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
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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, 173 reviewsParadise on the Park
Apartment in Pilsen Historic District
4.89 out of 5 average rating, 247 reviewsModern
Condo in Lincoln Park
4.96 out of 5 average rating, 445 reviewsUnique Lincoln Park Duplex Apt
Apartment in Humboldt Park
4.98 out of 5 average rating, 110 reviewsHumboldt Park Loft
Apartment in Chicago
4.96 out of 5 average rating, 101 reviewsCute, Clean, Cozy Apartment in Pilsen
Guest suite in Lincoln Square
4.94 out of 5 average rating, 180 reviewsLincoln Square In-laws Suite: Private Entrance
Guest suite in Lincoln Square
4.97 out of 5 average rating, 367 reviewsPrivate suite in Lincoln Square
Apartment in West Town
4.92 out of 5 average rating, 329 reviewsBright, Modern Apartment in a Vintage Greystone
Other great vacation rentals in Chicago Loop
Loft in Pilsen Historic District
4.91 out of 5 average rating, 313 reviewsPilsen Modernist, Creative, Lightfilled Loft
Guest suite in Lincoln Square
4.95 out of 5 average rating, 243 reviewsGreat location, private entry and patio!
Apartment in Roscoe Village
4.95 out of 5 average rating, 244 reviewsRoscoe Village One Bed Lux Apartment Near Wrigley
Apartment in West Town
4.89 out of 5 average rating, 475 reviewsiKlektik House Chicago / Robin
Guest suite in Lake View
4.91 out of 5 average rating, 361 reviewsContemporary, private suite w fireplace
Guest suite in East Pilsen
4.92 out of 5 average rating, 116 reviewsEntirely Private Suite - Urban Oasis - Pilsen/UIC
Guesthouse in Edgewater
4.95 out of 5 average rating, 369 reviewsCozy Coach House
Guest suite in Bridgeport
4.95 out of 5 average rating, 191 reviewsAttic cozy guests suite near South Loop in Chicago
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
- Family-friendly rentals Chicago Loop
- Rentals with a washer and dryer Chicago Loop
- Fitness-friendly rentals Chicago Loop
- Rentals with an EV charger Chicago Loop
- Loft rentals Chicago Loop
- Rentals with outdoor seating Chicago Loop
- Monthly Rentals Chicago Loop
- Kid-friendly rentals Chicago Loop
- Rentals with a sauna Chicago Loop
- Rentals with a patio Chicago Loop
- Rentals with breakfast Chicago Loop
- Boutique hotel rentals Chicago Loop
- Rentals with a hot tub Chicago Loop
- Hotel rentals Chicago Loop
- Pet-friendly rentals Chicago Loop
- Rentals with lake access Chicago Loop
- Rentals with pools Chicago Loop
- Condo rentals Chicago Loop
- Rentals with a fireplace Chicago Loop
- Apartment rentals Chicago Loop
- Rentals with a fire pit Chicago Loop
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