
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
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Popular amenities for Chicago holiday rentals
Other great holiday rentals in Chicago
Superhost

Home in West Lawn
4.94 out of 5 average rating, 36 reviewsFamily Friendly Duplex/9 min from MDW/Free Parking
Guest favourite

Flat in West Town
4.85 out of 5 average rating, 127 reviewsCondo with private terrace, free WIFI and parking
Top guest favourite

Flat in Albany Park
4.95 out of 5 average rating, 41 reviewsElegant 4Bedroom with Free Parking in Albany Park
Superhost

Flat in Jefferson Park
4.65 out of 5 average rating, 20 reviewsCity Gem: Stylish 3BR for Urban Explorers
Superhost

Apartment in East Rogers Park
4.79 out of 5 average rating, 29 reviewsSpacious condo with open floor plan and fireplace
Top guest favourite

Home in Lombard
5 out of 5 average rating, 22 reviewsSpacious Home in Chicago Suburbs
Guest favourite

Home in Gary
4.96 out of 5 average rating, 72 reviewsPrivate 5 Star 2 bedroom modern city farmhouse
Top guest favourite

Home in Chicago
5 out of 5 average rating, 18 reviewsComfy Home Away From Home
Quick stats about holiday rentals in Chicago
Total rentals
11K properties
Total number of reviews
5.3L reviews
Family-friendly rentals
5.2K properties are a good fit for families
Pet-friendly rentals
3.6K properties allow pets
Rentals with a pool
1.2K properties have a pool
Rentals with dedicated workspaces
7K properties have a dedicated workspace
Destinations to explore
- Downtown Chicago Holiday rentals
- Milwaukee Holiday rentals
- Lake Geneva Holiday rentals
- West Side Holiday rentals
- North Side Holiday rentals
- South Bend Holiday rentals
- Lake Michigan Beach Holiday rentals
- South Side Holiday rentals
- Evanston Holiday rentals
- Holland Holiday rentals
- South Haven Holiday rentals
- Saugatuck Holiday rentals
- Rentals with a sauna Chicago
- Rentals with an accessible-height bed Chicago
- Rentals with a patio Chicago
- Fitness-friendly rentals Chicago
- Rentals with a cinema Chicago
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- Bed and breakfasts Chicago
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- House rentals Chicago
- Loft rentals Chicago
- Mansion rentals Chicago
- Townhouse rentals Chicago
- Rentals with pools Chicago
- Rentals with beach access Chicago
- Apartment rentals Chicago
- Rentals with a hot tub Chicago
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