chicago, Illinois 60654
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    $189
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    • Air Conditioning
    • Satellite TV
    • DVD Player
    • Wi-Fi
    • Terrace
    • Washer
    • Grill
    • Balcony
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    3 bedrooms, 2 full bathrooms, Balcony with Grill, sleeps 8. Kid Friendly Live like a local in one of Chicago's best neighborhoods at a top-rated TripAdvisor property! Located in a family-owned boutique building in the vibrant and historic Andersonville neighborhood, our Chicago vacation property... View all property information
    Location Information
    Chicago, Illinois 60640
    1 / 20
    4.5 of 5 stars (17) Very good
    West Town
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    $110
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    • Pet-friendly
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    • x
    • x
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    • 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
    Location Information
    Chicago, Illinois 60642
    4 of 5 stars Reviewed May 25, 2015
    I came here for 5 days with a group of 7 (3 were couples, 1 was solo) This was place is a steal! it was wayyy bigger than we expected, we were all very comfortable, had our...
    5 of 5 stars Reviewed March 18, 2015
    The owners are super nice and answered all of my questions within a couple of days. The apartment has a lot of space to it. Three bathrooms makes it very comfortable. Two beds...
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    Northwest Side
    2 Bedrooms, 2 Bathrooms, Sleeps 12 | Quick View
    From
    $299
    / Night
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    • Outdoor Dining Area
    • Porch
    • DVD Player
    • Air Conditioning
    • Grill
    • Wi-Fi
    • Washer
    • Balcony
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    The space is fresh and open and can sleep 8 on individual beds and 12 if you double up on the queen mattresses. There are 2 sets of bunk beds in a small 3rd bedroom/bonus room. There are 2 living rooms which makes it easy to get away from your mates when one wants to have some quiet time or giving... View all property information
    Location Information
    Chicago, Illinois 60622
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    1 / 15
    4.5 of 5 stars (4) Very good
    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    $80
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    • Washer
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    • Pet-friendly
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    • Child-friendly
    • x
    • x
    • x
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    • Elder access
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    About this property
    Furnished Studio. Double bed, full bath, and full kitchen. 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 public... View all property information
    Location Information
    Chicago, Illinois 60640
    3 of 5 stars Reviewed August 13, 2015
    Beautiful tree lined street close to down town express, lake front and bike hire. Great supermarket around 2 corners. Studio is in an older building that has seen better days. No...
    4 of 5 stars Reviewed September 3, 2014
    Great stay, close to the El train and cheaper than a hotel! Able to stay parked out front for free and take the El where ever we wanted to. If you want a great stuffed pizza...
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    1 / 30
    5 of 5 stars (1) Excellent
    Lakeview
    4 Bedrooms, 4 Bathrooms, Sleeps 14 | Quick View
    From
    $295
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    • Air Conditioning
    • Grill
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    License#2314739 This is a luxury property consistent of two units one above the other. Book one or both to accommodate the size of your group. A total of 4 bedroom 4 bath brand new construction luxury condos. We are a licensed vacation rental property with the City of Chicago... View all property information
    Location Information
    Chicago, Illinois 60613
    5 of 5 stars Reviewed May 26, 2015
    This rental was absolutely amazing. The owners were very easy to get a hold of & the place was very clean, updated, and accommodated our group of 13 perfectly. The location was...
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    other travelers have booked this property
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    $139
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    • Secure Parking
    • Air Conditioning
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    • Balcony
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    • Grill
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Our suite features Two Bedrooms/Two Bathrooms with a pull out couch and can accommodate six guests. Suite also contains fully equipped gourmet kitchen and is perfect for families or individuals, traveling for business or pleasure. The Guesthouse Hotel offers great style, comfort and value. Stay... View all property information
    Location Information
    Chicago, Illinois 60640
    1 / 9
    Near North Side
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
    From
    $130
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    • Washer
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    • DVD Player
    • Satellite TV
    • Internet Access
    • Shared Outdoor Pool...
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
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    • 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
    Location Information
    Chicago, Illinois 60611
    1 / 29
    Near North Side
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    $3,000
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    • Shared Outdoor Pool...
    • Internet Access
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
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    About this property
    Beautifully updated studio unit features a large open layout with loads of closet space. Unit features wall to wall dark hardwood floors, updated upgraded kitchen with espresso cabinetry and beautiful granite countertops, large windows exposing beautiful skyline views, huge closet space, and w/d in... View all property information
    Location Information
    Chicago, Illinois 60654
    1 / 40
    4.5 of 5 stars (8) Very good
    The Loop
    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    $60
    / Night
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    • Grill
    • Wi-Fi
    • Patio
    • DVD Player
    • Secure Parking
    • Satellite TV
    • Washer
