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Condos and vacation rentals in Chicago, IL

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From
$159
Per Night
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1 / 11
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Roscoe Village
2 Bedrooms, 1 Bathroom, Sleeps 6
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$99
Per Night
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1 / 14
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Northwest Side
2 Bedrooms, 1 Bathroom, Sleeps 4
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$130
Per Night
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1 / 16
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DePaul
2 Bedrooms, 1 Bathroom, Sleeps 6
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From
$120
Per Night
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1 / 14
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DePaul
2 Bedrooms, 1 Bathroom, Sleeps 4
Bookings
Details Reviews (2) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
This Unit has one regular sized bedroom and a 'Lil' bedroom - twin bed only. Located 1 block from the Fulllerton L stop (Brown Purple & Red Line service), getting around the Windy City is a breeze. Magnificent Mile in under 10 minutes, the Loop (Grant Park, Millennium Park, Museum Row) in 12. With... View all property information
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From
$189
Per Night
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1 / 16
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3 Bedrooms, 1 Bathroom, Sleeps 6
Details Reviews (35) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dryer
  • Fireplace
  • Internet Access
  • Safe
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • 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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From
$550
Per Night
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1 / 18
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DePaul
4 Bedrooms, 4 Bathrooms, Sleeps 24
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Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
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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From
$150
Per Night
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1 / 11
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DePaul
2 Bedrooms, 1 Bathroom, Sleeps 6
Bookings
Details Reviews (2) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • 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 AUTO BOOK FOR PERIODS SHORTER THAN WHAT IS REQUIRED AS THE BOOKING MAY NOT BE HONORED. PLEASE EMAIL OR CALL WITH ANY QUESTIONS.... View all property information
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From
$75
Per Night
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1 / 18
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The Loop
Studio, 1 Bathroom, Sleeps 2
Booking
Details Reviews (1) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Wi-Fi
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • ?
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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From
$375
Per Night
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1 / 32
Lakeview
3 Bedrooms, 2 Bathrooms, Sleeps 8
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Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
CHICAGO GUEST HOUSE Tripadvisor Certificate of Excellence 2014 5.0 of 5 stars --128 Reviews on TRIPADVISOR Ranked #1 of 51 Specialty Lodging in Chicago! ************************* Beautiful & spacious--filled with charm 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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From
$125
Per Night
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1 / 37
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Near North Side
2 Bedrooms, 2 Bathrooms, Sleeps 5
Bookings
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Amenities & Details
  • Air Conditioning
  • Internet Access
  • Satellite TV
  • Washer
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • ?
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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From
$99
Per Night
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1 / 14
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DePaul
1 Bedroom, 1 Bathroom, Sleeps 3
Bookings
Details Reviews (4) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
About this property
NOTE This calendar is updated weekly not daily. Please visit www.LincolnParkVacationRentals.com for the most accurate information or email inquiry@lincolnparkvacationrentals.com to inquire about this or our other units at the same location. Please also note that holiday weeks and special event... View all property information
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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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From
$80
Per Night
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1 / 14
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Studio, 1 Bathroom, Sleeps 2
Bookings
Details Reviews (3) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dryer
  • Internet Access
  • Washer
  • Wi-Fi
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • x
  • Wheelchair access
  • 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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From
$99
Per Night
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1 / 7
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Northwest Side
1 Bedroom, 1 Bathroom, Sleeps 2
Bookings
Details Reviews (1) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dryer
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
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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From
$199
Per Night
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1 / 15
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Near North Side
2 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
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Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
  • 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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$200
Per Night
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1 / 22
Lakeview
2 Bedrooms, 1 Bathroom, Sleeps 4
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Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Grill
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
An irresistibly charming apartment! Good things do come in small packages! Walk in to the home and the first thing you notice is nothing has been taken for granted. You’ll be engulfed in warm inviting hues. The beauty & integrity of the historic homerecaptured; undeniably charming. Glance around... View all property information
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From
$80
Per Night
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1 / 17
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Northwest Side
2 Bedrooms, 1 Bathroom, Sleeps 4
Bookings
Details Reviews (1) Make Inquiry
Amenities & Details
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Washer
  • Wi-Fi
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • Wheelchair access
  • Elder access
  • ?
