Holiday houses 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
Condo in Chicago
4.97 out of 5 average rating, 332 reviewsLincoln Square Gem!
Guest favourite
Apartment in Chicago
4.97 out of 5 average rating, 120 reviewsDesigner Avondale Attic
Guest favourite
Guest suite in Chicago
4.97 out of 5 average rating, 226 reviewsPrivate Suite w/ offstreet pkg, at Logan Sq Blu Ln
Guest favourite
Apartment in Humboldt Park
4.98 out of 5 average rating, 109 reviewsHumboldt Park Loft
Guest favourite
Apartment in Gold Coast
4.89 out of 5 average rating, 140 reviewsCharming Gold Coast One-Bedroom Near Downtown!
Guest favourite
Guesthouse in Edgewater
4.95 out of 5 average rating, 368 reviewsCozy Coach House
Guest favourite
Apartment in Cicero
4.98 out of 5 average rating, 204 reviewsCOZY 2Bdr Apt near MDW, Dwtn, United Ctr, Sox, Hwy
Guest favourite
Guest suite in Chicago
4.98 out of 5 average rating, 112 reviewsGorgeous Studio 15 Minutes From Ohare!
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
- Kid-friendly rentals Chicago
- Private suite rentals Chicago
- Rentals with an accessible height bed Chicago
- Rentals with an EV charger Chicago
- Lakehouse rentals Chicago
- Fitness-friendly rentals Chicago
- Rentals with lake access Chicago
- Rentals with a home theatre Chicago
- Rentals with outdoor seating Chicago
- Loft rentals Chicago
- Smoking-friendly rentals Chicago
- Rentals with a patio Chicago
- Rentals with a sauna Chicago
- Rentals with a fireplace Chicago
- Townhouse rentals Chicago
- Rentals with breakfast Chicago
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- Hotel rentals Chicago
- Pet-friendly rentals Chicago
- Rentals with a washing machine and dryer Chicago
- Monthly Rentals Chicago
- Mansion rentals Chicago
- Guesthouse rentals Chicago
- Beachfront rentals Chicago
- Family-friendly rentals Chicago
- Rentals with a balcony Chicago
- Rentals with pools Chicago
- Bed and breakfasts Chicago
- Apartment rentals Chicago
- Boutique hotel rentals Chicago
- Condo rentals Chicago
- Rentals with a hot tub Chicago
- House rentals Chicago
- Waterfront rentals Chicago
- Rentals with beach access Chicago
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