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Condos and vacation rentals in Chicago, IL

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    $159
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    1 / 11
    5 of 5 stars (1) Excellent
    Roscoe Village
    2 Bedrooms / 1 Bathroom / Sleeps 6
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    $120
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    1 / 28
    4 of 5 stars (5) Very good
    Rogers Park
    2 Bedrooms / 1 Bathroom / Sleeps 7
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    $265
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    1 / 10
    5 of 5 stars (1) Excellent
    3 Bedrooms / 1 Bathroom / Sleeps 5
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    1 / 9
    4 of 5 stars (1) Very good
    3 Bedrooms / 1 Bathroom / Sleeps 6
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    • x
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    About this property
    3 Bedroom/1 Bath apartmentt located in the North Center neighborhood…Sleeps 6 Just 2 blocks from the train...A quick walk to Chicago's Brown Line 'L'...take the train downtown...or to Wrigley Field (you can walk, too) from this North Center location... Walk to everything...restaurants... Sola,... View all property information
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    4 of 5 stars Reviewed July 3, 2014
    Maison excellente !!!! Très propre, très fonctionnelle. Elle convient très bien pour être entre amis ou une famille. Clim, lave vaisselle, lave linge, sèche linge : tout est super...
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    1 / 6
    4 of 5 stars (1) Very good
    2 Bedrooms / 1 Bathroom / Sleeps 3
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    • x
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    About this property
    This is an English Garden apartment...3 steps down... in an extra wide Greystone building, this charming two bedroom offers plenty of light, lots of closet space, hardwood floors and private entrance with vestibule & foyer... kitchen w/dishwasher & microwave. Fully furnished, utilities included... View all property information
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    4 of 5 stars Reviewed August 17, 2014
    I rented the garden unit of this house just north of Chicago. I was traveling with my 13-yr.old grandson and wanted separate bedrooms. The apartment was very clean and fully...
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    $550
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    1 / 18
    DePaul
    4 Bedrooms / 4 Bathrooms / Sleeps 24
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    • Smoking allowed
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    • ?
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    About this property
    Temporarily live in the best neighborhood in Chicago in an 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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    $189
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    1 / 16
    5 of 5 stars (35) Excellent
    3 Bedrooms / 1 Bathroom / Sleeps 6
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    • Air Conditioning
    • Balcony
    • Dryer
    • Fireplace
    • Internet Access
    • Safe
    • Satellite TV
    • Washer
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    • 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
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    4 of 5 stars Reviewed December 29, 2014
    Enjoyed our stay! Plenty of space and amenities. Easy street parking. Three comfy beds, well stocked kitchen, plenty of towels. Could have used a little stronger internet and...
    4 of 5 stars Reviewed October 4, 2014
    I rented this apartment for some friends who were visiting me. The location was excellent since I live nearby. It is also very close to Andersonville. The street is quiet and the...
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    1 / 37
    4 of 5 stars (5) Very good
    Near North Side
    2 Bedrooms / 2 Bathrooms / Sleeps 5
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    • Air Conditioning
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    • Satellite TV
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    • Water Views
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    • Pets allowed
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    • Suitable for children
    • x
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    • ?
    About this property
    Studio Apartment Downtown Chicago Millennium Park walking distance most attractions close to public transportation... View all property information
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    4 of 5 stars Reviewed August 18, 2014
    Very strategic location near to major attractions. Very spacious and quiet. The best coffee is just down the building! The only thing was the wifi was extremely slow, me and my...
    3 of 5 stars Reviewed July 1, 2014
    security was not aware of our check in and had to call and verify. kitchen is not adequately stocked for those who may use knives, forks and wine glasses. it was, however...
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    1 / 14
    The Loop
    1 Bedroom / 1 Bathroom / Sleeps 2
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    • Internet Access
    • Ocean Views
    • Satellite TV
    • Shared Indoor Pool
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    About this property
    Located in the chic New Eastside near Millennium Park, The Art Institute and fabulous Michigan Avenue shopping, this one-bedroom, lakefront condo is furnished with all the luxuries of a five-star hotel: Sleep Number queen bed, Nespresso coffee maker, digital television, pool, gym, rooftop views of... View all property information
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    $85
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    1 / 16
    5 of 5 stars (32) Excellent
    Northwest Side
    1 Bedroom / 1 Bathroom / Sleeps 2
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    • Air Conditioning
    • Dryer
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    • Satellite TV
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    • Pets allowed
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    • Suitable for children
    • x
    • x
    • x
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    • Elder access
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    About this property
    A big thank you to my guests for their great reviews. I'm so honored to have earned a 2014 Certificate of Excellence from tripadvisor! Very comfortable, private lower level of duplex. Perfect for a business traveler who doesn't want to be downtown, or a couple visiting the city for pleasure.... View all property information
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    4 of 5 stars Reviewed December 10, 2014
    Cheryl's apartment worked perfectly as a home base for my husband and me during a long weekend's visit to Chicago. We spent much of our time in and around the Loop, but found the...
