Holiday houses in Chicago
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Top-rated holiday rentals in Chicago
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Holiday rentals for every style
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Popular amenities for Chicago holiday rentals
Other great holiday rentals in Chicago
Apartment in Logan Square
4.9 out of 5 average rating, 257 reviewsBright & Lofty Bucktown 1br
18 – 25 Jan
Guesthouse in Chicago
4.95 out of 5 average rating, 367 reviewsCozy Coach House
19 – 26 Aug
Guest suite in Chicago
4.98 out of 5 average rating, 112 reviewsGorgeous Studio 15 Minutes From Ohare!
6 – 13 Apr
Guest suite in Chicago
4.97 out of 5 average rating, 226 reviewsPrivate Suite w/ offstreet pkg, at Logan Sq Blu Ln
1 – 8 Oct
Apartment in Cicero
4.98 out of 5 average rating, 203 reviewsCOZY 2Bdr Apt near MDW, Dwtn, United Ctr, Sox, Hwy
25 Apr – 2 May
Guest suite in Andersonville
4.96 out of 5 average rating, 322 reviewsGorgeous, cozy 1-bedroom Suite in Andersonville
27 Feb – 6 Mar
Apartment in Chicago
4.96 out of 5 average rating, 323 reviewsBright family-friendly Lincoln Square 2-bed 1-bath
10 – 17 Dec
Apartment in Chicago
4.96 out of 5 average rating, 238 reviewsRoscoe Village One Bed Lux Apartment Near Wrigley
31 Dec – 7 Jan
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
- Hotel rentals Chicago
- Kid-friendly rentals Chicago
- Loft rentals Chicago
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- Family-friendly rentals Chicago
- Rentals with a home theatre Chicago
- House rentals Chicago
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- Rentals with a hot tub Chicago
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- Rentals with a washing machine and dryer Chicago
- Rentals with an accessible height bed Chicago
- Guesthouse rentals Chicago
- Private suite rentals Chicago
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- Bed and breakfasts Chicago
- Townhouse rentals Chicago
- Apartment rentals Chicago
- Monthly Rentals Chicago
- Rentals with pools Chicago
- Rentals with an EV charger Chicago
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- Beachfront rentals Chicago
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- Waterfront rentals Chicago
- Lakehouse rentals Chicago
- Condo rentals Chicago
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- Mansion rentals Chicago
- Rentals with breakfast Chicago
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