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
Apartment in Chicago
4.98 out of 5 average rating, 328 reviewsLincoln Square Gem!
4–11 Oct
€ 180 per night
Guest favourite
Flat in Chicago
4.96 out of 5 average rating, 237 reviewsRoscoe Village One Bed Lux Apartment Near Wrigley
9–16 Dec
€ 133 per night
Guest favourite
Home in Chicago
4.89 out of 5 average rating, 332 reviewsPrivate 3rd Floor Apartment
26 Nov – 3 Dec
€ 153 per night
Guest favourite
Guest suite in Chicago
4.95 out of 5 average rating, 174 reviews1 mile from Wrigley Field
5–12 Sep
€ 185 per night
Guest favourite
Loft in Forest Park
4.96 out of 5 average rating, 462 reviewsWalk to Oak Park from a Bright Madison Street Loft
9–16 Dec
€ 143 per night
Guest favourite
Flat in Chicago
4.78 out of 5 average rating, 269 reviewsCozy Garden-Subterranean Apartment
24 Sep – 1 Oct
€ 123 per night
Guest favourite
Flat in Chicago
4.98 out of 5 average rating, 296 reviewsRedesigned Lower Level Studio in Historic Building
27 Aug – 3 Sep
€ 174 per night
Guest favourite
Flat in Oak Park
4.85 out of 5 average rating, 527 reviewsLong stays welcome@warm&cute vintage 2BR
28 Sep – 5 Oct
€ 121 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
- Family-friendly rentals Chicago
- Rentals with a sauna Chicago
- Family-friendly rentals Chicago
- Loft rentals Chicago
- Pet-friendly rentals Chicago
- Boutique hotel rentals Chicago
- Rentals with lake access Chicago
- House rentals Chicago
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- Wheelchair-accessible rentals Chicago
- Rentals with an EV charger Chicago
- Waterfront rentals Chicago
- Apartment rentals Chicago
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- Rentals with a washing machine and dryer Chicago
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- Monthly Rentals Chicago
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- Villa rentals Chicago
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