    5 of 5 stars Reviewed November 14, 2014
    My husband and I rented the apartment for 5 days in early November. I was attending a Conference downtown and did not want to pay the high price hotel. This place was perfect...
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    1 / 18
    4 of 5 stars (1) Very good
    The Loop
    Studio / 1 Bathroom / Sleeps 2
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    • ?
    About this property
    Studio Apartment Downtown Chicago Millennium Park walking distance most attractions close to public transportation... View all property information
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    4 of 5 stars Reviewed August 20, 2014
    Tr`es bien situé, propre et bien équipé. Personnel de l'immeuble bien chaleureux. Pitsfield's café `a ne pas manqué au rez-de-chaussée. Calme , bien insonorisé...`a l'exeption de...
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    1 / 14
    4.5 of 5 stars (3) Very good
    Studio / 1 Bathroom / Sleeps 2
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    • Air Conditioning
    • Dryer
    • Internet Access
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    • Wi-Fi
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • x
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    • Elder access
    • x
    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
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    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...
    5 of 5 stars Reviewed July 8, 2014
    the location of the apartment we stayed was convenient enough:only some min away from the red line train and a min from the bus stop,so getting to downtown is easy.we got a great...
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    $195
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    1 / 15
    5 of 5 stars (2) Excellent
    Lakeview
    2 Bedrooms / 1 Bathroom / Sleeps 6
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    • Air Conditioning
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    • Satellite TV
    • Washer
    • Waterfront
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
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    • Wheelchair access
    • 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
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    $250
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    1 / 13
    5 of 5 stars (1) Excellent
    Near North Side
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Pets allowed
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    • Suitable for children
    • ?
    • x
    • ?
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    • x
    About this property
    Located a block north of the Chicago River this property features a prime location just steps from Michigan Avenue. Amenities include gym, pool, and hot tub. Two queen size beds and a fold out sleeper sofa make it possible to sleep six. Chicago's premier downtown Streeterville neighborhood grants... View all property information
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    5 of 5 stars Reviewed January 28, 2015
    My fiancé and I really enjoyed ourselves here!! It was everything we were looking for in a nice condo for a mini getaway. We walked right out our condo and BOOM there was...
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    1 / 36
    2 Bedrooms / 1 Bathroom / Sleeps 5
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    • Air Conditioning
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
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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
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    $197
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    1 / 7
    5 of 5 stars (1) Excellent
    Northwest Side
    2 Bedrooms / 2 Bathrooms / Sleeps 8
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    • Air Conditioning
    • Dishwasher
    • Hot Tub
    • Internet Access
    • Safe
    • Satellite TV
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    Two bedrooms, two bathrooms condo apartment on the north side of Chicago. The apartment can accommodate 4 guests comfortably, but if need be can add two inflatable mattresses to accommodate up to 8 people. FREE Wireless internet access. FREE parking on public street in front of the building.... View all property information
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    $115
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    1 / 23
    2.5 of 5 stars (4) Poor
    Northwest Side, Wicker Park / Bucktown
    2 Bedrooms / 1 Bathroom / Sleeps 4
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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
    The Chicago Bathhouse Corporate Residences are located on the 2nd floor of a 2 story building in Wicker Park Chicago. This vacation rentals are 2 bedrooms, 1 bathroom, 10 minutes from Chicago downtown. Close to restaurants, cafes. 5 min walk to Blue Line which takes you Downtown in 10 min... View all property information
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    2 of 5 stars Reviewed October 14, 2014
    I felt like I was being punked! When I booked this place it advertised access to the spa at the bath house. When we arrived the curt "receptionist" said access was only for one...
    3 of 5 stars Reviewed June 15, 2014
    This apartment in Wicker Park is enormous and very nice! It's in a pretty sweet location above a bathhouse and next to a great breakfast place called Milk & Honey. The el is about...
