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Weekend Getaways in Chicago - Vacation Rentals

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All 199 Rentals in Chicago
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From
$575
Per Night
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1 / 23
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3 Bedrooms, 2 Bathrooms, Sleeps 10
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From
$165
Per Night
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1 / 6
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1 Bedroom, 1 Bathroom, Sleeps 4
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From
$225
Per Night
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1 / 9
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2 Bedrooms, 1 Bathroom, Sleeps 6
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From
$300
Per Night
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1 / 14
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2 Bedrooms, 1 Bathroom, Sleeps 4
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Amenities & Details
  • Air Conditioning
  • Dishwasher
  • 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
Brilliantly sunny top floor of historic two flat on a lovely tree lined street. The well appointed apartment is beautiful. It has been furnished very thoughtfully, with comfort and simplicity in mind - It boasts of old world charm along with modern conveniences. Steps away from the quaint... View all property information
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From
$150
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1 / 27
3 Bedrooms, 1 Bathroom, Sleeps 5
Details Reviews (11) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Internet Access
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Located on the north side of the city near the lake, redline train, 15 minutes to downtown and northshore. Condo has central heat and air and offers 1200 square feet of living space with separate living room and dining room, your own balcony, and bedrooms with tasteful linens, ultra comfortable... View all property information
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From
$623
Per Week
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1 / 40
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The Loop
Studio, 1 Bathroom, Sleeps 2
Bookings
Details Reviews (6) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Gym
  • Internet Access
  • Satellite TV
  • Shared Outdoor Pool...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • Wheelchair access
  • Elder access
About this property
888.761.RENT or 312.242.1625 215 W. Washington St. Chicago, IL. 60606 (Washington/Wells in the Loop in Downtown Chicago - Five Blocks West of Michigan Avenue and Millenium Park 'Bean'; In Business/Theater District) Check Availability and Book Online Now: http://reservation.worldweb.com/hotel/1278... View all property information
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From
$4,100
Per Month
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1 / 19
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Near North Side
1 Bedroom, 1 Bathroom, Sleeps 1
Booking
Details Reviews (1) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Gym
  • Hot Tub
  • Satellite TV
  • Sauna
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
About this property
Optima is a new building opening in Spring of 2013, towering 42 stories over Michigan Avenue. Sleek design incorporates floor-to-ceiling reflective glass windows and European-designed finishes throughout. The condo features 700 sq. ft. of bamboo flooring, porcelain tile, granite counter tops,... 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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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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From
$90
Per Night
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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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From
$299
Per Night
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1 / 34
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The Loop
2 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
Details Reviews (1) 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
Welcome to Chicago -- far from your typical Chicago rental. The building offers unparalleled amenities, upscale stylish accommodations, and floor-to-ceiling dynamic views of the Chicago skyline. This property is unlike any other in its class and the experience is definitely one-of-a-kind.... View all property information
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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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From
$200
Per Night
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1 / 10
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The Loop
1 Bedroom, 1 Bathroom, Sleeps 4
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Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
About this property
This is another one of our properties in the South Loop that has amazing amenities and a great feel to it. You will see from the pictures there is a king sized bed along with a sleeper sofa in the loving room which is how this unit can accommodate four people. Please let me know what questions you... View all property information
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From
$140
Per Night