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • Smoking allowed
    • Elder access
    • x
    About this property
    These high-end apartments have granite countertops, stainless steel appliances, cherry cabinets, washer/dryer in-unit, king beds, and a flat screen TV. One Bedroom Apartments have queen pull-out sofa beds. Enjoy all-inclusive pricing and automatic monthly credit card payment. All of our... View all property information
    Location Information
    Chicago, Illinois 60661
    5 of 5 stars Reviewed September 9, 2015
    Since this time my client was in downtown, I preferred a stay close by and hence they booked me in this apartment for my three week stay. When I reached the apartments after a...
    5 of 5 stars Reviewed July 23, 2015
    In January 2015 I found out that I needed to get a rental in town for 5 weeks due to a summer program at Joffrey Ballet n which my daughter would be participating. I needed a...
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    1 / 23
    5 of 5 stars (1) Excellent
    Northwest Side
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    From
    $300
    / Night
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    • Satellite TV
    • Washer
    • Patio
    • Grill
    • DVD Player
    • Air Conditioning
    • Parking
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
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    • Smoking allowed
    • Elder access
    • x
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    About this property
    Gorgeous, Luxury Oak Park area Townhome…corner unit…completely furnished….close proximity (2 min.) to the historic Oak Park area…home of Frank Lloyd Wright and Ernest Hemingway! Beautiful landscaping, total 2,000 sq. ft. , alarm system, central air. Stunning designer furnishings in every... View all property information
    Location Information
    Chicago, Illinois 60707
    5 of 5 stars Reviewed October 24, 2014
    We recently stayed at this property for a ladies weekend in the Chicago area. There were 6 of us and the townhouse was just the perfect choice for us. We had plenty of room and...
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    1 / 16
    4 of 5 stars (10) Very good
    DePaul
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
    other travelers have booked this property
    From
    $99
    / Night
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    • Internet Access
    • Grill
    • Air Conditioning
    • Washer
    • DVD Player
    • Satellite TV
    • Outdoor Dining Area
    • Parking
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    BEFORE YOU BOOK PLEASE NOTE THERE IS A 4 NIGHT MINIMUM FROM MAY THROUGH OCTOBER, WITH A 5 NIGHT MINIMUM FOR HOLIDAY WEEKENDS AND SPECIAL EVENT WEEKENDS. PLEASE DO NOT AUTOBOOK FOR PERIODS SHORTER THAN WHAT IS REQUIRED AS THE BOOKING WILL NOT BE HONORED. PLEASE EMAIL OR CALL WITH ANY QUESTIONS.... View all property information
    Location Information
    Chicago, Illinois 60614
    5 of 5 stars Reviewed June 20, 2015
    This was a great unit. Nice, clean, well decorated. Close to train stop and grocery store. Great location, great unit. Would recommend to anyone!
    4 of 5 stars Reviewed May 18, 2014
    When we first got in there was a rib bone on the floor in plain view, guess they missed it cleaning. The rest of the place was fine, but that's a gross way to start. The...
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    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    $60
    / Night
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    • Grill
    • Air Conditioning
    • Wi-Fi
    • DVD Player
    • Patio
    • Satellite TV
    • Sauna
    • Washer
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Choose from Studio, Jr. One Bedroom, One Bedroom and upgraded One Bedroom + Den apartments. An on-site pool highlights this modern apartment in Chicago's theatre district. The property is 1,650 feet from iconic Willis Tower and just 10 minutes' walk from Millennium Park. Check out live shows at... View all property information
    Location Information
    Chicago, Illinois 60606
    1 / 25
    4 of 5 stars (1) Very good
    Lakeview
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    From
    $234
    / Night
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    • Wi-Fi
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    • DVD Player
    • Patio
    • Parking
    • Satellite TV
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Chicago Guest House is the absolute BEST choice for business & leisure travelers who want to experience the sense of having arrived 'home' while they are in Chicago! A Vintage Beauty With All the Modern Comforts & Amenities. Beautifully furnished and fully equipped--guaranteed a unique and... View all property information
    Location Information
    Chicago, Illinois 60613
    4 of 5 stars Reviewed August 9, 2015
    Our extended family of six had a great time in Chicago, thanks in large part to having Teri's Guesthouse as the base for the busy weekend of wedding events. We even had a...
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    1 / 15
    5 of 5 stars (2) Excellent
    Near North Side
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    From
    $650
    / Night
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    • Satellite TV
    • Air Conditioning
    • DVD Player
    • Parking
    • Sauna
    • Washer
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    A Chicago Premier Suites property with fantastic city views, located in the heart of River North neighborhood in one of Chicago’s premier high rise buildings. City of Chicago License #2179945 This 2 bedroom/2 bath unit is over 1300 SF and well decorated with luxury type amenities. Key features... View all property information
    Location Information
    Chicago, Illinois 60654
    5 of 5 stars Reviewed October 23, 2014
    We rented a unit on the 35th floor for a family visit of sisters and sister-in-law. The view was beautiful and we were happy as soon as we stepped inside! Everything was clean...
    5 of 5 stars Reviewed July 25, 2013
    We rented this apartment for 10 days and found it very comfortable in an excellent location. Red line station and supermarket just one block away. Chicago Premier Suites replied...
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    other traveler has booked this property
    From
    $139
    / Night
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    • Patio
    • Satellite TV
    • Air Conditioning
    • Secure Parking
    • Wi-Fi
    • Balcony
    • Grill