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    1 / 16
    Roscoe Village
    2 Bedrooms / 1 Bathroom / Sleeps 6
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    • Suitable for children
    • 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
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    $225
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    1 / 9
    3 Bedrooms / 1 Bathroom / Sleeps 5
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    • Suitable for children
    • x
    • x
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    • x
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    About this property
    Convenience is Key! A quick walk to Chicago's Brown Line 'L'...take the train downtown...or to Wrigley Field (you can walk, too) from this North Center location... Walk to everything...restaurants... Sola, Brown Trout, Mrs. Murphy's, Snappy's...to name a few! Shop at Trader Joe's, Jewel &... View all property information
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    $311
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    1 / 30
    Lakeview
    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Suitable for children
    • x
    • x
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    • x
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    About this property
    CHICAGO GUEST HOUSE Tripadvisor Certificate of Excellence 2014 5.0 of 5 stars --133 Reviews Ranked #1 of 51 Specialty Lodging in Chicago! 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... View all property information
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    $165
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    1 / 6
    1 Bedroom / 1 Bathroom / Sleeps 4
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    • Suitable for children
    • x
    • x
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    • x
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    About this property
    This unit sleeps up to 4(four) guests maximum... I have additional units if you need more beds!! Please be sure to view my other units: Please view my other units: #2936706, #2936829, #2937555, #2936763 and #2937588...hope to see you soon! Bright and inviting…large 1 bedroom in LINCOLN SQUARE.... View all property information
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    1 / 9
    2 Bedrooms / 1 Bathroom / Sleeps 6
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    • Air Conditioning
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    • Satellite TV
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    • Smoking allowed
    • Suitable for children
    • x
    • x
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    • Elder access
    • x
    • ?
    About this property
    Gracious duplex with comforts of home. This unit has 1 full bath on upstairs level and a powder room on the main level. Fully equipped eat in kitchen with breakfast bar. Cable, wireless internet. Convenience is Key! A quick walk to Chicago's Brown Line 'L'...take the train downtown...or to... View all property information
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    1 / 20
    3 Bedrooms / 1 Bathroom / Sleeps 4
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    • x
    • x
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    • x
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    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
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    $70
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    1 / 15
    Rogers Park
    3 Bedrooms / 1 Bathroom / Sleeps 8
    travelers have booked this property
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    • Air Conditioning
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    • Internet Access
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    Perfect Home while visiting Chicago for a few days or longer stays, perfect for family gatherings, vacation, wedding stays, or simply enjoying time in The city. Walking distance to lots and public transportation! THE UNIT Lots of natural light due to the unit being on the top floor of nice and... View all property information
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    $150
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    1 / 9
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    travelers have booked this property
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    • Air Conditioning
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    • Fireplace
    • Hot Tub
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    • Satellite TV
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • x
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    • Elder access
    • x
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    About this property
    Large, roomy two bedroom loft like apartment tastefully appointed and furnished. Hardwood floors and ceramic tiles in kitchen and bathroom. Plenty of sitting room with large screen TV, fireplace and free WiFi. Two full bedrooms, one with a king sized and the other with a queen sized bed. You... View all property information
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    1 / 34
    Lincoln Square
    5 Bedrooms / 5 Bathrooms / Sleeps 12
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    • Air Conditioning
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    • Hot Tub
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    • Satellite TV
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    Huge 5 Bedroom-4.5 Bathroom home, 4 fire places, completely remodeled, fully furnished. Equipped kitchen with large breakfast island, separate dining room seating 8-10. Family room off the kitchen with fire place, huge deck and private back yard. Huge master bedroom with decorative fire place,... View all property information
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    1 / 23
    Rogers Park
    3 Bedrooms / 1 Bathroom / Sleeps 8
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    • x
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    • Elder access
    • x
    About this property
    Perfect Home while visiting Chicago for a few days or longer stays, perfect for family gatherings, vacation, wedding stays, or simply enjoying time in The city. Walking distance to lots and public transportation! THE UNIT Lots of natural light due to the unit being on the top floor of nice and... View all property information
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    $120
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    1 / 23
    Northwest Side
    2 Bedrooms / 1 Bathroom / Sleeps 4
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    • Pets allowed
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    • x
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    About this property
    Live like a native in this artist-owned, artist-occupied vintage building located between the leading edge of the trendy Logan Square restaurant nexus and the old Polish neighborhood. Furnished in rustic Modern finds, it's on the Blue Line with easy access to the Loop and O'Hare. The unit has two... View all property information
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    $167
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    1 / 13
    Northwest Side
    2 Bedrooms / 1 Bathroom / Sleeps 4
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    • Air Conditioning
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    • Dishwasher
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    • Satellite TV
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    Two bedrooms, one bathroom condo apartment on the north side of Chicago. The apartment can accommodate 4 guests comfortably, but if need be can add two inflatable mattresses to accommodate up to 8 people. FREE Wireless internet access. FREE parking on public street in front of the building. Bus... View all property information
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    $375
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    1 / 35
    5 of 5 stars (1) Excellent
    Lakeview
    3 Bedrooms / 2 Bathrooms / Sleeps 8
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    • Pets allowed
    • Smoking allowed
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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 and character! A Vintage Beauty With All the Modern Comforts & Amenities.... View all property information
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    5 of 5 stars Reviewed July 26, 2014
    What a perfect place for a family get away. The Clark Suite was perfect for our family of 7 adults. The kitchen was immaculate and well equipped with anything you needed. I...
