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
Home in West Loop
4.88 out of 5 average rating, 372 reviewsPro Cleaned & Isolated West Loop Coach House
Feb. 7 – 14
$252 CAD per night
Guest favourite
Apartment in Wrigleyville
4.93 out of 5 average rating, 187 reviewsTaj Ma-small at Wrigley
Feb. 19 – 26
$225 CAD per night
Guest favourite
Home in Chicago
4.95 out of 5 average rating, 121 reviewsCozy & Modern Chic Full House in Trendy Bridgeport
Apr. 6 – 13
$236 CAD per night
Guest favourite
Home in West Loop
4.97 out of 5 average rating, 318 reviewsCozy garden apartment historic Jackson Bvld.
Mar. 10 – 15
$317 CAD per night
Superhost
Apartment in Chicago
4.78 out of 5 average rating, 87 reviewsMcCormick Place Studio/parking/sleeps up to 4
Jan. 1 – 8
$179 CAD per night
Superhost
Apartment in West Town
5.0 out of 5 average rating, 19 reviewsThe Secret West Loop Oasis/walk to Fulton market
Feb. 18 – 25
$178 CAD per night
Guest favourite
Apartment in Chicago
4.96 out of 5 average rating, 52 reviewsComfy & Private Chicago Studio
Feb. 2 – 9
$160 CAD per night
Guest favourite
Apartment in Chicago
4.89 out of 5 average rating, 57 reviewsMcCormick 2br/2ba Oasis Parking/Patio/Gym/sleeps 6
Feb. 13 – 20
$183 CAD per night
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- Rentals with a sauna Downtown Chicago
- Rentals with a firepit Downtown Chicago
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- Smoking-friendly rentals Downtown Chicago
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- Rentals with a washer and dryer Downtown Chicago
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- Rentals with an EV charger Downtown Chicago
- Rentals with a hot tub Downtown Chicago
- Loft rentals Downtown Chicago
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- Rentals with a home theater Downtown Chicago
- Rentals with a fireplace Downtown Chicago
- House rentals Downtown Chicago
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- Kid-friendly rentals Downtown Chicago
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