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    TWO-BEDROOM SUITES WITH BALCONY Open gourmet kitchen with stainless appliances Granite breakfast bar Bright and sunny living room with 10' ceilings Private balcony complete with gas grill and patio furniture King-sized bed in the master bedroom Spa-like bathroom with glass shower Two Bedroom... View all property information
    Location Information
    Chicago, Illinois 60640
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    other travelers have booked this property
    From
    $250
    / Night
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    • Air Conditioning
    • Hot Tub
    • Internet Access
    • Washer
    • Satellite TV
    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
    Location Information
    Chicago, Illinois 60618
    1 / 16
    4 of 5 stars (2) Very good
    Northwest Side
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
    other travelers have booked this property
    From
    $140
    / Night
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    • Parking
    • Patio
    • Outdoor Dining Area
    • DVD Player
    • Washer
    • Air Conditioning
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    We created this new construction apartment to fit our family as a second home. We live in Arkansas but are from Chicago with friends and family all here. When we visit it is perfect for our family of 5 with a crib, bunk bed, and queen bed. A twin blow up air mattress can be available upon... View all property information
    Location Information
    Chicago, Illinois 60646
    5 of 5 stars Reviewed June 23, 2015
    We absolutely loved this place and will stay again next time we're in Chicago. It was surprisingly close to the airport. The owners made sure the place was cleaned prior to our...
    3 of 5 stars Reviewed May 29, 2015
    Let me just say the owners were so very helpful. Though when booking I did not realize it was located in a house basement, I would have love to had known that. We might have...
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    The Loop
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    From
    $600
    / Night
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    • Satellite TV
    • Washer
    • Air Conditioning
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Live like a Chicago local in luxury - the perfect location to take in downtown Chicago! Great for McCormick Place meetings - 10 min away! Easy access to Soldier Field, Museum Campus, Grant Park, Magnificent Mile, and steps from the L! Enjoy the perfect home-base for exploring Chicago for you and 7... View all property information
    Location Information
    Chicago, Illinois 60605
    1 / 8
    Northwest Side
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
    From
    $110
    / Night
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    • Internet Access
    • Air Conditioning
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    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
    Location Information
    Chicago, Illinois 60647
    1 / 11
    4.5 of 5 stars (8) Very good
    Near North Side
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
    From
    $130
    / Night
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    Amenities & Details
    • DVD Player
    • Hot Tub
    • Balcony
    • Internet Access
    • Shared Outdoor Pool...
    • Satellite TV
    • Washer
    • 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
    Location Information
    Chicago, Illinois 60654
    3 of 5 stars Reviewed August 5, 2015
    This place was in a great location, right around the corner from Grand Station on the red line. There is a grocery store Jewel-Osco on the block and quite a few restaurants...
    5 of 5 stars Reviewed June 26, 2014
    My husband and I stayed in a 1 bedroom apartment on the 34th floor of the AMLI River North building for 3 weeks. We rented the unit through Manilow Suites, a short term corporate...
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    Near North Side
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
    other travelers have booked this property
    From
    $150
    / Night
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    The Space 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... View all property information
    Location Information
    Chicago, Illinois 60614
    1 / 29
    5 of 5 stars (1) Excellent
    Lakeview
    5 Bedrooms, 2 Bathrooms, Sleeps 9 | Quick View
    From
    $319
    / Night
    Payment Protection
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    Amenities & Details
    • Satellite TV
    • Grill
    • Washer
    • Wi-Fi
    • Balcony
    • Patio
    • Air Conditioning
    • Porch
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Chicago Guest House is the absolute BEST choice for business & leisure travelers who want to experience the sense of having arrived 'home' while they are in Chicago! Beautifully furnished and fully equipped--guaranteed a unique and unforgettable experience for you, your family and friends.... View all property information
    Location Information
    Chicago, Illinois 60613
    5 of 5 stars Reviewed December 23, 2015
    Stayed in this house for three nights and had family come in for Christmas get together. It was absolutely perfect. The home is very well maintained with all of the personal...
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    The Loop
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    From
    $500
    / Night
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    • Washer
    • Air Conditioning
    • Satellite TV
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Live like a Chicago local in luxury - the perfect location to take in downtown Chicago! Great for McCormick Place meetings - 10 min away! Easy access to Soldier Field, Museum Campus, Grant Park, Magnificent Mile, and steps from the L! Enjoy the perfect home-base for exploring Chicago for you and... View all property information
    Location Information
    Chicago, Illinois 60605
    1 / 14
    5 of 5 stars (5) Excellent
    DePaul
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
    other travelers have booked this property
    From
    $88
    / Night
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    • Washer
    • Internet Access
    • Grill
    • Outdoor Dining Area
    • Air Conditioning
    • Satellite TV
    • DVD Player
    • Parking
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    NOTE This calendar is updated weekly not daily. . Please also note that holiday weeks and special event weeks are at higher rates and require longer bookings. Please email to inquire. For over 20 years, this family-run building, Blarney's Brownstone, has been offering quality rentals. Located... View all property information
    Location Information
    Chicago, Illinois 60614
    4 of 5 stars Reviewed November 18, 2015