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1 / 15
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Northwest Side
3 Bedrooms, 1 Bathroom, Sleeps 6
Bookings
Details Make Inquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
We created this new construction apartment to fit our family as a second home. We live in Arkansas but are from Chicago with friends and family all here. When we visit it is perfect for our family of 5 with a crib, bunk bed, and queen bed. A twin blow up air mattress can be available upon... View all property information
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From
$167
Per Night
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1 / 9
1 Bedroom, 1 Bathroom, Sleeps 4
Details Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Internet Access
  • Satellite TV
  • Washer
  • Waterfront
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Are you planning a trip to Chicago? Why stay in an expensive hotel room when you can rent furnished luxury condos, some with PENTHOUSE views of downtown Chicago and the lake. We stay in the apartments so they are stocked with most anything you would need to cook and entertain with. Condos have full... View all property information
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From
$299
Per Night
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1 / 30
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Near North Side
1 Bedroom, 1 Bathroom, Sleeps 1
Details Make Inquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Grill
  • Gym
  • Hot Tub
  • Internet Access
  • Pool Table
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
About this property
Pet: Pet Friendly AVAILABLE JANUARY 29TH!!!!!!!!!!!! Features: 100 sq. ft balcony, grill and patio furniture Newly furnished condo from Room and Board. New appliances Includes new linens, towels All kitchen appliances/table wear/pots and pans 55' LED LCD TV with DVD SURROUND... View all property information
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From
$249
Per Night
View Details
1 / 13
Payment Protection
1 Bedroom, 1 Bathroom, Sleeps 4
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Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Enjoy resort style living in the Alta apartments in the the cozy and modern River West neighborhood. Unit boasts incredible river views and all the modern amenities of a new building. View all property information
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From
$150
Per Night
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1 / 28
Payment Protection
Near North Side
1 Bedroom, 1 Bathroom, Sleeps 4
Details Make Inquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • Wheelchair access
  • Elder access
About this property
Welcome to Optima Chicago. This building just opened in August of 2013 and has the amenities everyone wants. Indoor pool, rooftop hot tub, indoor basketball court, and more! Your stay here will be nothing short of amazing and you will want to return! View all property information
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From
$4,700
Per Month
View Details
1 / 31
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Near North Side
1 Bedroom, 1 Bathroom, Sleeps 4
Details Make Inquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • Wheelchair access
  • Elder access
About this property
Welcome to Optima Chicago. This building just opened in August of 2013 and has the amenities everyone wants. Indoor pool, rooftop hot tub, indoor basketball court, and more! Your stay here will be nothing short of amazing and you will want to return! View all property information
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From
$150
Per Night
View Details
1 / 10
Gold Coast, Near North Side
1 Bedroom, 1 Bathroom, Sleeps 3
Details Make Inquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Hot Tub
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Located in the heart of Chicago, these Corporate Furnished Apartments offer breathtaking views, rooftop deck with poolside service, premier gym, wireless internet lounge, and much more. Overlooking 1,200 acres of glorious Lincoln Park greenery and offering panoramic views of Lake Michigan, our... View all property information
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From
$5,900
Per Month
View Details
1 / 33
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Gold Coast, Near North Side
2 Bedrooms, 2 Bathrooms, Sleeps 6
Booking
Details Make Inquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • Wheelchair access
  • Elder access
About this property
There's a new face on an architectural gem in downtown Chicago and it's Axis Apartments & Lofts. Wrapped in striking lake & city views, this modern high-rise conceals two exceptional living space options within. Live your life from a heightened perspective. Live your life at Axis.... View all property information
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From
$2,200
Per Week
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1 / 22
Payment Protection
Near North Side
2 Bedrooms, 2 Bathrooms, Sleeps 6
Details Make Inquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
This is a beautiful high end building and modernly furnished condo in the heart of River North that can accommodate up to six people. 2 bedrooms with queen sized beds and 2 bathrooms, plus a huge sectional couch with a fully equipped kitchen. View all property information
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From
$6,600
Per Month
View Details
1 / 21
