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
Get the amount of space that is right for you
Popular amenities for Downtown Chicago holiday rentals
Other great holiday rentals in Downtown Chicago
Guest favourite
Guest suite in Lake View
4.91 out of 5 average rating, 361 reviewsContemporary, private suite w fireplace
Superhost
Apartment in East Rogers Park
4.89 out of 5 average rating, 107 reviewsLAKESIDE PIED `A TERRE STEPS TO BEACH
Guest favourite
Guest suite in Lincoln Square
4.97 out of 5 average rating, 367 reviewsPrivate suite in Lincoln Square
Guest favourite
Apartment in Humboldt Park
4.98 out of 5 average rating, 110 reviewsHumboldt Park Loft
Guest favourite
Apartment in West Town
4.98 out of 5 average rating, 225 reviewsUkrainian Village Garden Retreat
Guest favourite
Apartment in Lincoln Park
4.99 out of 5 average rating, 197 reviewsExplore Lincoln Park from a Polished Apartment
Guest favourite
Home in West Town
4.95 out of 5 average rating, 173 reviewsParadise on the Park
Guest favourite
Loft in Lake View
4.96 out of 5 average rating, 422 reviewsLakeview Loft-Vintage Chicago, Modern Amenities
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- Rentals with a patio Downtown Chicago
- Rentals with an EV charger Downtown Chicago
- Family-friendly rentals Downtown Chicago
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- Rentals with pools Downtown Chicago
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