    we stayed at this garden apartment during my last visit to Chicago to attend a conference. The location could not be better, close to CTA and wholefood market. nice neighborhood...
    5 of 5 stars Reviewed July 18, 2012
    We first stayed at this holiday rental last summer when visting our son at Depaul university. The location of the rental is good for exploring the lincoln park area and an...
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    1 / 4
    The Loop
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
    From
    $2,950
    / Month
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    • Internet Access
    • Shared Indoor Pool
    • Washer
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    A truly beautiful space that features a defined living area and bedroom space. Unit features wall to wall espresso hardwood floors, stunning kitchen with quartz countertops and snaidero cabinetry, loads of storage space with professionally organized closets, floor to ceiling windows exposing great... View all property information
    Location Information
    Chicago, Illinois 60601
    1 / 23
    Near North Side
    Studio, 1 Bathroom, Sleeps 2 | Quick View
    From
    $2,750
    / Month
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    • DVD Player
    • Shared Outdoor Pool...
    • Washer
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Stunning Space Features wall to wall upgraded plush carpeting, beautiful open kitchen with granite countertops and stainless steel appliances, massive walk in closet with loads of storage space, floor to ceiling windows exposing eastern peak-a-boo lake views, beautifully updated bathroom, and w/d... View all property information
    Location Information
    Chicago, Illinois 60611
    1 / 15
    5 of 5 stars (2) Excellent
    Lakeview
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
    other travelers have booked this property
    From
    $195
    / Night
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    • DVD Player
    • Satellite TV
    • Air Conditioning
    • Washer
    • Waterfront
    • Patio
    • Grill
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Our vintage apartment is located in the beautiful Chicago neighborhood of Lakeview with many ethnic restaurants and clubs with-in walking distance. Try a different ethnic specialty every night of the week. The apartment is in an ideal location to come and explore Chicago. Stroll 2 blocks through... View all property information
    Location Information
    Chicago, Illinois 60657
    5 of 5 stars Reviewed December 12, 2013
    My husband and I and our dog, Mazie, had the best week during the week of thanksgiving. The house was so comfortable and homey and the neighborhood was a great place to walk a...
    5 of 5 stars Reviewed November 3, 2013
    Our family highly recommends "the Ginko Place". What a wonderful place! Where in Chicago can you stay and have a garden/patio BBQ in the middle of the City! Not only is a home...
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    1 / 9
    Northwest Side
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
    From
    $109
    / Night
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    • Parking
    • Satellite TV
    • Patio
    • Air Conditioning
    • Washer
    • Sauna
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    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
    Location Information
    Chicago, Illinois 60647
    1 / 17
    The Loop
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
    From
    $149
    / Night
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    • Internet Access
    • Air Conditioning
    • Sauna
    • Washer
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Please call/e-mail for more information. Beds: 2 Queen Beds View all property information
    Location Information
    Chicago, Illinois 60602
    1 / 22
    Near North Side
    Studio, 1 Bathroom, Sleeps 2 | Quick View
    From
    $3,600
    / Month
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    Amenities & Details
    • Washer
    • Shared Outdoor Pool...
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Amazing unit features wall to wall cherry hardwood floors, stunning kitchen with quartz countertops and snaidero cabinetry, loads of storage space with professionally organized closets, floor to ceiling windows exposing great Chicago River and city skyline views, beautifully updated marble... View all property information
    Location Information
    Chicago, Illinois 60601
    1 / 27
    Studio, 1 Bathroom, Sleeps 2 | Quick View
    From
    $2,500
    / Month
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    • Hot Tub
    • Washer
    • Shared Outdoor Pool...
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    White quartz countertops, two-tone cabinetry, Frigidaire stainless steel appliances, gas stoves and white glass mosaic tile backsplash Full size washer/dryer Custom designed wide plank flooring throughout Walk in closet Contemporary bath finishes Everything about the building has been considered;... View all property information
    Location Information
    Chicago, Illinois 60607
    The Loop
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
    From
    $400
    / Night
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    • Washer
    • Satellite TV
    • Housekeeping...
    • Wi-Fi
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    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 / 17
    5 of 5 stars (39) Excellent
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
    From
    $154
    / Night
    Payment Protection
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    Amenities & Details
    • Washer
    • Patio
    • Satellite TV
    • Internet Access
    • Balcony
    • Air Conditioning
    • Parking
    • Porch
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    City of Chicago Vacation LICENSE NO.: 2087699 This Vintage Early 1900’s 2-Flat 2nd floor apartment is in the beautiful tree-lined neighborhood of Andersonville. Located in the FUN, EXCITING, ECLECTIC ANDERSONVILLE Neighborhood on the north side of Chicago less than 2-blocks west of Clark Street... View all property information
    Location Information
    Chicago, Illinois 60640
    5 of 5 stars Reviewed August 24, 2015
    We stayed here during a family trip, and the apartment was absolutely beautiful. Even with a family of six, the apartment was more than spacious and accommodating. Every room was...
    5 of 5 stars Reviewed June 1, 2015
    Paul was a great host, responsive and clear. The location is so fantastic if you want to experience a charming Chicago neighborhood. Restaurants, bars, cafes, and shopping are...
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    Chicago Vacation Rentals

