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
Rental unit in Chicago
Cute, Clean, Cozy Apartment in Pilsen
Rental unit in Near North Side
Great Location Studio III
Rental unit in Chicago
Modern Apt with style & comfort in Pilsen Chicago
Rental unit in Gold Coast
Charming Gold Coast One-Bedroom Near Downtown!
Rental unit in West Town
Turquoise Wonder - Clean, Cozy & Stylish Apt
Home in West Town
Paradise on the Park
Guest suite in Lincoln Square
Great location, private entry and patio!
Rental unit in West Town
Spacious & private! Free parking! Great location!
Other great vacation rentals in Chicago Loop
Rental unit in Humboldt Park
Humboldt Park Loft
Rental unit in East Rogers Park
LAKESIDE PIED `A TERRE STEPS TO BEACH
Rental unit in Chicago
McCormick Place Studio/parking/sleeps up to 4
Guest suite in West Loop
Cozy one-bedroom suite in the heart of West Loop
Rental unit in Chicago
Location! Location! Location!
Rental unit in Chicago
Cozy Condo near Downtown Chicago
Rental unit in Portage Park
Comfy & Private Chicago Studio
Condo in Lake View
Chic & 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 outdoor seating Chicago Loop
- Kid-friendly rentals Chicago Loop
- Monthly Rentals Chicago Loop
- Boutique hotel rentals Chicago Loop
- Fitness-friendly rentals Chicago Loop
- Loft rentals Chicago Loop
- Family-friendly rentals Chicago Loop
- Rentals with a washer and dryer Chicago Loop
- Rentals with beach access Chicago Loop
- Rentals with a patio Chicago Loop
- Rentals with an EV charger Chicago Loop
- Rentals with breakfast Chicago Loop
- Apartment rentals Chicago Loop
- Pet-friendly rentals Chicago Loop
- Condo rentals Chicago Loop
- Rentals with a sauna Chicago Loop
- Rentals with a fireplace Chicago Loop
- Rentals with pools Chicago Loop
- Rentals with lake access Chicago Loop
- Rentals with a fire pit Chicago Loop
- Rentals with a hot tub Chicago Loop
- Hotel rentals Chicago Loop
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