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
Apartment in Near North Side
4.89 out of 5 average rating, 379 reviewsGreat Location Studio in the Gold Coast!!
Apartment in The Loop
4.9 out of 5 average rating, 114 reviewsBright 2BR-2BA steps from The Bean & Michigan Ave
Apartment in Humboldt Park
4.98 out of 5 average rating, 111 reviewsHumboldt Park Loft
Apartment in West Town
4.92 out of 5 average rating, 331 reviewsBright, Modern Apartment in a Vintage Greystone
Apartment in West Town
4.97 out of 5 average rating, 458 reviewsFully Furnished Apartment Wicker Park Free Parking
Home in West Town
4.95 out of 5 average rating, 176 reviewsParadise on the Park
Other great vacation rentals in Chicago Loop
Apartment in Chicago
4.98 out of 5 average rating, 137 reviewsModern Apt with style & comfort in Pilsen Chicago
Apartment in Chicago
4.84 out of 5 average rating, 177 reviewsThe Cottage
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!
Apartment in Near South Side
4.83 out of 5 average rating, 23 reviewsCozy Condo near Downtown Chicago
Apartment in Portage Park
4.97 out of 5 average rating, 61 reviewsComfy & Private Chicago Studio
Condo in Lake View
4.96 out of 5 average rating, 28 reviewsChic & Comfy • Close to Wrigley
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
- Boutique hotel rentals Chicago Loop
- Rentals with a sauna Chicago Loop
- Monthly Rentals Chicago Loop
- Kid-friendly rentals Chicago Loop
- Rentals with an EV charger Chicago Loop
- Loft rentals Chicago Loop
- Rentals with a patio Chicago Loop
- Fitness-friendly rentals Chicago Loop
- Rentals with a hot tub Chicago Loop
- Rentals with lake access Chicago Loop
- Rentals with a fireplace Chicago Loop
- Pet-friendly rentals Chicago Loop
- Rentals with outdoor seating Chicago Loop
- Rentals with breakfast Chicago Loop
- Hotel rentals Chicago Loop
- Condo rentals Chicago Loop
- Apartment rentals Chicago Loop
- Rentals with a fire pit Chicago Loop
- Rentals with pools Chicago Loop
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