    Planning a visit to Chicago? A Chicago vacation rental is a great hotel alternative. From modern apartments on the Magnificent Mile to cozy coach houses in Lincoln Park and everything in between, we’ve got a wide variety of Chicago vacation rentals so there’s sure to be one that’s just right for you. Whatever your budget, we’ll help you find a great deal. Plus, you can book with confidence - we have plenty of unbiased user reviews of Chicago vacation rentals!

    Chicago family vacations

    Chicago is a great city for families and a vacation home rental makes it easy to explore all that the second city has to offer. If it’s baseball season, catch a Chicago Cubs game at historic Wrigley Field, one of the oldest ball parks in the country. Or take the kids out to Navy Pier, which features amusement rides, shops and restaurants right on Lake Michigan. If you’re kids are animal lovers, visit the Great Ape House at the Lincoln Park Zoo, where admission is still free. Or see dinosaurs at The Field Museum of Natural History.

    Chicago attractions

    There's plenty to do in Chicago and a vacation rental in the city will put you within walking distance of most of the city's many attractions. Art lovers will enjoy the Art Institute of Chicago where they can browse the large collection of impressionist and post-impressionist paintings before heading to the newer Modern Wing. After, you’ll want to head over to nearby Millennium Park, which features public art and cultural events year-round. During the warmer months, find a spot on the sand at Oak Street Beach, a great place to people watch with views of downtown skyscrapers and Lake Michigan.

    Chicago day trips

    For those who want to explore Chicago beyond the city center, there are plenty of short getaways worth exploring, all within an hour or two of your vacation rental. Nearby Oak Park is home to the Frank Lloyd Wright Home and Studio. It’s also the birthplace of Ernest Hemingway. For those looking for outdoor adventure, head south to Starved Rock State Park where you can hike miles of trails through rolling hills or go fishing, boating or horseback riding. Other popular getaways include Lake Geneva in southern Wisconsin or the shores along Lake Michigan outside the city.

    Saving money on Chicago vacation rentals

    Whether you want to stay in a chic downtown apartment rental in Chicago or a spacious house in the suburbs, we can help you find a deal that fits your budget. There are discounts on every type of property to help you get the most bang for your buck.