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
Guest suite in Chicago
4.98 out of 5 average rating, 111 reviewsGorgeous Studio 15 Minutes From Ohare!
21–28 Oct
$209 NZD per night
Guest favourite
Guesthouse in Edgewater
4.95 out of 5 average rating, 367 reviewsCozy Coach House
19–26 Aug
$244 NZD per night
Guest favourite
Guest suite in Chicago
4.96 out of 5 average rating, 320 reviewsGorgeous, cozy 1-bedroom Suite in Andersonville
27 Apr – 4 May
$184 NZD per night
Superhost
Apartment in Chicago
4.81 out of 5 average rating, 124 reviewsTranquil & Airy 1BR Apt in Lincoln Square
7–14 May
$247 NZD per night
Guest favourite
Apartment in Chicago
4.97 out of 5 average rating, 251 reviewsSpacious 1BR apartment in a central location
30 Sep – 7 Oct
$213 NZD per night
Guest favourite
Apartment in Roscoe Village
4.96 out of 5 average rating, 238 reviewsRoscoe Village One Bed Lux Apartment Near Wrigley
2–9 Dec
$238 NZD per night
Guest favourite
Apartment in Oak Park
4.85 out of 5 average rating, 531 reviewsLong stays welcome@warm&cute vintage 2BR
20–27 Oct
$197 NZD per night
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
29 Sep – 6 Oct
$252 NZD per night
Quick stats about holiday rentals 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 Holiday rentals
- Lake Michigan Beach Holiday rentals
- Saugatuck Holiday rentals
- Evanston Holiday rentals
- Holland Holiday rentals
- South Haven Holiday rentals
- Naperville Holiday rentals
- South Side Holiday rentals
- South Bend Holiday rentals
- New Buffalo Holiday rentals
- Rentals with a balcony Chicago
- Rentals with a washing machine and dryer Chicago
- Monthly Rentals Chicago
- Townhouse rentals Chicago
- Rentals with a fireplace Chicago
- Rentals with a patio Chicago
- Rentals with an accessible height bed Chicago
- Rentals with a sauna Chicago
- Rentals with a hot tub Chicago
- Rentals with breakfast Chicago
- Boutique hotel rentals Chicago
- Rentals with an EV charger Chicago
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- Rentals with pools Chicago
- Smoking-friendly rentals Chicago
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- Loft rentals Chicago
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- Apartment rentals Chicago
- Lakehouse rentals Chicago
- Hotel rentals Chicago
- Rentals with lake access Chicago
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- Bed and breakfasts Chicago
- Condo rentals Chicago
- Rentals with a home theatre Chicago
- Yurt Rentals United States
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