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Chicago Vacation Rentals

Find the best deals on 1,118 vacation rentals in Chicago

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Top rentals in Chicago

Find the perfect Chicago vacation rental for your needs
Pittsfield Apartments + Suites
Pittsfield Apartments + Suites
6.6
$91
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Saloon 73
Saloon 73
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Loop Suites
Loop Suites
6.8
$80
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Kasa Chicago South Loop Apartments
Kasa Chicago South Loop Apartments
8.0
$177
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Sonder - The Plymouth
Sonder - The Plymouth
8.0
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Oakwood 200 Squared
Oakwood 200 Squared
9.1
$116
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Stay Alfred At The Seneca
Stay Alfred At The Seneca
$145
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Grand Plaza
Grand Plaza
$167
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Stay Alfred at The Ace on Ashland
Stay Alfred at The Ace on Ashland
$114
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Room in Condo near Univ of Chicago
Room in Condo near Univ of Chicago
5.0
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Dch 215 Lake
Dch 215 Lake
7.0
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River North Waterside Condos
River North Waterside Condos
$144
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Highly Rated Private One Bedroom Apartment: A+ Bucktown/Wicker Park Location
Highly Rated Private One Bedroom Apartment: A+ Bucktown/Wicker Park Location
$192
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A Duplex for your Grouplex
A Duplex for your Grouplex
$135
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Lasalle Lodge
Lasalle Lodge
5.0
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Pilsen Roadhouse
Pilsen Roadhouse
8.0
$119
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Wrigleyville Private Guesthouse
Wrigleyville Private Guesthouse
10.0
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Homan Square
Homan Square
5.0
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Awesome Artsy 1 Bdr Loft Near Park & Train
Awesome Artsy 1 Bdr Loft Near Park & Train
7.3
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Bucktown, Urban Luxury And Convenience. 2 Minutes To L Train Stop At Western
Bucktown, Urban Luxury And Convenience. 2 Minutes To L Train Stop At Western
9.1
$306
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4 bedroom 2 bath perfect for Mccormick place and museum visitors
4 bedroom 2 bath perfect for Mccormick place and museum visitors
$301
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A Beautiful Terraced Artist Duplex Loft Chic Space
A Beautiful Terraced Artist Duplex Loft Chic Space
$130
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The Mozart - Contemporary Logan Square 3bdr
The Mozart - Contemporary Logan Square 3bdr
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Stay Alfred at Park Michigan
Stay Alfred at Park Michigan
$137
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Best Deal 2br Apt For Short & Long Term Stay R2
Best Deal 2br Apt For Short & Long Term Stay R2
7.0
$134
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Beautiful Room in Chicago
Beautiful Room in Chicago
7.0
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At 1426
At 1426
8.0
$192
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Furnished Suites in South Loop Chicago
Furnished Suites in South Loop Chicago
$155
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The Penthouse at Grand Plaza
The Penthouse at Grand Plaza
9.0
$355
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Ginosi 747 Apartel
Ginosi 747 Apartel
$75
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Apartment In River North With Balcony
Apartment In River North With Balcony
$159
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Cute place, convenient to everything in the city
Cute place, convenient to everything in the city
8.4
$62
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Celeste Celebrity Suites
Celeste Celebrity Suites
$163
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Sonder - Lincoln Park Zoo
Sonder - Lincoln Park Zoo
9.2
$173
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Colorful And Comfortable 2bdr With Free Parking
Colorful And Comfortable 2bdr With Free Parking
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The Gulfstream-vibrant Studio Heart of Downtown!
The Gulfstream-vibrant Studio Heart of Downtown!
8.0
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Gorgeous 2BR/2BA Apt near Shedd Aquarium by Domio!
Gorgeous 2BR/2BA Apt near Shedd Aquarium by Domio!
1.0
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Luxury 2 Bedroom in the Heart of Chicago
Luxury 2 Bedroom in the Heart of Chicago
10.0
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New Listing! Printer's Row Getaway With A Gym & Grill Area
New Listing! Printer's Row Getaway With A Gym & Grill Area
9.0
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Sunny, Jumbo 2 Bedroom Mega Space. Walk to Train!
Sunny, Jumbo 2 Bedroom Mega Space. Walk to Train!
7.8
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Corporate Suites Network - 845 N State
Corporate Suites Network - 845 N State
$136
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Wrigleyville Unit - 1/2 block from Wrigley Field - sleeps 5
Wrigleyville Unit - 1/2 block from Wrigley Field - sleeps 5
9.7
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Spacious, Amenity Filled Three Bedroom Apartment in Logan Square
Spacious, Amenity Filled Three Bedroom Apartment in Logan Square
10.0
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Massive 3 bedroom Penthouse
Massive 3 bedroom Penthouse
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Large Home W/Massive Yard
Large Home W/Massive Yard
10.0
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Modern Loop Apartments
Modern Loop Apartments
$113
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Spacious&Modern 15min from DT w/free parking
Spacious&Modern 15min from DT w/free parking
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Premier Luxury at the Coast
Premier Luxury at the Coast
$100
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Remodeled 2 Bed/1bath Condo-Walk To United Center
Remodeled 2 Bed/1bath Condo-Walk To United Center
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Handsome Mccormick 3bd-2ba Loft
Handsome Mccormick 3bd-2ba Loft
9.0
$184
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Sonder - Six Points - Incredible 2br
Sonder - Six Points - Incredible 2br
10.0
$196
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A Stunning Apartment By The Navy Pier!
A Stunning Apartment By The Navy Pier!
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Updated, Bright And Spacious Unit Great For Families & Gatherings
Updated, Bright And Spacious Unit Great For Families & Gatherings
10.0
$226
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Huge 4br, 3 Story Townhouse Ideal For Your Group!!
Huge 4br, 3 Story Townhouse Ideal For Your Group!!
$327
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Luxury Apartments at McCormick Place by Cloud9
Luxury Apartments at McCormick Place by Cloud9
$294
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Roscoe Village Inn Guesthouse Walk To Chicago's Wrigley Field
Roscoe Village Inn Guesthouse Walk To Chicago's Wrigley Field
10.0
$162
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Modern 1br Apt In Loop By Domio
Modern 1br Apt In Loop By Domio
9.6
$174
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Bright And Beautiful, 1 bdrm, 1alcove, 2 qwn beds, I bath, hip Logan square!
Bright And Beautiful, 1 bdrm, 1alcove, 2 qwn beds, I bath, hip Logan square!
9.6
$136
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Forrestville Ave Apartment
Forrestville Ave Apartment
7.8
$98
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Sonder - The Western
Sonder - The Western
9.0
$141
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New 2-Level Home Near Wrigley
New 2-Level Home Near Wrigley
$149
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Domio Loop Architectural 3br Penthouse
Domio Loop Architectural 3br Penthouse
8.8
$264
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New! Charming 3BR in Lincoln Park West by Domio
New! Charming 3BR in Lincoln Park West by Domio
$155
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Corporate Suites in the Heart of Magnificent Mile
Corporate Suites in the Heart of Magnificent Mile
$136
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Distinct Lincoln Park Suites by Sonder
Distinct Lincoln Park Suites by Sonder
$135
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Chicago - Living Large in Lincoln Square .02 to EL
Chicago - Living Large in Lincoln Square .02 to EL
9.1
$128
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Recently Gut Rehabbed Unit In One Of Chicago's Trendiest Neighborhoods!
Recently Gut Rehabbed Unit In One Of Chicago's Trendiest Neighborhoods!
9.0
$172
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Convenient Studio | Fun, Food, Coffee, & Wrigley M9
Convenient Studio | Fun, Food, Coffee, & Wrigley M9
4.0
$74
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Comfy Apt,15min Uber To Cubs Convention, Wrigley M7
Comfy Apt,15min Uber To Cubs Convention, Wrigley M7
9.0
$71
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Chic & Prestine 1br Perfect For Couple Long Stay Mg1
Chic & Prestine 1br Perfect For Couple Long Stay Mg1
8.0
$85
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Abode
Abode
$155
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Andersonvillevr
Andersonvillevr
9.9
$279
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Chic Horner Park Sandstone
Chic Horner Park Sandstone
8.0
$170
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When to book a vacation apartment in Chicago

