Vacation rentals in Chicago Loop
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Top-rated vacation rentals in Chicago Loop
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 Chicago Loop vacation rentals
Other great vacation rentals in Chicago Loop
Guest favourite
Apartment in Pilsen Historic District
4.89 out of 5 average rating, 249 reviewsModern
Guest favourite
Apartment in The Loop
4.9 out of 5 average rating, 114 reviewsBright 2BR-2BA steps from The Bean & Michigan Ave
Guest favourite
Apartment in Near North Side
4.89 out of 5 average rating, 379 reviewsGreat Location Studio in the Gold Coast!!
Guest favourite
Apartment in West Town
4.97 out of 5 average rating, 458 reviewsFully Furnished Apartment Wicker Park Free Parking
Guest favourite
Apartment in West Town
4.92 out of 5 average rating, 332 reviewsBright, Modern Apartment in a Vintage Greystone
Guest favourite
Apartment in Humboldt Park
4.98 out of 5 average rating, 111 reviewsHumboldt Park Loft
Guest favourite
Home in West Town
4.95 out of 5 average rating, 178 reviewsParadise on the Park
Guest favourite
Guest suite in Lincoln Square
4.97 out of 5 average rating, 369 reviewsPrivate suite in Lincoln Square
Quick stats about vacation rentals in Chicago Loop
Total rentals
890 properties
Rentals with dedicated workspaces
600 properties have a dedicated workspace
Rentals with a pool
480 properties have a pool
Pet-friendly rentals
460 properties allow pets
Family-friendly rentals
270 properties are a good fit for families
Total number of reviews
31K reviews
Destinations to explore
- Rentals with beach access Chicago Loop
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- Pet-friendly rentals Chicago Loop
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