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    Northwest Side
    4 Bedrooms / 4 Bathrooms / Sleeps 10
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    • Air Conditioning
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    About this property
    Enjoy the entire house for a fraction of any hotel. Our house is a 10 room, 4 Bedroom, 3.5 Bathroom. Completely remodeled with huge fully equipped kitchen open to family room, perfect for entertaining, two story master suite with steam shower, double marble vanity, huge Jacuzzi, two walk in... View all property information
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    1 / 15
    Northwest Side
    2 Bedrooms / 1 Bathroom / Sleeps 4
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    About this property
    Enjoy a great urban experience staying in the Ukrainian Village of Chicago! -- 2 bedroom flat perfect for short term stays. Convenient to shops, grocery, restaurants, library, bars, gym, swimming pool! THE SPACE: This main floor apartment includes the following amenities: Two comfortable bedrooms... View all property information
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    1 / 18
    Rogers Park
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    • x
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    About this property
    Nice and bright 2 bedroom 2 bath condominium two blocks from the lake and one block from train, bus, restaurants and coffee shops. Unit is cozy, spacious and conveniently located on first floor, with washer and dryer. Hardwood floors. LOCATION The unit is located on East Rogers Park, two blocks... View all property information
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    1 / 10
    DePaul
    3 Bedrooms / 1 Bathroom / Sleeps 6
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    About this property
    HISTORY: Aster House has been renting since 1891, and under the present owners since 1982. We've had guests return as long as 18 years, so you may be assured of a safe secure visit. NEIGHBORHOOD: Aster House is on a quiet residential street in Lincoln Park, Chicago's most upscale downtown... View all property information
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    1 / 10
    5 of 5 stars (1) Excellent
    The Loop
    1 Bedroom / 1 Bathroom / Sleeps 4
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    • Pets allowed
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    This 39-story Chicago hotel is across the river from Magnificent Mile shopping, six blocks from Lake Michigan, and a half-mile from the Loop's theater district and the Art Institute of Chicago. Located on the Magnificent Mile. Industry and creativity converge in Chicago, the birthplace of the... View all property information
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    5 of 5 stars Reviewed December 2, 2014
    For downtown Chicago stay, this was fantastic...lots of room and great location! We were a walk away from anything...from Navy Pier to the beach to shopping to family museums. A...
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    5 of 5 stars (13) Excellent
    Southwest Side
    2 Bedrooms / 1 Bathroom / Sleeps 6
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    • Pets allowed
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    • Suitable for children
    • x
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    About this property
    We have two really incredible vacation rental apartments. The view in our first picture is our large hot tub. It's your new best friend after a day of travel, sightseeing, or business. The next photo is the amazing Chicago City Skyline view from our deck (closed in winter when there is snow... View all property information
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    5 of 5 stars Reviewed April 7, 2014
    Our family of four (two teens) spent 5 days here during spring break and had an excellent experience. We went downtown every day by catching the red line train at the 35th/Sox...
    5 of 5 stars Reviewed May 2, 2012
    We couldn’t be more pleased with our stay, everyone had a fantastic time. Our visit took place April 12-15 and there were six of us; my parents (early 50’s), younger brother and...
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    5 of 5 stars (30) Excellent
    Southwest Side
    3 Bedrooms / 1 Bathroom / Sleeps 6
    travelers have booked this property
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    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Hot Tub
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
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    About this property
    We have two really incredible vacation rental apartments. The view in our first picture is our large hot tub. It's your new best friend after a day of travel, sightseeing, or business. The next photo is the amazing Chicago City Skyline view from our deck (closed in winter when there is snow... View all property information
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    5 of 5 stars Reviewed November 13, 2014
    Our family of four had an excellent time at this apartment. Bob was very easy to deal with and extremely helpful. Key code access to the apartment was very convenient. A garage...
