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
Home in West Town
4.95 out of 5 average rating, 178 reviewsParadise on the Park
Guest suite in Lincoln Square
4.92 out of 5 average rating, 405 reviewsPrivate Lincoln Square Garden Apt
Apartment in West Town
4.96 out of 5 average rating, 266 reviewsTurquoise Wonder - Clean, Cozy & Stylish Apt
Guest suite in Lincoln Square
4.94 out of 5 average rating, 182 reviewsLincoln Square In-laws Suite: Private Entrance
Apartment in Near North Side
4.82 out of 5 average rating, 490 reviewsGreat Location Studio II
Guest suite in East Pilsen
4.92 out of 5 average rating, 117 reviewsEntirely Private Suite - Urban Oasis - Pilsen/UIC
Townhouse in Near West Side
4.86 out of 5 average rating, 283 reviewsCITY CONDO with GARAGE 7 min Walk to Train
Apartment in Gold Coast
4.88 out of 5 average rating, 145 reviewsCharming Gold Coast One-Bedroom Near Downtown!
Other great vacation rentals in Chicago Loop
Condo in Uptown
4.92 out of 5 average rating, 116 reviewsStunning, Spacious, & Sun-Soaked 1br Uptown Condo
Apartment in West Town
4.92 out of 5 average rating, 334 reviewsBright, Modern Apartment in a Vintage Greystone
Loft in Brighton Park
4.9 out of 5 average rating, 224 reviewsEntire place with free parking.
Apartment in Avondale
4.97 out of 5 average rating, 124 reviewsDesigner Avondale Attic
Apartment in Wicker Park
4.97 out of 5 average rating, 239 reviewsStylish First Flr. Studio. Best Location Division+Hermitage.
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
Guest suite in North Center
4.96 out of 5 average rating, 107 reviewsModern Garden Apartment 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 outdoor seating Chicago Loop
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- Rentals with beach access Chicago Loop
- Family-friendly rentals Chicago Loop
- Rentals with a washer and dryer Chicago Loop
- Boutique hotel rentals Chicago Loop
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- Kid-friendly rentals Chicago Loop
- Fitness-friendly rentals Chicago Loop
- Condo rentals Chicago Loop
- Rentals with pools Chicago Loop
- Pet-friendly rentals Chicago Loop
- Rentals with a fireplace Chicago Loop
- Monthly Rentals Chicago Loop
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- Rentals with lake access Chicago Loop
- Rentals with an EV charger Chicago Loop
- Hotel rentals Chicago Loop
- Rentals with breakfast Chicago Loop
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