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 house in Little Italy
4.99 out of 5 average rating, 792 reviewsPolk Street Coach House Apartment, Little Italy/Medical Dist
Guest favourite
Guest suite in Chicago
4.97 out of 5 average rating, 239 reviewsStylish Studio in Historic Logan Square
Guest favourite
Flat in Chicago
4.98 out of 5 average rating, 304 reviewsRedesigned Lower Level Studio in Historic Building
Guest favourite
Guest suite in Chicago
4.91 out of 5 average rating, 361 reviewsContemporary, private suite w fireplace
Guest favourite
Flat in Chicago
4.83 out of 5 average rating, 570 reviewsGreat Location! Gold Coast! 07
Guest favourite
Guest suite in North Center
4.96 out of 5 average rating, 107 reviewsModern Garden Apartment in Lincoln Square
Guest favourite
Guest suite in Logan Square
4.97 out of 5 average rating, 230 reviewsPrivate Suite w/ offstreet pkg, at Logan Sq Blu Ln
Guest favourite
Home in Chicago
4.98 out of 5 average rating, 208 reviewsWrigleyville Southport Studio
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
- Rentals with lake access Chicago
- Rentals with an accessible-height bed Chicago
- Rentals with an EV charger Chicago
- Rentals with a balcony Chicago
- Rentals with a washing machine and dryer Chicago
- Rentals with a fireplace Chicago
- Family-friendly rentals Chicago
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- Rentals with a firepit Chicago
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- Flat rentals Chicago
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