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
Guest suite in Chicago
4.97 out of 5 average rating, 226 reviewsPrivate Suite w/ offstreet pkg, at Logan Sq Blu Ln
Guest favourite
Home in Berwyn
4.91 out of 5 average rating, 243 reviewsPrivate apartment with retro vibe
Guest favourite
Flat in Cicero
4.98 out of 5 average rating, 204 reviewsCOZY 2Bdr Apt near MDW, Dwtn, United Ctr, Sox, Hwy
Guest favourite
Flat in Chicago
4.96 out of 5 average rating, 267 reviewsCozy loft in Chicago's Uptown
Guest favourite
Flat in Chicago
4.95 out of 5 average rating, 241 reviewsRoscoe Village One Bed Lux Apartment Near Wrigley
Guest favourite
Guest house in Chicago
4.91 out of 5 average rating, 342 reviewsPrivate, Charming, Coach House Loft in Andersonville
Guest favourite
Cabin in Griffith
4.91 out of 5 average rating, 158 reviewsBeautiful Rustic Cabin for Two!
Guest favourite
Home in Chicago
4.95 out of 5 average rating, 123 reviewsCozy & Modern Chic Full House in Trendy Bridgeport
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
- Private suite rentals Chicago
- Rentals with an accessible-height bed Chicago
- Rentals with an EV charger Chicago
- Lakehouse rentals Chicago
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- Monthly Rentals Chicago
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- Bed and breakfasts Chicago
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