About this property
1100 sq feet of your own space! Lots of room to stretch out here, two bedrooms with queen-sized beds, an office, living room, den, full kitchen, one bathroom, laundry in unit, back deck, backyard with apple tree (apples!!!), Keurig coffee maker, and parking right out front! Queen sized air... View all property information
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5 of 5 stars Reviewed February 8, 2015
This is a two bedroom apartment on the first floor on a quiet street two blocks from Humboldt Park. We arrive in two days after the big blizzard, and the sidewalk was nicely...
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$79
Per Night
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1 / 14
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Northwest Side
Studio, 1 Bathroom, Sleeps 2
Bookings
Details Reviews (9) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dryer
  • Grill
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
The studio is situated in the couch house of the property. It is 300 square feet plus the bathroom. Beautiful decorated and very quiet place with the windows facing the beautiful garden. There is a washer and dryer on side and we can offer also breakfast. View all property information
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5 of 5 stars Reviewed September 20, 2014
The place is immaculate. Super clean and fully equipped. The location is great. You have the subway blue line (to downtown) in a short walk from the house to the station. The...
5 of 5 stars Reviewed September 1, 2014
I enjoyed my stay here and the hosts are warm, friendly and welcoming people. Hanne is just the sweetest person and I feel as if I have known her for many years. She always made...
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From
$115
Per Night
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1 / 23
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Northwest Side, Wicker Park / Bucktown
2 Bedrooms, 1 Bathroom, Sleeps 4
Bookings
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Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • 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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From
$199
Per Night
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1 / 16
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Roscoe Village
2 Bedrooms, 1 Bathroom, Sleeps 6
Booking
Details Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • 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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From
$150
Per Night
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1 / 9
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2 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
Details Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Fireplace
  • Hot Tub
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
  • x
About this property
Large, roomy two bedroom loft like apartment tastefully appointed and furnished. Hardwood floors and ceramic tiles in kitchen and bathroom. Plenty of sitting room with large screen TV, fireplace and free WiFi. Two full bedrooms, one with a king sized and the other with a queen sized bed. You... View all property information
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From
$120
Per Night
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1 / 7
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Northwest Side
2 Bedrooms, 1 Bathroom, Sleeps 4
Details Make Inquiry
Amenities & Details
  • Air Conditioning
  • Internet Access
  • Safe
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
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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From
$1,000
Per Week
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1 / 7
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Northwest Side
2 Bedrooms, 1 Bathroom, Sleeps 3
Details Make Inquiry
Amenities & Details
  • Air Conditioning
  • Hot Tub
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Perfect for short term stays in a great neighborhood. Available For weekly or monthly rentals Furnished for comfort and design, price includes all utilities and everything you need This completely furnished apartment is 1/2 block from the chicago avenue bus line, which runs straight to the blue... View all property information
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From
$79
Per Night
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1 / 12
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Northwest Side
Studio, 1 Bathroom, Sleeps 2
Details Make Inquiry
Amenities & Details
  • Air Conditioning
  • Fireplace
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
This studio is situated in the garden of the property. Very quiet and peaceful setting. It has a Murphy bed and a jacuzzi. View all property information
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From
$175
Per Night
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1 / 22
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The Loop
2 Bedrooms, 2 Bathrooms, Sleeps 10
Details Make Inquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Hot Tub
  • Internet Access
  • Washer
  • Wi-Fi
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • Wheelchair access
  • Elder access
  • x
  • x
About this property
Enjoy all that Chicago has to offer and then come home and relax on the huge (20 x20) deck with the best skyline views in the city. This is a charming Condo in the perfect location. Have the neighborhood feel with dozens of great places to go for a bite to eat within a couple blocks, and also... View all property information
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From
$237
Per Night
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1 / 10
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The Loop
1 Bedroom, 1 Bathroom, Sleeps 4
Bookings
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Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
About this property
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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From
$120
Per Night
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1 / 23
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Northwest Side
2 Bedrooms, 1 Bathroom, Sleeps 4
Booking
Details Make Inquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
  • ?
