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
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
Guest suite in Lincoln Square
4.95 out of 5 average rating, 243 reviewsGreat location, private entry and patio!
Guest favourite
Home in West Town
4.95 out of 5 average rating, 176 reviewsParadise on the Park
Guest favourite
Apartment in Gold Coast
4.89 out of 5 average rating, 141 reviewsCharming Gold Coast One-Bedroom Near Downtown!
Guest favourite
Apartment in Pilsen Historic District
4.89 out of 5 average rating, 247 reviewsModern
Guest favourite
Condo in Lincoln Park
4.96 out of 5 average rating, 446 reviewsUnique Lincoln Park Duplex Apt
Guest favourite
Apartment in Humboldt Park
4.98 out of 5 average rating, 110 reviewsHumboldt Park Loft
Superhost
Apartment in Chicago
4.84 out of 5 average rating, 177 reviewsThe Cottage
Guest favourite
Guest suite in Lincoln Square
4.94 out of 5 average rating, 180 reviewsLincoln Square In-laws Suite: Private Entrance
Quick stats about holiday 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 beach access Chicago Loop
- Family-friendly rentals Chicago Loop
- Rentals with a washing machine and dryer Chicago Loop
- Fitness-friendly rentals Chicago Loop
- Rentals with an EV charger Chicago Loop
- Loft rentals Chicago Loop
- Rentals with outdoor seating Chicago Loop
- Monthly Rentals Chicago Loop
- Kid-friendly rentals Chicago Loop
- Rentals with a sauna Chicago Loop
- Rentals with a patio Chicago Loop
- Rentals with breakfast Chicago Loop
- Boutique hotel rentals Chicago Loop
- Rentals with a hot tub Chicago Loop
- Hotel rentals Chicago Loop
- Pet-friendly rentals Chicago Loop
- Rentals with lake access Chicago Loop
- Rentals with pools Chicago Loop
- Condo rentals Chicago Loop
- Rentals with a fireplace Chicago Loop
- Apartment rentals Chicago Loop
- Rentals with a fire pit Chicago Loop
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