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
4.98 out of 5 average rating, 110 reviewsHumboldt Park Loft
Guest favourite
Guest suite in Chicago
4.92 out of 5 average rating, 405 reviewsPrivate Lincoln Square Garden Apt
Guest favourite
Guest house in Little Italy
4.99 out of 5 average rating, 791 reviewsPolk Street Coach House Apartment, Little Italy/Medical Dist
Guest favourite
Flat in West Loop
4.87 out of 5 average rating, 220 reviewsGarden Apartment in the Historic Heart of the City
Superhost
Flat in Chicago
4.84 out of 5 average rating, 176 reviewsLa Cottage
Guest favourite
Townhouse in Hoffman Estates
4.91 out of 5 average rating, 296 reviewsa SIMPLE place
Guest favourite
Flat in Near North Side
4.89 out of 5 average rating, 378 reviewsGreat Location Studio in the Gold Coast!!
Guest favourite
Guest suite in Chicago
4.96 out of 5 average rating, 324 reviewsGorgeous, cozy 1-bedroom Suite in Andersonville
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
- Smoking-friendly rentals Chicago
- Private suite rentals Chicago
- Rentals with an accessible-height toilet Chicago
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- Rentals with a sauna Chicago
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- Flat rentals Chicago
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- Monthly Rentals Chicago
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