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Vacation Rentals in Chicago, IL

Professionally managed typically means…
  • Dedicated on-site help
  • Experienced local staff
  • Professional hospitality services
  • Secure credit card payment
Verified property owner typically means…
  • Enhanced property ownership verification in addition to verification of owner name and address via valid credit card
  • Established history of renting online
  • Direct & personal contact
  • Detailed rental knowledge
  • Flexible dates & rates
  • More options in smaller towns
Property owner typically means…
  • Verification of owner name and address via valid credit card
  • Direct & personal contact
  • Detailed rental knowledge
  • Flexible dates & rates
  • More options in smaller towns
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All 182 Rentals in Chicago
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From
$159
Per Night
Near North Side
Studio, 1 Bathroom, Sleeps 2
8 photos Details
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From
$200
Per Night
The Loop
1 Bedroom, 1 Bathroom, Sleeps 4
32 photos Details
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From
$287
Per Night
Lakeview
3 Bedrooms, 1 Bathroom, Sleeps 6
26 photos Details
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Also consider
Family & Group Accommodations on 3rd Floor Apartment in Historic Home
3 Bedrooms, sleeps 6
$459 / night
2Bedroom in ICONIC BUILDING Next 2 W Hotel by Lake
2 Bedrooms, sleeps 5
$350 / night
Beautiful Lincoln Park House
6 Bedrooms, sleeps 14
$11,000 / month
Penthouse At The Lex...massive Skyline Views!!
2 Bedrooms, sleeps 6
$300 / night
From
$400
Per Night
Near North Side
1 Bedroom, 1 Bathroom, Sleeps 3
13 photos Details
Make Inquiry
From
$625
Per Night
Near North Side
3 Bedrooms, 2 Bathrooms, Sleeps 8
12 photos Details
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From
$250
Per Night
Near North Side
1 Bedroom, 1 Bathroom, Sleeps 1
28 photos Details
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From
$250
Per Night
Roscoe Village
4 Bedrooms, 2 Bathrooms, Sleeps 10
4 photos Details
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From
$311
Per Night
Lakeview
3 Bedrooms, 2 Bathrooms, Sleeps 6
25 photos Details
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Get the List
From
$599
Per Night
Near North Side
2 Bedrooms, 2 Bathrooms, Sleeps 7
12 photos Details
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From
$245
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
9 photos Details
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From
$175
Per Night
2 Bedrooms, 1 Bathroom, Sleeps 3
6 photos Details
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From
$160
Per Night
Gold Coast, Near North Side
Studio, 1 Bathroom, Sleeps 2
7 photos Details
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From
$265
Per Night
3 Bedrooms, 1 Bathroom, Sleeps 5
10 photos Details
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From
$225
Per Night
Roscoe Village
2 Bedrooms, 2 Bathrooms, Sleeps 6
8 photos Details
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From
$550
Per Night
Near North Side
2 Bedrooms, 2 Bathrooms, Sleeps 7
19 photos Details
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From
$260
Per Night
Near North Side
1 Bedroom, 1 Bathroom, Sleeps 4
10 photos Details
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From
$234
Per Night
The Loop
2 Bedrooms, 2 Bathrooms, Sleeps 6
13 photos Details
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From
$130
Per Night
Northwest Side
2 Bedrooms, 2 Bathrooms, Sleeps 4
2 photos Details
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From
$139
Per Night
The Loop
1 Bedroom, 1 Bathroom, Sleeps 2
7 photos Details
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From
$229
Per Night
Roscoe Village
2 Bedrooms, 1 Bathroom, Sleeps 6
11 photos Details
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From
$139
Per Night
Northwest Side, Wicker Park / Bucktown
1 Bedroom, 1 Bathroom, Sleeps 2
3 photos Details
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From
$180
Per Night
Lakeview
1 Bedroom, 1 Bathroom, Sleeps 3
8 photos Details
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From
$249
Per Night
Roscoe Village
2 Bedrooms, 1 Bathroom, Sleeps 6
16 photos Details
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From
$119
Per Night
West Town
1 Bedroom, 1 Bathroom, Sleeps 4
11 photos Details
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From
$150
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
9 photos Details
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From
$1,277
Per Night
Lakeview
11 Bedrooms, 6 Bathrooms, Sleeps 21
49 photos Details
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Neighborhood

  • All (182)
  • DePaul (9)
  • East Side (0)
  • Gold Coast (13)
  • Hyde Park (0)
  • Lakeview (16)
  • Lincoln Park (2)
  • Lincoln Square (0)
  • Near North Side (56)
  • Near South Side (0)
  • Northwest Side (16)
  • O'Hare (0)
  • Pilsen (0)
  • Rogers Park (5)
  • Roscoe Village (7)
  • Southwest Side (3)
  • The Loop (32)
  • University Village / Little Italy (0)
  • West Town (6)
  • Wicker Park / Bucktown (3)
Learn about Chicago neighborhoods

Suitability

  • Wheelchair access (65)
  • Elder access (107)
  • Suitable for children (121)
  • Pet friendly (53)
  • Smoking allowed (0)

Amenities

  • Air Conditioning (118)
  • Internet (117)
  • Other outdoor space (90)
  • Washer/Dryer (76)
  • Parking (65)
  • View all amenities
Filter search results by:
Book Online(152)

Neighborhood

  • All (182)
  • DePaul (9)
  • East Side (0)
  • Gold Coast (13)
  • Hyde Park (0)
  • Lakeview (16)
  • Lincoln Park (2)
  • Lincoln Square (0)
  • Near North Side (56)
  • Near South Side (0)
  • Northwest Side (16)
  • O'Hare (0)
  • Pilsen (0)
  • Rogers Park (5)
  • Roscoe Village (7)
  • Southwest Side (3)
  • The Loop (32)
  • University Village / Little Italy (0)
  • West Town (6)
  • Wicker Park / Bucktown (3)
Learn about Chicago neighborhoods

Suitability

  • Wheelchair access (65)
  • Elder access (107)
  • Suitable for children (121)
  • Pet friendly (53)
  • Smoking allowed (0)

Amenities

  • Air Conditioning (118)
  • Internet (117)
  • Other outdoor space (90)
  • Washer/Dryer (76)
  • Parking (65)
  • 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.