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
Flat in Little Italy
4.98 out of 5 average rating, 199 reviewsSpacious 2BR on Quiet St - Free Park/Late Checkout
9–16 Jan
€ 216 per night
Superhost
Flat in Chicago
4.84 out of 5 average rating, 176 reviewsLa Cottage
25 Oct – 1 Nov
€ 94 per night
Guest favourite
Loft in Lake View
4.96 out of 5 average rating, 422 reviewsLakeview Loft-Vintage Chicago, Modern Amenities
15–22 Jan
€ 182 per night
Guest favourite
Guest suite in Lincoln Square
5.0 out of 5 average rating, 297 reviewsPrivate Lincoln Square one bed+bath studio apt.
18–25 Sep
€ 173 per night
Guest favourite
Guest suite in Lincoln Square
4.9 out of 5 average rating, 421 reviewsCozy, Quiet, Garden Getaway!
21–28 Dec
€ 134 per night
Superhost
Flat in Near South Side
4.81 out of 5 average rating, 26 reviewsMcCormick Place 420 friendly 2brs/parking/sleeps 6
30 Jan – 6 Feb
€ 130 per night
Guest favourite
Flat in Portage Park
4.96 out of 5 average rating, 54 reviewsComfy & Private Chicago Studio
6–13 Feb
€ 110 per night
Guest favourite
Flat in Chicago
4.97 out of 5 average rating, 33 reviewsSerene Escape with King Sleep Number Bed, No Fees!
23–30 Nov
€ 121 per night
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- Beachfront rentals Downtown Chicago
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- Rentals with an EV charger Downtown Chicago
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