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The Loop
2 Bedrooms, 2 Bathrooms, Sleeps 5
Details Make Inquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Gym
  • Internet Access
  • Pool Table
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • Wheelchair access
  • Elder access
About this property
This building just opened up in July of 2014 and is the most modern building you can find in the Chicago Loop area. From the state of the art amenities to the amazing and helpful staff, you will love staying at this apartment. Located in the Loop you have access to all the tourist attractions as... View all property information
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From
$300
Per Night
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1 / 35
Payment Protection
The Loop
2 Bedrooms, 2 Bathrooms, Sleeps 5
Details Make Inquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Stay in luxury at this awesome penthouse unit in the South Loop of Chicago. Beautiful Lake views and a spacious 2 bedroom 2 bathroom apartment in the award winning Lex building. Chinatown and downtown are just a stone's throw away when you stay at this apartment. View all property information
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From
$200
Per Night
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1 / 22
Lakeview
2 Bedrooms, 1 Bathroom, Sleeps 4
Details Make Inquiry
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
$299
Per Night
View Details
1 / 44
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The Loop
1 Bedroom, 1 Bathroom, Sleeps 4
Details Make Inquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Experience high rise living in a state of the art building that has just opened up this summer of 2014. This building has everything you could ever want from a brand new high rise off Wacker Drive in Chicago. Location is ideal for anything that you are looking to experience in the city. View all property information
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From
$6,200
Per Month
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1 / 41
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Near North Side
2 Bedrooms, 2 Bathrooms, Sleeps 6
Booking
Details Make Inquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
OPTIMA CITY CENTER THIS IS A NEW UPSCALE BUILDING IN STREETERVILLE AWARD WINNING ARCHITECT, BUILDING IS ULTRA CONTEMPORARY WITH FIRST CLASS VIEWS AND AMENITIES. ALL UTILITIES INCLUDED, CONDO QUALITY FINISHES, IN UNIT W/D. WE CAN DO ANY LEASE LENGTH PRICES SUBJECT TO AVALIBILTY View all property information
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From
$197
Per Night
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1 / 7
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Northwest Side
2 Bedrooms, 2 Bathrooms, Sleeps 8
Booking
Details Reviews (1) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Hot Tub
  • Internet Access
  • Safe
  • Satellite TV
  • Washer
Suitability
  • 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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From
$100
Per Night
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1 / 14
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Rogers Park
3 Bedrooms, 1 Bathroom, Sleeps 8
Bookings
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Internet Access
Suitability
  • 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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From
$130
Per Night
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1 / 12
Payment Protection
1 Bedroom, 1 Bathroom, Sleeps 2
Details Reviews (7) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Internet Access
  • Satellite TV
  • Washer
  • Waterfront
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Elegant 1 and 2 bedroom apartments on N Lake Shore Drive,10 min away from Michigan Avenue, Northwestern Memorial Hospital, 25 min by bus to Millenium Park and the Art Institute. Fully furnished, beautiful oak floors, high ceilings, custom architectural details.Perfect residential accommodations for... View all property information
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From
$100
Per Night
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1 / 20
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Rogers Park
3 Bedrooms, 1 Bathroom, Sleeps 8
Bookings
Details Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Internet Access
Suitability
  • 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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From
$167
Per Night
View Details
1 / 13
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Northwest Side
2 Bedrooms, 1 Bathroom, Sleeps 4
Bookings
Details Make Inquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Internet Access
  • Satellite TV
Suitability
  • 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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From
$100
Per Night
View Details
1 / 18
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Rogers Park
2 Bedrooms, 2 Bathrooms, Sleeps 4
Bookings
Details Make Inquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
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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From
$275
Per Night
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1 / 14
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The Loop
2 Bedrooms, 2 Bathrooms, Sleeps 5
Bookings
Details Reviews (1) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Grill
  • Gym
  • Hot Tub
  • Internet Access
  • Private Outdoor...