Check out the tips below to find the best deal on a Chicago vacation rental property
Low Season
January
High Season
October

cheapest month to stay

56%

expected price decrease

most expensive time to stay

33%

expected price increase

Price
$104 - $343
Highest day of week
Thursday
Cheapest day of week
Monday

av. price over the last two weeks

Average price (weeknight)

$254

av. price over the last two weeks

av. price over the last two weeks

Average price (weekend night)

av. price over the last two weeks

Cheapest vacation rentals in Chicago

Our lowest priced vacation apartments and property rentals for a cheaper way to stay in Chicago
Sonder - The Plymouth
Sonder - The Plymouth
8.0
Wrigleyville Private Guesthouse
Wrigleyville Private Guesthouse
10.0
Room in Condo near Univ of Chicago
Room in Condo near Univ of Chicago
5.0
Homan Square
Homan Square
5.0
Lasalle Lodge
Lasalle Lodge
5.0
Beautiful Room in Chicago
Beautiful Room in Chicago
7.0

Chicago vacation apartments & rental properties FAQ

How long do people typically book vacation apartments for in Chicago?

About 2 nights is the most common choice for those booking vacation apartment rentals in Chicago.

How much does a vacation rental apartment in Chicago cost?

The price of a vacation apartment in Chicago depends on the number of guests, locations and required amenities - for a standard apartment in Chicago you can expect to pay around $201 per night.

When is the best time to book a vacation rental in Chicago?

Chicago vacation rentals are at their cheapest in January. Rental prices can be around 56% lower per night than in the high season.

What’s the best area of Chicago to book a vacation rental in?

When looking for vacation apartments in Chicago, recent bookings have shown Hyde Park and Lincoln Park to be the most popular places to stay, with Logan Square also being increasingly considered.

Start planning your trip to Chicago