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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From
$218
Per Night
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1 / 11
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2 Bedrooms, 2 Bathrooms, Sleeps 6
Details Make Inquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Gym
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • Wheelchair access
  • Elder access
About this property
Our suite features Two Bedrooms/Two Bathrooms with a pull out couch and can accommodate six guests. Suite also contains fully equipped gourmet kitchen and is perfect for families or individuals, traveling for business or pleasure. The Guesthouse Hotel offers great style, comfort and value. Stay... View all property information
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From
$395
Per Night
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1 / 8
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DePaul
3 Bedrooms, 1 Bathroom, Sleeps 6
Booking
Details Make Inquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Safe
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
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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From
$120
Per Night
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1 / 28
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Rogers Park
2 Bedrooms, 1 Bathroom, Sleeps 7
Bookings
Details Reviews (5) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dryer
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
This listing is for a private 2-bedroom apartment in the Rogers Park neighborhood of Chicago. The apartment is over 1200 square feet (111 sq meters) and has tall 9.5' ceilings (2.9 meters), a marble bath, and hardwood floors throughout. There is also a charmingly retro yet fully functional kitchen... View all property information
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5 of 5 stars Reviewed January 1, 2015
Lisa and Caitlin did such an amazing job making the home comfortable and I loved the books about Chicago and the Book they had made with so much helpful information! The location...
4 of 5 stars Reviewed October 2, 2014
Three of us stayed at at Devon property and were thrilled with the accommodations. The location to the local bus and train stops were very convenient. The hosts, Lisa and...
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From
$165
Per Night
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1 / 22
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Lincoln Square
3 Bedrooms, 2 Bathrooms, Sleeps 6
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Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
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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From
$95
Per Night
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1 / 10
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Lakeview
1 Bedroom, 1 Bathroom, Sleeps 2
Bookings
Details Reviews (1) Make Inquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
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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From
$200
Per Night
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1 / 8
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Northwest Side
2 Bedrooms, 2 Bathrooms, Sleeps 5
Bookings
Details Reviews (2) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dryer
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
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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From
$139
Per Night
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1 / 14
Payment Protection
3 Bedrooms, 1 Bathroom, Sleeps 8
Bookings
Details Reviews (2) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dryer
  • Garden or Yard
  • Internet Access
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • Wheelchair access
  • Elder access
  • ?
  • ?
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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From
$195
Per Night
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1 / 15
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Lakeview
2 Bedrooms, 1 Bathroom, Sleeps 6
Bookings
Details Reviews (2) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
  • Waterfront
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • 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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From
$300
Per Night
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1 / 6
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3 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
Details Reviews (8) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Fireplace
  • Hot Tub
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
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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From
$99
Per Night
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1 / 20
Payment Protection
1 Bedroom, 1 Bathroom, Sleeps 6
Bookings
Details Reviews (4) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Internet Access
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
About this property
Plenty of free street parking is available on our block. This apt is very big and had a has a lot of natural sunlight. Located on the first floor of our building. We live upstairs in a completely separate apt so we are very close if you have any questions or concerns, but your privacy is assured.... 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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From
$149
Per Night
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1 / 10
Payment Protection
3 Bedrooms, 1 Bathroom, Sleeps 8
Bookings
Details Reviews (2) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dryer
  • Housekeeping...
  • Internet Access
  • Safe
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • Wheelchair access
  • Elder access
  • x
  • x
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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From
$225
Per Night
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1 / 11
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Lakeview
2 Bedrooms, 1 Bathroom, Sleeps 5
Bookings
Details Reviews (3) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
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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From
$90
Per Night
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1 / 6
Payment Protection
1 Bedroom, 1 Bathroom, Sleeps 2
Bookings
Details Reviews (3) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dryer
  • Hot Tub
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
  • x
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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From
$120
Per Night
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1 / 4
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The Loop
1 Bedroom, 1 Bathroom, Sleeps 1
Details Make Inquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
  • x
About this property
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From
$250
Per Night
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1 / 14
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West Town
3 Bedrooms, 2 Bathrooms, Sleeps 5
Bookings
Details Reviews (4) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Safe
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
An Urban Oasis! This sophisticated end unit, 3-story townhome features exquisite mosaic, stone and marble thruout, island kitchen w/dark-stained cherry cabinets, imported granite and wallpaper, custom flooring/tiles. State-of-the-art Master BA w/Grohe fixtures, rain and steam w/multiple shower... View all property information
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5 of 5 stars Reviewed January 27, 2015
I rented this town home for a girls gathering before my sister got married 2 weeks later. I turned out to phenomenal!!!! The owner was flexible and cooperative, the house was...
