Holiday rentals 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
Flat in Chicago
4.96 out of 5 average rating, 236 reviewsRoscoe Village One Bed Lux Apartment Near Wrigley
17–24 Nov
€ 134 per night
Guest favourite
Guest house in Chicago
4.99 out of 5 average rating, 782 reviewsPolk Street Coach House Apartment, Little Italy/Medical Dist
25 Oct – 1 Nov
€ 173 per night
Guest favourite
Guest suite in Chicago
4.91 out of 5 average rating, 357 reviewsContemporary, private suite w fireplace
5–12 Jan
€ 97 per night
Guest favourite
Guest house in Chicago
4.95 out of 5 average rating, 366 reviewsCozy Coach House
19–26 Aug
€ 137 per night
Guest favourite
Flat in Oak Park
4.85 out of 5 average rating, 527 reviewsLong stays welcome@warm&cute vintage 2BR
24 Sep – 1 Oct
€ 121 per night
Guest favourite
Guest house in Chicago
4.91 out of 5 average rating, 340 reviewsPrivate, Charming, Coach House Loft in Andersonville
3–10 Oct
€ 191 per night
Guest favourite
Flat in Chicago
4.95 out of 5 average rating, 22 reviewsLincoln Square Oasis - Bright, clean studio
17–24 Jan
€ 113 per night
Guest favourite
Home in Berwyn
5.0 out of 5 average rating, 73 reviewsRetro Modern Bungalow | free parking | pets ok
1–8 Dec
€ 148 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 an EV charger Chicago
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