  • Safe
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
About this property
The Tides is a great way to experience life and culture in the heart of Chicago! Featuring a modern contemporary feel, the short term rentals at The Tides offer dramatic finishes including tiled entries, granite islands and cherry cabinetry, open floor plans with captivating views from the... View all property information
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From
$1,022
Per Night
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1 / 49
Lakeview
11 Bedrooms, 6 Bathrooms, Sleeps 21
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Looking for Space? You've Come to the Right Place! The Lakewood Avenue property has three apartments in the building offering plenty of space for your larger gathering while at the same time providing some privacy when you need those 'alone' times! 10 Bedrooms (13 beds) & 6 Bathrooms total--Sleeps... View all property information
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From
$205
Per Night
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1 / 12
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Gold Coast, Near North Side
1 Bedroom, 1 Bathroom, Sleeps 4
Bookings
Details Reviews (2) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Fireplace
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Enjoy this fabulous Chicago brownstone vacation rental located in the heart of the exclusive Gold Coast neighborhood. This downtown vacation rental gives you access to all the amazing features of downtown Chicago. Enjoy the shopping, eateries and entertainment that you can only find here. A... View all property information
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From
$205
Per Night
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1 / 12
Payment Protection
Gold Coast, Near North Side
1 Bedroom, 1 Bathroom, Sleeps 4
Details Reviews (1) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Fireplace
  • Internet Access
  • Satellite TV
  • Waterfront
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
First Class Chicago vacation rentals by owner gives you the loveliest choice in Chicago Brownstone vacation rentals. Located in the Gold Coast neighborhood, these brownstones will surpass your expectations for quality and comfort. You will never want for a Magnificent Mile hotel as First Class... View all property information
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From
$199
Per Night
View Details
1 / 9
Payment Protection
Near North Side
1 Bedroom, 1 Bathroom, Sleeps 2
Bookings
Details Reviews (1) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Fireplace
  • Internet Access
  • Safe
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Experience our 1 bedroom fully furnished “Old Town Chicago” condos designed by famous Chicago artist Edgar Miller (The Chicago Renaissance Man) with Flat Panel HDTVs, Fireplaces, All Utilities, All Major Appliances, WiFi, Internet, Cable, Queen Size Tempur-Pedic Mattresses, Cleaning Service... View all property information
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From
$199
Per Night
View Details
1 / 15
Payment Protection
Near North Side
1 Bedroom, 1 Bathroom, Sleeps 2
Booking
Details Reviews (1) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Fireplace
  • Internet Access
  • Safe
  • Satellite TV
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Experience our 1 bedroom fully furnished “Old Town Chicago” condos designed by famous Chicago artist Edgar Miller (The Chicago Renaissance Man) with Flat Panel HDTVs, Fireplaces, All Utilities, All Major Appliances, WiFi, Internet, Cable, Queen Size Tempur-Pedic Mattresses, Cleaning Service... View all property information
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From
$500
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1 / 24
The Loop
2 Bedrooms, 2 Bathrooms, Sleeps 6
Booking
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Amenities & Details
  • Air Conditioning
  • Internet Access
  • Satellite TV
  • Washer
  • Waterfront
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • x
About this property
Beautiful B & B Boatel Yacht - Pier Gold offers Chicago visitors a great alternative to regular hotel stays. Located at Chicago's most sought after harbor in the heart of our city waterfront; at Burnham Harbor you will enjoy waking up at your floating waterfront boatel at our harbor with stunning... View all property information
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$305
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1 / 12
Payment Protection
Gold Coast, Near North Side
2 Bedrooms, 2 Bathrooms, Sleeps 8
Bookings
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Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Fireplace
  • Internet Access
  • Satellite TV
  • Waterfront
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Apartment - 2 Bedrooms + Convertible bed(s) - 2 Baths - (Sleeps 4-8) Another First Class Chicago property! City of Chicago Vacation Rental License #2125365. Rent Legally! You've found it! Location, Location, Location! An historic 1890's brownstone in the heart of the exclusive Gold Coast where... View all property information
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From
$299
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1 / 11
Payment Protection
Near North Side
3 Bedrooms, 1 Bathroom, Sleeps 6
Booking
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Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Included is a 3-bedroom fully furnished “Old Town Chicago” condo with TWO PRIVATE BALCONIES, Flat Panel HDTVs, Fireplaces, All Utilities, All Major Appliances, WiFi, Internet, Cable, Queen Size Mattresses, Cleaning Service upon Vacating Included, Complimentary Laundry, and all of the atmosphere... View all property information
