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Vacation rentals in Chicago, IL

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All 172 Rentals in Chicago
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From
$274
Per Night
Northwest Side
3 Bedrooms, 2 Bathrooms, Sleeps 8
Bookings
18 photos Details
Reviews (1) Make Enquiry
From
$159
Per Night
1 Bedroom, 1 Bathroom, Sleeps 4
Bookings
28 photos Details
Reviews (2) Make Enquiry
From
$219
Per Night
Northwest Side
2 Bedrooms, 2 Bathrooms, Sleeps 5
Bookings
8 photos Details
Reviews (2) Make Enquiry
Also consider
Wyndham Grand Chicago Riverfront, downtown Chicago
1 Bedroom, sleeps 4
$214 - $283 / night
Furnished short term at the COAST
1 Bedroom, sleeps 3
$147 / night
Luxurious Condo Balcony View and Pool
2 Bedrooms, sleeps 6
$328 / night
Gorgeous 1 Bedroom Unit In Chicago
1 Bedroom, sleeps 4
$296 / night
From
$88
Per Night
Lakeview
1 Bedroom, 1 Bathroom, Sleeps 2
Bookings
6 photos Details
Reviews (2) Make Enquiry
From
$329
Per Night
Near North Side
1 Bedroom, 1 Bathroom, Sleeps 1
Booking
19 photos Details
Reviews (1) Make Enquiry
From
$247
Per Night
Lakeview
2 Bedrooms, 1 Bathroom, Sleeps 5
Bookings
11 photos Details
Reviews (2) Make Enquiry
From
$88
Per Night
Studio, 1 Bathroom, Sleeps 2
Bookings
14 photos Details
Reviews (2) Make Enquiry
From
$274
Per Night
Lakeview
2 Bedrooms, 1 Bathroom, Sleeps 6
Booking
15 photos Details
Reviews (2) Make Enquiry
Get the List
From
$154
Per Night
Gold Coast, Near North Side
Studio, 1 Bathroom, Sleeps 3
Bookings
19 photos Details
Reviews (1) Make Enquiry
From
$218
Per Night
Near North Side
1 Bedroom, 1 Bathroom, Sleeps 2
15 photos Details
Reviews (1) Make Enquiry
From
$329
Per Night
The Loop
2 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
27 photos Details
Reviews (3) Make Enquiry
From
$71
Per Night
Northwest Side
1 Bedroom, 1 Bathroom, Sleeps 2
Bookings
14 photos Details
Reviews (8) Make Enquiry
From
$93
Per Night
Northwest Side
2 Bedrooms, 1 Bathroom, Sleeps 4
Bookings
15 photos Details
Reviews (5) Make Enquiry
From
$329
Per Night
Lakeview
3 Bedrooms, 2 Bathrooms, Sleeps 8
Booking
13 photos Details
Reviews (9) Make Enquiry
From
$148
Per Night
Rogers Park
2 Bedrooms, 1 Bathroom, Sleeps 7
Bookings
28 photos Details
Reviews (3) Make Enquiry
From
$165
Per Night
The Loop
Studio, 1 Bathroom, Sleeps 3
Bookings
13 photos Details
Reviews (2) Make Enquiry
From
$110
Per Night
Near North Side
1 Bedroom, 1 Bathroom, Sleeps 1
Bookings
22 photos Details
Reviews (4) Make Enquiry
From
$163
Per Night
3 Bedrooms, 1 Bathroom, Sleeps 8
Bookings
10 photos Details
Reviews (2) Make Enquiry
From
$120
Per Night
1 Bedroom, 1 Bathroom, Sleeps 6
Bookings
20 photos Details
Reviews (3) Make Enquiry
From
$132
Per Night
Gold Coast, Near North Side
Studio, 1 Bathroom, Sleeps 2
Bookings
26 photos Details
Reviews (4) Make Enquiry
From
$384
Per Night
Lakeview
2 Bedrooms, 1 Bathroom, Sleeps 6
Bookings
13 photos Details
Reviews (14) Make Enquiry
From
$152
Per Night
3 Bedrooms, 1 Bathroom, Sleeps 8
Bookings
