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 Chicago
4.98 out of 5 average rating, 111 reviewsGorgeous Studio 15 Minutes From Ohare!
13–20 Sep
$121 SGD per night
Guest favourite
Apartment in Lincoln Square
4.98 out of 5 average rating, 329 reviewsLincoln Square Gem!
13–20 Oct
$197 SGD per night
Guest favourite
Guest house in Chicago
4.95 out of 5 average rating, 366 reviewsCozy Coach House
5–12 May
$123 SGD per night
Guest favourite
Townhouse in Chicago
4.85 out of 5 average rating, 275 reviewsCITY CONDO with GARAGE 7 min Walk to Train
3–10 Nov
$127 SGD per night
Guest favourite
Guest suite in Chicago
4.91 out of 5 average rating, 358 reviewsContemporary, private suite w fireplace
16–23 Apr
$106 SGD per night
Guest favourite
Home in West Town
4.95 out of 5 average rating, 171 reviewsParadise on the Park
29 Nov – 6 Dec
$202 SGD per night
Guest favourite
Home in Bridgeport
4.95 out of 5 average rating, 120 reviewsCozy & Modern Chic Full House in Trendy Bridgeport
13–20 Mar
$167 SGD per night
Guest favourite
Guest suite in Lincoln Square
4.97 out of 5 average rating, 361 reviewsPrivate suite in Lincoln Square
30 Sep – 7 Oct
$144 SGD per night
Destinations to explore
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- Apartment rentals Downtown Chicago
- Rentals with a fireplace Downtown Chicago
- Pet-friendly rentals Downtown Chicago
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- Rentals with a sauna Downtown Chicago
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- House rentals Downtown Chicago
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- Hotel rentals Downtown Chicago
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- Waterfront rentals Downtown Chicago
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