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, 106 reviewsLAKESIDE PIED `A TERRE STEPS TO BEACH
Guest favourite
Apartment in West Town
4.96 out of 5 average rating, 265 reviewsTurquoise Wonder - Clean, Cozy & Stylish Apt
Guest favourite
Apartment in Humboldt Park
4.98 out of 5 average rating, 109 reviewsHumboldt Park Loft
Guest favourite
Guest suite in Lincoln Square
4.95 out of 5 average rating, 243 reviewsGreat location, private entry and patio!
Guest favourite
Home in Pilsen Historic District
4.95 out of 5 average rating, 322 reviewsGet Cozy at a Powder-Blue Residence in the Heart of Pilsen
Guest favourite
Loft in Lake View
4.96 out of 5 average rating, 422 reviewsLakeview Loft-Vintage Chicago, Modern Amenities
Guest favourite
Apartment in Lincoln Park
4.99 out of 5 average rating, 197 reviewsExplore Lincoln Park from a Polished Apartment
Guest favourite
Apartment in West Town
4.92 out of 5 average rating, 329 reviewsBright, Modern Apartment in a Vintage Greystone
Destinations to explore
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- Rentals with a sauna Downtown Chicago
- Rentals with a hot tub Downtown Chicago
- Beachfront rentals Downtown Chicago
- Rentals with a washing machine and dryer Downtown Chicago
- Rentals with a patio Downtown Chicago
- Apartment rentals Downtown Chicago
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- Condo rentals Downtown Chicago
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- Rentals with an EV charger Downtown Chicago
- Kid-friendly rentals Downtown Chicago
- Rentals with breakfast Downtown Chicago
- Rentals with pools Downtown Chicago
- Rentals with beach access Downtown Chicago
- Rentals with outdoor seating Downtown Chicago
- Rentals with lake access Downtown Chicago
- Rentals with a home theatre Downtown Chicago
- Pet-friendly rentals Downtown Chicago
- Rentals with a fireplace Downtown Chicago
- Rentals with a fire pit Downtown Chicago
- Waterfront rentals Downtown Chicago
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- Monthly Rentals Downtown Chicago
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- Hotel rentals Downtown Chicago
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