Vacation rentals in Chicago Loop
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Top-rated vacation rentals in Chicago Loop
Guests agree: these stays are highly rated for location, cleanliness, and more.
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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 favourite
Rental unit in Chicago
Modern Apt with style & comfort in Pilsen Chicago
Guest favourite
Rental unit in Chicago
Cute, Clean, Cozy Apartment in Pilsen
Guest favourite
Rental unit in Gold Coast
Charming Gold Coast One-Bedroom Near Downtown!
Guest favourite
Rental unit in West Town
Turquoise Wonder - Clean, Cozy & Stylish Apt
Superhost
Rental unit in Near North Side
Great Location Studio III
Guest favourite
Guest suite in Lincoln Square
Great location, private entry and patio!
Guest favourite
Home in West Town
Paradise on the Park
Guest favourite
Guest suite in West Loop
Cozy one-bedroom suite in the heart of West Loop
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 firepit Chicago Loop
- Rentals with a hot tub Chicago Loop
- Hotel rentals Chicago Loop
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