14 photos Details
Reviews (2) Make Enquiry
From
$98
Per Night
Northwest Side
1 Bedroom, 1 Bathroom, Sleeps 2
Bookings
7 photos Details
Reviews (1) Make Enquiry
From
$216
Per Night
Northwest Side
2 Bedrooms, 2 Bathrooms, Sleeps 8
Booking
7 photos Details
Reviews (1) Make Enquiry
From
$2,929
Per Month
The Loop
Studio, 1 Bathroom, Sleeps 2
Bookings
40 photos Details
Reviews (5) Make Enquiry
From
$165
Per Night
DePaul
1 Bedroom, 1 Bathroom, Sleeps 3
Bookings
14 photos Details
Reviews (1) Make Enquiry
From
$181
Per Night
DePaul
2 Bedrooms, 1 Bathroom, Sleeps 4
Bookings
14 photos Details
Reviews (2) Make Enquiry
From
$192
Per Night
Southwest Side
2 Bedrooms, 2 Bathrooms, Sleeps 6
Booking
48 photos Details
Reviews (13) Make Enquiry
From
$219
Per Night
DePaul
2 Bedrooms, 1 Bathroom, Sleeps 6
Bookings
11 photos Details
Reviews (2) Make Enquiry
From
$548
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 8
Bookings
26 photos Details
Reviews (16) Make Enquiry
From
$148
Per Night
Near North Side
2 Bedrooms, 2 Bathrooms, Sleeps 5
Bookings
37 photos Details
Reviews (5) Make Enquiry
From
$93
Per Night
Northwest Side
1 Bedroom, 1 Bathroom, Sleeps 2
Bookings
16 photos Details
Reviews (26) Make Enquiry
From
$356
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 8
Bookings
23 photos Details
Reviews (12) Make Enquiry
From
$137
Per Night
DePaul
2 Bedrooms, 1 Bathroom, Sleeps 6
Bookings
16 photos Details
Reviews (1) Make Enquiry
From
$274
Per Night
Northwest Side
3 Bedrooms, 2 Bathrooms, Sleeps 8
Bookings
20 photos Details
Reviews (11) Make Enquiry
From
$165
Per Night
DePaul
4 Bedrooms, 1 Bathroom, Sleeps 9
Bookings
17 photos Details
Reviews (5) Make Enquiry
From
$99
Per Night
1 Bedroom, 1 Bathroom, Sleeps 2
Bookings
6 photos Details
Reviews (2) Make Enquiry
From
$274
Per Night
West Town
3 Bedrooms, 2 Bathrooms, Sleeps 5
Bookings
14 photos Details
Reviews (2) Make Enquiry
From
$335
Per Night
Gold Coast, Near North Side
2 Bedrooms, 2 Bathrooms, Sleeps 8
Bookings
12 photos Details
Reviews (6) Make Enquiry
From
$126
Per Night
Northwest Side, Wicker Park / Bucktown
2 Bedrooms, 1 Bathroom, Sleeps 4
Bookings
23 photos Details
Reviews (3) Make Enquiry
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Neighbourhood

  • All (172)
  • DePaul (10)
  • East Side (0)
  • Gold Coast (11)
  • Hyde Park (0)
  • Lakeview (21)
  • Lincoln Park (1)
  • Lincoln Square (1)
  • Near North Side (39)
  • Near South Side (0)
  • Northwest Side (23)
  • O'Hare (0)
  • Pilsen (1)
  • Rogers Park (6)
  • Roscoe Village (8)
  • Southwest Side (2)
  • The Loop (25)
  • University Village / Little Italy (0)
  • West Town (3)
  • Wicker Park / Bucktown (3)
Learn about Chicago neighbourhoods

Suitability

  • Wheelchair access (39)
  • Elder access (77)
  • Suitable for children (92)
  • Pet friendly (35)
  • Smoking allowed (0)

Amenities

  • Air Conditioning (127)
  • Internet (121)
  • Other outdoor space (91)
  • Washer/Dryer (80)
  • Parking (58)
  • View all amenities
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.