Holiday houses in Chicago Loop
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Top-rated holiday rentals in Chicago Loop
Guests agree: these stays are highly rated for location, cleanliness and more.
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Holiday rentals for every style
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Popular amenities for Chicago Loop holiday rentals
Other great holiday rentals in Chicago Loop
Superhost
Home in West Lawn
4.93 out of 5 average rating, 28 reviewsFamily Friendly Duplex/9 min from MDW/Free Parking
Guest favourite
Home in Elmhurst
4.85 out of 5 average rating, 13 reviewsEnamored in Elmhurst
Guest favourite
Apartment in West Town
4.85 out of 5 average rating, 126 reviewsCondo with private terrace, free WIFI and parking
Superhost
Apartment in Jefferson Park
4.85 out of 5 average rating, 13 reviewsCity Gem: Stylish 3BR for Urban Explorers
Guest favourite
Home in Logan Square
4.85 out of 5 average rating, 85 reviewsCalifornia Cottage/4br prime location Logan Square
Superhost
Condo in East Rogers Park
4.79 out of 5 average rating, 28 reviewsSpacious condo with open floor plan and fireplace
Guest favourite
Home in Riverdale
4.94 out of 5 average rating, 53 reviewsBeautiful , fully renovated
Guest favourite
Apartment in Irving Park
4.95 out of 5 average rating, 55 reviewsPerfect 4 BDR apt, Northside, Free parking, CUBS
Quick stats about holiday rentals in Chicago Loop
Total rentals
1K properties
Total number of reviews
25K reviews
Family-friendly rentals
270 properties are a good fit for families
Pet-friendly rentals
540 properties allow pets
Rentals with a pool
470 properties have a pool
Rentals with dedicated workspaces
650 properties have a dedicated workspace
Destinations to explore
- Rentals with beach access Chicago Loop
- Rentals with a patio Chicago Loop
- Fitness-friendly rentals Chicago Loop
- Rentals with a sauna Chicago Loop
- Kid-friendly rentals Chicago Loop
- Loft rentals Chicago Loop
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- Family-friendly rentals Chicago Loop
- Rentals with a washing machine and dryer Chicago Loop
- Apartment rentals Chicago Loop
- Rentals with outdoor seating Chicago Loop
- Pet-friendly rentals Chicago Loop
- Rentals with a home theatre Chicago Loop
- House rentals Chicago Loop
- Rentals with lake access Chicago Loop
- Rentals with a fire pit Chicago Loop
- Rentals with a fireplace Chicago Loop
- Rentals with pools Chicago Loop
- Condo rentals Chicago Loop
- Rentals with a hot tub Chicago Loop
- Hotel rentals Chicago Loop
- Monthly Rentals Chicago Loop
- Rentals with breakfast Chicago Loop
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