    4 of 5 stars Reviewed September 27, 2014
    We were very pleased with our stay at this facility. It isn't in the typical touristy area which we liked as it made our urban experience feel more authentic and any neighbors we...
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    1 / 23
    5 of 5 stars (17) Excellent
    3 Bedrooms / 2 Bathrooms / Sleeps 10
    travelers have booked this property
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    • Air Conditioning
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    • Suitable for children
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    About this property
    Spacious Bright Loft in the Heart of Everything Chicago 2 -10 adults, up to 12 with children Our funky warehouse & former tavern turned costume factory turned fabulous Lincoln Park home can be your home away from home in Chicago. Located in Chicago's newest neighborhood - 'SONO', at the... View all property information
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    5 of 5 stars Reviewed November 24, 2014
    We stayed during the Chicago marathon. The apartment is very conveniently located to the subway so that we could get everywhere we needed to during our stay. My favorite part of...
    5 of 5 stars Reviewed November 24, 2014
    My friends made all the arrangements on where to stay and they couldn't have picked a better place. I loved the location and the living space we had. I am not much of a writer...
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    1 / 14
    5 of 5 stars (9) Excellent
    Northwest Side
    2 Bedrooms / 1 Bathroom / Sleeps 4
    travelers have booked this property
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    • Air Conditioning
    • Balcony
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    • Pets allowed
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    • Suitable for children
    • x
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    About this property
    This is a nice place on a quiet street, close to transportation and many restaurants. Very close to I 94. View all property information
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    5 of 5 stars Reviewed March 2, 2015
    I really thank god i found this place. I had my family in from out of town and this was great. Hanna & her husband was very nice & helpful, anything we needed they accomodated us...
    5 of 5 stars Reviewed January 12, 2015
    The rental was EXCEPTIONAL! The Hannn was so nice and the unit couldn't have been better! My family absolutely loved it! Thanks again!
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    5 of 5 stars (8) Excellent
    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Fireplace
    • Hot Tub
    • Internet Access
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
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    About this property
    Beautifully furnished Three Bedroom, Two Bath. Walking distance from the lakefront, and a short bus ride to Michigan Avenue. First Floor Condominium Unit, New Oak Floors, Granite Counters, Marble Baths. Stainless Steel Brand New Appliances. In Unit, Washer, Dryer. Three Large Bedrooms. Master Bath... View all property information
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    5 of 5 stars Reviewed October 7, 2014
    The condo is all that it is advertised. The neighborhood is quiet and the condo is well appointed with all of amenities for you to enjoy your stay. The hardwood floors are a nice...
    5 of 5 stars Reviewed June 10, 2014
    This condo fit our needs perfectly. My wife and I were staying with our young daughter and going to 3 Cubs games. It was great every night to be able to come back to this place...
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    5 of 5 stars (1) Excellent
    Northwest Side
    1 Bedroom / 1 Bathroom / Sleeps 2
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    • x
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    About this property
    If you are looking for a private, cozy, and comfortable place then this is just right for you. Here you can relax and lay back in a newly renovated unit with a private entrance for your convenience. Let the travel stress behind you and enjoy your stay in that great City we call HOME, Chicago We... View all property information
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    4 of 5 stars (2) Very good
    3 Bedrooms / 1 Bathroom / Sleeps 8
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    • Garden or Yard
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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. It has 3 Bedrooms, 1 Bathroom, Living Room, Dining Room and Full Kitchen. If you enjoy a quiet home with newer beds, clean sheets and towels, spaces, privacy, kitchen, laundry,... View all property information
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    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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    4.5 of 5 stars (4) Very good
    1 Bedroom / 1 Bathroom / Sleeps 6
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    • x
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    About this property
    Plenty of free street parking is available on our block. This is the first floor of our home so we expect all guests to be QUIET & respectful. If you love to party, stomp around and yell then this is not the place for you. No parties, no loud music & no stumbling in drunk at 2 am. We are old &... View all property information
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    4 of 5 stars Reviewed September 3, 2014
    This was my first experience using Trip Advisor and renting a private home to stay in. The weekend was great. The apartment was located in a safe neighborhood to walk around in...
