Holiday rentals 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
Get the amount of space that is right for you
Popular amenities for Chicago Loop holiday rentals
Other great holiday rentals in Chicago Loop
Guest favourite
Rental unit in Wicker Park
4.95 out of 5 average rating, 268 reviewsHeart of Bucktown
Guest favourite
Loft in Wicker Park
4.94 out of 5 average rating, 104 reviewsCool! 2nd Story Loft. BEST Location! Super CLEAN!
Superhost
Rental unit in Chicago
4.84 out of 5 average rating, 185 reviewsLa Cottage
Superhost
Townhouse in West Town
4.85 out of 5 average rating, 153 reviews⭐️Cozy Garden Unit by Downtown & Blue Line Stop⭐️
Superhost
Rental unit in East Rogers Park
4.89 out of 5 average rating, 112 reviewsLAKESIDE PIED `A TERRE STEPS TO BEACH
Guest favourite
Apartment in Lake View
4.98 out of 5 average rating, 40 reviewsChic & Comfy • Close to Wrigley
Guest favourite
Guest suite in West Loop
4.91 out of 5 average rating, 92 reviewsCozy one-bedroom suite in the heart of West Loop
Guest favourite
Rental unit in Lincoln Park
4.97 out of 5 average rating, 59 reviewsRecently renovated 1 bedroom in the best location!
Quick stats about holiday rentals in Chicago Loop
Total rentals
960 properties
Total number of reviews
31K reviews
Family-friendly rentals
270 properties are a good fit for families
Pet-friendly rentals
520 properties allow pets
Rentals with a pool
470 properties have a pool
Rentals with dedicated workspaces
620 properties have a dedicated workspace
Destinations to explore
- Rentals with an EV charger Chicago Loop
- Fitness-friendly rentals Chicago Loop
- Rentals with a sauna Chicago Loop
- Boutique hotel rentals Chicago Loop
- Monthly Rentals Chicago Loop
- Loft rentals Chicago Loop
- Hotel rentals Chicago Loop
- Family-friendly rentals Chicago Loop
- Rentals with a washing machine and dryer Chicago Loop
- Rentals with a firepit Chicago Loop
- Rentals with pools Chicago Loop
- Rentals with lake access Chicago Loop
- Rentals with breakfast Chicago Loop
- Pet-friendly rentals Chicago Loop
- Rentals with a patio Chicago Loop
- Rentals with outdoor seating Chicago Loop
- Rentals with a fireplace Chicago Loop
- Family-friendly rentals Chicago Loop
- Rentals with beach access Chicago Loop
- Apartment rentals Chicago Loop
- Rentals with a hot tub Chicago Loop
- Flat rentals Chicago Loop
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