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
Home in Chicago
4.89 out of 5 average rating, 332 reviewsPrivate 3rd Floor Apartment
25 Oct – 1 Nov
₹10,456 per night
Guest favourite
Flat in Lincoln Park
4.83 out of 5 average rating, 208 reviewsCozy Lincoln Park Studio - Steps to Zoo!
10–17 Jan
₹9,083 per night
Guest favourite
Flat in Lincoln Square
4.78 out of 5 average rating, 269 reviewsCozy Garden-Subterranean Apartment
24 Sep – 1 Oct
₹8,589 per night
Guest favourite
Guest suite in Chicago
4.91 out of 5 average rating, 358 reviewsContemporary, private suite w fireplace
22–29 Oct
₹6,509 per night
Guest favourite
Flat in Chicago
4.98 out of 5 average rating, 249 reviewsAndersonville Cozy 1 bedroom basement suite
10–17 Jan
₹10,446 per night
Guest favourite
Loft in Forest Park
4.96 out of 5 average rating, 463 reviewsWalk to Oak Park from a Bright Madison Street Loft
9–16 Dec
₹10,658 per night
Guest favourite
Flat in Chicago
4.97 out of 5 average rating, 251 reviewsSpacious 1BR apartment in a central location
23–30 Sep
₹8,332 per night
Guest favourite
Flat in Chicago
4.96 out of 5 average rating, 321 reviewsBright family-friendly Lincoln Square 2-bed 1-bath
6–13 Dec
₹11,065 per night
Quick stats about holiday rentals in Chicago
Total rentals
10T properties
Rentals with dedicated workspaces
6.6T properties have a dedicated workspace
Rentals with a pool
1.1T properties have a pool
Pet-friendly rentals
3.3T properties allow pets
Family-friendly rentals
4.8T properties are a good fit for families
Total number of reviews
4.7L 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
- Bed and breakfasts Chicago
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- Monthly Rentals Chicago
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