Chicago Loop vacation rentals
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Top-rated vacation rentals in Chicago Loop
Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.
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
Condo in Lincoln Square
4.97 out of 5 average rating, 338 reviewsLincoln Square Gem!
Apartment in Avondale
4.97 out of 5 average rating, 124 reviewsDesigner Avondale Attic
Apartment in West Town
4.92 out of 5 average rating, 334 reviewsBright, Modern Apartment in a Vintage Greystone
Apartment in West Town
4.96 out of 5 average rating, 266 reviewsTurquoise Wonder - Clean, Cozy & Stylish Apt
Loft in Brighton Park
4.9 out of 5 average rating, 224 reviewsEntire place with free parking.
Apartment in Near North Side
4.89 out of 5 average rating, 380 reviewsGreat Location Studio in the Gold Coast!!
Guest suite in Lincoln Square
4.92 out of 5 average rating, 405 reviewsPrivate Lincoln Square Garden Apt
Apartment in Logan Square
4.96 out of 5 average rating, 383 reviewsKing Bed, Huge Spa Shower, Dining Destination
Other great vacation rentals in Chicago Loop
Guest suite in North Center
4.96 out of 5 average rating, 107 reviewsModern Garden Apartment in Lincoln Square
Guest suite in East Pilsen
4.92 out of 5 average rating, 117 reviewsEntirely Private Suite - Urban Oasis - Pilsen/UIC
Guest suite in Chicago
4.93 out of 5 average rating, 177 reviewsBike the Lakefront from a Sleek Urban Retreat
Apartment in Roscoe Village
4.96 out of 5 average rating, 246 reviewsRoscoe Village One Bed Lux Apartment Near Wrigley
Apartment in East Rogers Park
4.89 out of 5 average rating, 108 reviewsLAKESIDE PIED `A TERRE STEPS TO BEACH
Apartment in Logan Square
4.92 out of 5 average rating, 497 reviews2BR Bursting w/ Character in Hip Logan Square!
Guest suite in Lincoln Square
4.95 out of 5 average rating, 245 reviewsGreat location, private entry and patio!
Guest suite in West Loop
4.92 out of 5 average rating, 86 reviewsCozy one-bedroom suite in the heart of West Loop
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
- Boutique hotel rentals Chicago Loop
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- Loft rentals Chicago Loop
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- Monthly Rentals Chicago Loop
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- Rentals with a washer and dryer Chicago Loop
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- Kid-friendly rentals Chicago Loop
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- Apartment rentals Chicago Loop
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- Hotel rentals Chicago Loop
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- Condo rentals Chicago Loop
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