Holiday houses 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
Apartment in East Rogers Park
4.89 out of 5 average rating, 108 reviewsLAKESIDE PIED `A TERRE STEPS TO BEACH
Superhost
Apartment in Pilsen Historic District
4.87 out of 5 average rating, 207 reviewsSpectacular Pilsen Studio for 2!
Guest favourite
Guest suite in Lincoln Square
4.92 out of 5 average rating, 405 reviewsPrivate Lincoln Square Garden Apt
Guest favourite
Condo in Lincoln Park
4.96 out of 5 average rating, 447 reviewsUnique Lincoln Park Duplex Apt
Superhost
Apartment in Chicago
4.84 out of 5 average rating, 177 reviewsThe Cottage
Guest favourite
Home in West Town
4.95 out of 5 average rating, 176 reviewsParadise on the Park
Superhost
Apartment in Near South Side
4.8 out of 5 average rating, 70 reviewsMcCormick Place Studio/parking/sleeps up to 4
Guest favourite
Condo in Lake View
4.96 out of 5 average rating, 28 reviewsChic & Comfy • Close to Wrigley
Destinations to explore
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- Rentals with a fireplace Downtown Chicago
- Rentals with a washing machine and dryer Downtown Chicago
- Beachfront rentals Downtown Chicago
- Rentals with a home theatre Downtown Chicago
- Rentals with a fire pit Downtown Chicago
- Loft rentals Downtown Chicago
- Pet-friendly rentals Downtown Chicago
- Condo rentals Downtown Chicago
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- Rentals with breakfast Downtown Chicago
- Waterfront rentals Downtown Chicago
- Rentals with a hot tub Downtown Chicago
- Rentals with a patio Downtown Chicago
- Rentals with pools Downtown Chicago
- Hotel rentals Downtown Chicago
- Rentals with beach access Downtown Chicago
- Rentals with lake access Downtown Chicago
- Monthly Rentals Downtown Chicago
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- Rentals with an EV charger Downtown Chicago
- Apartment rentals Downtown Chicago
- Rentals with a sauna Downtown Chicago
- Townhouse rentals Downtown Chicago
- Kid-friendly rentals Downtown Chicago
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