Vacation rentals in Downtown Chicago
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Top-rated vacation rentals in Downtown Chicago
Guests agree: these stays are highly rated for location, cleanliness, and more.
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Vacation rentals for every style
Get the amount of space that is right for you.
Popular amenities for Downtown Chicago vacation rentals
Other great vacation rentals in Downtown Chicago
Guest favourite
Guest suite in Lincoln Square
4.91 out of 5 average rating, 420 reviewsCozy, Quiet, Garden Getaway!
Mar. 23 – 30
$162 CAD per night
Guest favourite
Loft in Lake View
4.96 out of 5 average rating, 418 reviewsLakeview Loft-Vintage Chicago, Modern Amenities
Nov. 11 – 18
$266 CAD per night
Guest favourite
Apartment in Humboldt Park
4.98 out of 5 average rating, 107 reviewsHumboldt Park Loft
Oct. 15 – 22
$224 CAD per night
Guest favourite
Guest suite in Chicago
4.93 out of 5 average rating, 172 reviewsBike the Lakefront from a Sleek Urban Retreat
Feb. 11 – 18
$211 CAD per night
Guest favourite
Apartment in Logan Square
4.9 out of 5 average rating, 257 reviewsBright & Lofty Bucktown 1br
Jan. 8 – 15
$238 CAD per night
Superhost
Apartment in Chicago
4.81 out of 5 average rating, 86 reviewsMcCormick Pl 420 friendly 1br/1ba parking/sleeps 4
Jan. 21 – 28
$149 CAD per night
Superhost
Apartment in Chicago
4.79 out of 5 average rating, 67 reviewsMcCormick Place Studio/parking/sleeps up to 4
Jan. 17 – 24
$149 CAD per night
Guest favourite
Apartment in Portage Park
4.96 out of 5 average rating, 52 reviewsComfy & Private Chicago Studio
Apr. 3 – 10
$160 CAD per night
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- Rentals with pools Downtown Chicago
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- Waterfront rentals Downtown Chicago
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- Loft rentals Downtown Chicago
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- Rentals with an EV charger Downtown Chicago
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- Rentals with a home theater Downtown Chicago
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