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
Condo in Lincoln Square
Lincoln Square Gem!
Condo in Little Italy
Private hot tub - King bed suite - Free parking
Guest suite in North Center
Modern Garden Apartment in Lincoln Square
Rental unit in Little Italy
Spacious 2BR on Quiet St - Free Park/Late Checkout
Rental unit in West Town
Bright, Modern Apartment in a Vintage Greystone
Rental unit in West Town
Spacious & private! Free parking! Great location!
Rental unit in Chicago
Cute, Clean, Cozy Apartment in Pilsen
Home in Bridgeport
Cozy & Modern Chic Full House in Trendy Bridgeport
Other great vacation rentals in Chicago Loop
Guest suite in Lincoln Square
Great location, private entry and patio!
Rental unit in Chicago
The Cottage
Guest suite in Chicago
Bike the Lakefront from a Sleek Urban Retreat
Guest suite in Lincoln Square
Private Lincoln Square Garden Apt
Guesthouse in Andersonville
Private, Charming, Coach House Loft in Andersonville
Rental unit in Bridgeport
Bridgeport Garden Apartment
Guest suite in Lake View
1 mile from Wrigley Field
Rental unit in Logan Square
King Bed, Huge Spa Shower, Dining Destination
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
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- Rentals with a washer and dryer Chicago Loop
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- Rentals with a sauna Chicago Loop
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- Rentals with pools Chicago Loop
- Rentals with lake access Chicago Loop
- Rentals with a fire pit Chicago Loop
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- Hotel rentals Chicago Loop
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