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
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 Lincoln Square
4.97 out of 5 average rating, 365 reviewsPrivate suite in Lincoln Square
Guest favourite
Home in Roscoe Village
4.94 out of 5 average rating, 212 reviewsModern Home RoscoeVillage/Wrigley Free St Parking
Guest favourite
Home in Pilsen Historic District
4.95 out of 5 average rating, 321 reviewsGet Cozy at a Powder-Blue Residence in the Heart of Pilsen
Guest favourite
Flat in Humboldt Park
4.98 out of 5 average rating, 109 reviewsHumboldt Park Loft
Guest favourite
Flat in Uptown
4.96 out of 5 average rating, 267 reviewsCozy loft in Chicago's Uptown
Guest favourite
Guest suite in Lake View
4.91 out of 5 average rating, 359 reviewsContemporary, private suite w fireplace
Superhost
Flat in Near South Side
4.79 out of 5 average rating, 67 reviewsMcCormick Place Studio/parking/sleeps up to 4
Superhost
Flat in West Town
5.0 out of 5 average rating, 19 reviewsThe Secret West Loop Oasis/walk to Fulton market
Destinations to explore
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- Rentals with an EV charger Downtown Chicago
- Rentals with beach access Downtown Chicago
- House rentals Downtown Chicago
- Boutique hotel rentals Downtown Chicago
- Rentals with breakfast Downtown Chicago
- Rentals with a firepit Downtown Chicago
- Pet-friendly rentals Downtown Chicago
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- Waterfront rentals Downtown Chicago
- Rentals with a cinema Downtown Chicago
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- Rentals with a patio Downtown Chicago
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- Rentals with pools Downtown Chicago
- Monthly Rentals Downtown Chicago
- Rentals with a fireplace Downtown Chicago
- Rentals with lake access Downtown Chicago
- Flat rentals Downtown Chicago
- Rentals with a washing machine and dryer Downtown Chicago
- Rentals with a sauna Downtown Chicago
- Townhouse rentals Downtown Chicago
- Apartment rentals Downtown Chicago
- Rentals with outdoor seating Downtown Chicago
- Family-friendly rentals Downtown Chicago
- Rentals with a hot tub Downtown Chicago
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