
Holiday rentals in Downtown Chicago
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Top-rated holiday rentals in Downtown 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 Downtown Chicago holiday rentals
Other great holiday rentals in Downtown Chicago
Superhost

Home in Chicago
4.94 out of 5 average rating, 36 reviewsFamily Friendly Duplex/9 min from MDW/Free Parking
Superhost

Home in Schaumburg
4.8 out of 5 average rating, 81 reviewsSpacious 5 Bedroom 1 Level Renovated Modern House
Top guest favourite

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

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

Apartment in Chicago
4.79 out of 5 average rating, 29 reviewsSpacious condo with open floor plan and fireplace
Superhost

Home in Cicero
4.79 out of 5 average rating, 173 reviewsSpacious whole apt near shopping and city
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
Destinations to explore
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- Waterfront rentals Downtown Chicago
- Rentals with a washing machine and dryer Downtown Chicago
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- Loft rentals Downtown Chicago
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- Rentals with a fireplace Downtown Chicago
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