    5 of 5 stars Reviewed November 11, 2013
    From start to finish this rental was perfect. I was hesitant to rent from a private party, however great communication early on helped put me at ease. As a solo traveling female I...
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    5 of 5 stars (1) Excellent
    Lakeview
    1 Bedroom / 1 Bathroom / Sleeps 2
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    • Pets allowed
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    • x
    • x
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    • x
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    About this property
    This is a beautiful garden unit. It comes fully furnished with a queen size bed plus a pull-out couch. Plenty of sitting room, updated bathroom, does not have kitchen but does have small fridge, microwave and coffee maker. The location is ideal, being close to the city and still in a quiet... View all property information
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    5 of 5 stars Reviewed October 13, 2014
    My wife and I spent 3 night here in Sept 2014. The owner was very friendly and helpful. This studio is located in a nice quiet neighborhood, close to restaurants and shops, and...
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    Lincoln Square
    3 Bedrooms / 2 Bathrooms / Sleeps 6
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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
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    1 / 12
    5 of 5 stars (1) Excellent
    Near North Side
    1 Bedroom / 1 Bathroom / Sleeps 4
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    • x
    • x
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    About this property
    Whether you are coming to stay at Raffaello Chicago for business, a romantic getaway, or traveling with your family and friends, we have the perfect accommodation ready and waiting for you. Every Raffaello guest room reflects an upscale European style with soothing accents, subtle earth tones and... View all property information
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    5 of 5 stars Reviewed February 27, 2015
    We were lucky that we chose this place. It is in a perfectly managed hotel , Raffaello Hotel . Everything was ready to have a nice stay. Thanks
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    4.5 of 5 stars (2) Very good
    3 Bedrooms / 1 Bathroom / Sleeps 8
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    • Air Conditioning
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    • x
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    About this property
    This is a 3 Bed Room apartment of a two flat brick building in Andersonville area of Chicago. This apt has: 3 bedrooms, sleeps 8 Air Conditioners Free cell phone for international guests (plus deposit) Eat-in Kitchen Living Room Full size fridge Free parking Free laundry Complete kitchen Living... View all property information
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    4 of 5 stars Reviewed July 10, 2014
    I really enjoyed staying here. A great property. The sink did break while we were there but Jackie was right on getting it fixed for us! Great place, big enough for our group!
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    4.5 of 5 stars (2) Very good
    Northwest Side
    2 Bedrooms / 2 Bathrooms / Sleeps 5
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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
    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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    5 of 5 stars Reviewed August 17, 2014
    Nice apartment for up to 6 people, around $20 taxi ride from the Airport. Close to a large park, bus, and train stations. We purchased 7 days CTS passes for $33 each with...
    4 of 5 stars Reviewed March 29, 2014
    Bed was a little uncomfortable and broke often. Parking was difficult. Clean apartment, ideal for a large family
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    4.5 of 5 stars (3) Very good
    Lakeview
    2 Bedrooms / 1 Bathroom / Sleeps 5
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    • Air Conditioning
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    • x
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    About this property
    Spacious, elegantly appointed and furnished Lakeview vacation/executive two bedroom, one bathroom apartment. First floor on a quiet tree-lined street, the entire apartment features; either oak floors or ceramic tiles, all solid oak doors and windows and oriental rugs. You will find our... View all property information
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    5 of 5 stars Reviewed February 4, 2015
    Good value for the money. We enjoyed the player piano. Beds were comfortable and everything was clean.
    4 of 5 stars Reviewed July 28, 2014
    Close to transit & grocery. Lots of space. Communication with Andy was great. He answered any questions we had before the trip in a timely manner. Easy check in and out...
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    3.5 of 5 stars (3) Average
    1 Bedroom / 1 Bathroom / Sleeps 2
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    • Pets allowed
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    • Suitable for children
    • x
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    • x
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    About this property
    Charming, roomy one bedroom , with open kitchen and living space. This recently refurbished loft-style apartment gives visitors to Chicago a chance to visit and explore whist enjoying the comforts of modern living. Hardwood floor, and ceramic tiles in kitchen and bathroom. Plenty of sitting... View all property information
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    4 of 5 stars Reviewed September 16, 2014
    The accommodations were not real fancy but well suited for a busy stay in Chicago! Excellent location for the price. Wrigley and other top sites are easily accessible. If you are...
    3 of 5 stars Reviewed June 15, 2014
    Ok so if you're expecting a pretty little getaway in Chicago with views and a location then this place isn't for you. The apartment is located atop of a commercial building that's...
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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.