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From
$159
Per Night
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1 / 7
Payment Protection
Near North Side
Studio, 1 Bathroom, Sleeps 2
Bookings
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Fireplace
  • Internet Access
  • Safe
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • Wheelchair access
  • Elder access
  • x
About this property
Experience our amazing, over sized, fully furnished “Old Town Chicago” studio with private balcony designed by famous Chicago artist Edgar Miller (The Chicago Renaissance Man) with Flat Panel HDTVs, Fireplaces, All Utilities, All Major Appliances, WiFi, Internet, Cable, Queen Size Tempur-Pedic... View all property information
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From
$249
Per Night
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1 / 17
Payment Protection
Near North Side
2 Bedrooms, 1 Bathroom, Sleeps 4
Bookings
Details Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Fireplace
  • Internet Access
  • Safe
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • x
About this property
Experience our 2 bedroom fully furnished “Old Town Chicago” condos designed by famous Chicago artist Edgar Miller (The Chicago Renaissance Man) with Flat Panel HDTVs, Fireplaces, All Utilities, All Major Appliances, WiFi, Internet, Cable, Queen Size Mattresses, Cleaning Service Included,... View all property information
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From
$250
Per Night
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1 / 10
The Loop
2 Bedrooms, 2 Bathrooms, Sleeps 6
Details Reviews (5) Make Inquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • x
  • Wheelchair access
  • Elder access
About this property
**LOCATION **LOCATION **LOCATION! ***CAN'T BEAT IT! ***Views Views Views! Breathtaking Lake and City Views!!*** Looks Like Hawaii Up There!*** Set in the heart of Downtown Chicago, our Chicago apt is ideally placed for visitors to experience all that the city has to offer. On the doorstep of... View all property information
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From
$120
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1 / 7
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Lincoln Park
1 Bedroom, 1 Bathroom, Sleeps 3
Bookings
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Amenities & Details
  • Air Conditioning
  • Internet Access
  • Safe
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Wireless Internet Flat Screen TV in bedroom and living room Cable Clean sheets and towels Silverware, pots & pans Very large bedroom and living room Wall unit AC's in bedroom and living room Washer & Dryer is downstairs on first floor This is an ideal location for visitors. Nice restaurants... View all property information
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From
$150
Per Night
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1 / 13
Payment Protection
Near North Side
2 Bedrooms, 1 Bathroom, Sleeps 4
Bookings
Details Reviews (1) Make Inquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Great Old Town 2BR. Very homey and well suited for travelers on business or leisure. Steps away from all public transportation in a area with gorgeous tree lined streets and high end accommodations. The Space Welcome to my 2 bedroom fully furnished “Old Town Chicago” condo. Inside there... View all property information
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From
$999
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1 / 55
Payment Protection
Northwest Side, Wicker Park / Bucktown
3 Bedrooms, 5 Bathrooms, Sleeps 6
Booking
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Hot Tub
  • Internet Access
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • x
About this property
Architecturally significant single family home in Chicago's best neighborhood, Wicker Park. This home has been featured in design magazines and is ideal for entertaining. Filled with mid-mod furnishings throughout. Forbes rated Wicker Park #4 in the country for hippest neighborhoods, and this home... View all property information
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From
$99
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1 / 4
Payment Protection
Near North Side
1 Bedroom, 1 Bathroom, Sleeps 3
Details Make Inquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
About this property
Step into this modern loft in the heart of Old Town Corridor only steps from the Brown Line- Sedgwick Stop and all Wells Street has to offer. Hardwood floors throughout with a lofted bedroom overlooking the unit. View all property information
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From
$315
Per Night
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1 / 32
The Loop
3 Bedrooms, 2 Bathrooms, Sleeps 6
Details Reviews (2) Make Inquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
About this property
Take me to the Penthouse! Stay in our Penthouse Condo on the 50th Floor! A true Penthouse, stunning views of the lake and city. Walk to everything downtown. Upgraded everything. Granite kitchen counter tops, stainless steal appliances, marble in the bathrooms, king size beds, floor to ceiling... View all property information
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Book Online(132)

Neighborhood

  • All (199)
  • DePaul (9)
  • East Side (0)
  • Gold Coast (8)
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Learn about Chicago neighborhoods

Suitability

  • Wheelchair access (46)
  • Elder access (96)
  • Suitable for children (35)
  • Pet friendly (39)
  • Smoking allowed (2)

Amenities

  • Air Conditioning (139)
  • Internet (131)
  • Other outdoor space (101)
  • Washer/Dryer (92)
  • Parking (67)
  • View all amenities