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
Guest suite in Lincoln Square
4.94 out of 5 average rating, 180 reviewsLincoln Square In-laws Suite: Private Entrance
Apartment in Pilsen Historic District
4.89 out of 5 average rating, 249 reviewsModern
Home in West Town
4.95 out of 5 average rating, 178 reviewsParadise on the Park
Apartment in Chicago
4.96 out of 5 average rating, 102 reviewsCute, Clean, Cozy Apartment in Pilsen
Loft in Pilsen Historic District
4.91 out of 5 average rating, 316 reviewsPilsen Modernist, Creative, Lightfilled Loft
Apartment in West Town
4.96 out of 5 average rating, 266 reviewsTurquoise Wonder - Clean, Cozy & Stylish Apt
Apartment in West Town
4.92 out of 5 average rating, 310 reviewsSpacious & private! Free parking! Great location!
Apartment in West Town
4.92 out of 5 average rating, 332 reviewsBright, Modern Apartment in a Vintage Greystone
Other great vacation rentals in Chicago Loop
Apartment in Logan Square
4.96 out of 5 average rating, 382 reviewsKing Bed, Huge Spa Shower, Dining Destination
Apartment in Wrigleyville
4.93 out of 5 average rating, 191 reviewsTaj Ma-small at Wrigley
Apartment in Lincoln Park
4.87 out of 5 average rating, 276 reviewsHistoric Old Town Flat - Minutes from Downtown!
Apartment in West Town
4.98 out of 5 average rating, 227 reviewsUkrainian Village Garden Retreat
Apartment in Lincoln Park
4.99 out of 5 average rating, 198 reviewsExplore Lincoln Park from a Polished Apartment
Apartment in Roscoe Village
4.96 out of 5 average rating, 246 reviewsRoscoe Village One Bed Lux Apartment Near Wrigley
Guest suite in West Loop
4.92 out of 5 average rating, 85 reviewsCozy one-bedroom suite in the heart of West Loop
Apartment in Chicago
4.97 out of 5 average rating, 67 reviewsLocation! Location! Location!
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 lake access Chicago Loop
- Rentals with breakfast Chicago Loop
- Loft rentals Chicago Loop
- Fitness-friendly rentals Chicago Loop
- Rentals with an EV charger Chicago Loop
- Monthly Rentals Chicago Loop
- Rentals with a hot tub Chicago Loop
- Rentals with a fire pit Chicago Loop
- Apartment rentals Chicago Loop
- Pet-friendly rentals Chicago Loop
- Boutique hotel rentals Chicago Loop
- Rentals with a fireplace Chicago Loop
- Rentals with outdoor seating Chicago Loop
- Hotel rentals Chicago Loop
- Family-friendly rentals Chicago Loop
- Rentals with a washer and dryer Chicago Loop
- Rentals with a patio Chicago Loop
- Rentals with a sauna Chicago Loop
- Rentals with beach access Chicago Loop
- Condo rentals Chicago Loop
- Rentals with pools Chicago Loop
- Kid-friendly rentals Chicago Loop
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