Holiday houses in Chicago
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Top-rated holiday rentals in Chicago
Guests agree: these stays are highly rated for location, cleanliness and more.
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Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Chicago holiday rentals
Other great holiday rentals in Chicago
Guest favourite
Apartment in Chicago
4.96 out of 5 average rating, 266 reviewsCozy loft in Chicago's Uptown
20 – 27 Oct
$1,463 AUD total
Guest favourite
Apartment in Chicago
4.96 out of 5 average rating, 323 reviewsBright family-friendly Lincoln Square 2-bed 1-bath
18 – 25 Dec
$1,771 AUD total
Guest favourite
Apartment in Roscoe Village
4.96 out of 5 average rating, 238 reviewsRoscoe Village One Bed Lux Apartment Near Wrigley
19 – 26 Nov
$1,489 AUD total
Guest favourite
Guesthouse in Chicago
4.95 out of 5 average rating, 367 reviewsCozy Coach House
19 – 26 Aug
$1,528 AUD total
Guest favourite
Guest suite in Logan Square
4.97 out of 5 average rating, 226 reviewsPrivate Suite w/ offstreet pkg, at Logan Sq Blu Ln
23 – 30 Sept
$1,612 AUD total
Guest favourite
Apartment in Logan Square
4.93 out of 5 average rating, 207 reviewsCozy Private Coach House
3 – 10 July
$1,964 AUD total
Guest favourite
Home in Chicago
4.89 out of 5 average rating, 332 reviewsPrivate 3rd Floor Apartment
16 – 23 Jan
$1,705 AUD total
Guest favourite
Guesthouse in Andersonville
4.91 out of 5 average rating, 342 reviewsPrivate, Charming, Coach House Loft in Andersonville
7 – 14 Dec
$2,126 AUD total
Quick stats about accommodation in Chicago
Total rentals
10K properties
Rentals with dedicated workspaces
6.6K properties have a dedicated workspace
Rentals with a pool
1.1K properties have a pool
Pet-friendly rentals
3.3K properties allow pets
Family-friendly rentals
4.8K properties are a good fit for families
Total number of reviews
466K reviews
Destinations to explore
- Downtown Chicago Holiday rentals
- Milwaukee Holiday rentals
- Lake Geneva Accommodation & holiday rentals
- Lake Michigan Beach Accommodation & holiday rentals
- Saugatuck Accommodation & holiday rentals
- Evanston Accommodation & holiday rentals
- Holland Accommodation & holiday rentals
- South Haven Holiday rentals
- Naperville Accommodation & holiday rentals
- South Side Accommodation & holiday rentals
- South Bend Accommodation & holiday rentals
- New Buffalo Holiday rentals
- Rentals with a balcony Chicago
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- Yurt Rentals United States
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