3 of 5 stars Reviewed September 17, 2014
Nice place, only one bed and couldn't use the garage as advertised. Parking is a bit tricky, had to park several blocks away on Hubbard, but when rush hour ends it is good. No...
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From
$395
Per Night
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1 / 34
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Lincoln Square
5 Bedrooms, 5 Bathrooms, Sleeps 12
Bookings
Details Make Inquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Fireplace
  • Hot Tub
  • Internet Access
  • Satellite TV
Suitability
  • 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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From
$150
Per Night
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1 / 14
Payment Protection
2 Bedrooms, 2 Bathrooms, Sleeps 10
Details Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Housekeeping...
  • Housekeeping...
  • Internet Access
  • Safe
  • Satellite TV
  • Wi-Fi
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • Wheelchair access
  • Elder access
  • x
  • x
About this property
Modern 3BD 2Bth Brick-Style Ranch! Sleeps 10!! ASK ABOUT OUR PRICE MATCHING OPTION!! Very affordable home in west suburb that offers easy access to the city. Sleeps up to 10 people. -3 Bedrooms -2 Bathroom -Hardwood Floors -Tiled Bathroom -Centrally controlled Heat and Air -Big back yard... View all property information
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From
$199
Per Night
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1 / 13
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Northwest Side
4 Bedrooms, 4 Bathrooms, Sleeps 10
Bookings
Details Make Inquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Hot Tub
  • Internet Access
  • Sauna
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • Wheelchair access
  • Elder access
  • x
  • ?
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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From
$225
Per Night
View Details
1 / 9
Payment Protection
3 Bedrooms, 1 Bathroom, Sleeps 5
Details Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
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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From
$550
Per Night
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1 / 13
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Northwest Side
4 Bedrooms, 2 Bathrooms, Sleeps 10
Details Make Inquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Available ONLY 12/23/14- 12/29/14 We normally take 2 long vacations and are willing to rent our place. This house is fully furnished with a fully operational kitchen and full use of cooking utensils. Seating for up to 10 at dining room table. This house is best for someone looking to get their... View all property information
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From
$265
Per Night
View Details
1 / 9
Payment Protection
3 Bedrooms, 1 Bathroom, Sleeps 6
Booking
Details Reviews (1) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
  • ?
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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From
$265
Per Night
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1 / 10
Payment Protection
3 Bedrooms, 1 Bathroom, Sleeps 5
Details Reviews (1) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Internet Access
  • Safe
  • Satellite TV
  • Washer
  • Wi-Fi
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Just 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. Comfy & inviting. Private entrance, private deck, plenty of space in this 3 bedroom unit. Updated kitchen, stainless Maytag appliances (built-in... View all property information
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5 of 5 stars Reviewed August 4, 2014
We had a wonderful stay on Belle Plaine Ave. Victoria was very accommodating to our needs and the apartment is beautiful. The neighborhood is also great, quiet but with walking...
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From
$487
Per Night
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1 / 15
Payment Protection
3 Bedrooms, 1 Bathroom, Sleeps 6
Details Reviews (15) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Fireplace
  • Grill
  • Hot Tub
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Book Now for ALL INCLUSIVE BUDGET PACKAGE at a unique and beautifully decorated Bed & Breakfast inn. Stay on our third floor apartment with a shared bath and accommodations for up to 6-9 travelers - Full Size Refrigerator, Huge Leather Couch, Dinette Set, Massage Chair, Air Hockey Table and so... View all property information
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5 of 5 stars Reviewed April 13, 2013
We were visiting Chicago for accepted students' visit days at University of Chicago and wanted to stay somewhere close to the university that wasn't a Ramada Inn type hotel...
4 of 5 stars Reviewed December 7, 2012
We enjoyed our stay at Welcome Inn Manor B and B. Mel and his assistant were very hospitable, and always started our day off with a hearty and tasty breakfast. Mel is at the ready...
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From
$90
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1 / 12
Lincoln Park
2 Bedrooms, 2 Bathrooms, Sleeps 6
Details Reviews (6) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Fireplace
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
This is a home we like to come back to so we have furnished and decorated for luxury and comfort. It’s impeccably clean with modern décor & luxury linens: *600 thread-count linens *Plush towels *Marble & Slate flooring in bathrooms *Italian tile in bathrooms *Spa bath It is located in Old Town- a... View all property information
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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.