Holiday rentals in Chicago Loop
Find and book unique accommodation on Airbnb
Top-rated holiday rentals in Chicago Loop
Guests agree: these stays are highly rated for location, cleanliness and more.
0 of 0 items showing
1 of 3 pages
1 of 3 pages
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
Flat in Pilsen Historic District
4.89 out of 5 average rating, 249 reviewsModern
Guest favourite
Flat in Chicago
4.96 out of 5 average rating, 102 reviewsCute, Clean, Cozy Apartment in Pilsen
Guest favourite
Flat in Logan Square
4.9 out of 5 average rating, 263 reviewsBright & Lofty Bucktown 1br
Guest favourite
Flat in Avondale
4.97 out of 5 average rating, 121 reviewsDesigner Avondale Attic
Guest favourite
Flat in Near North Side
4.82 out of 5 average rating, 488 reviewsGreat Location Studio II
Guest favourite
Guest suite in Lincoln Square
4.97 out of 5 average rating, 369 reviewsPrivate suite in Lincoln Square
Guest favourite
Guest suite in Lincoln Square
4.92 out of 5 average rating, 405 reviewsPrivate Lincoln Square Garden Apt
Guest favourite
Flat in West Town
4.96 out of 5 average rating, 266 reviewsTurquoise Wonder - Clean, Cozy & Stylish Apt
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
31T reviews
Destinations to explore
- Fitness-friendly rentals Chicago Loop
- Rentals with a sauna Chicago Loop
- Rentals with an EV charger Chicago Loop
- Monthly Rentals Chicago Loop
- Loft rentals Chicago Loop
- Boutique hotel rentals Chicago Loop
- Apartment rentals Chicago Loop
- Rentals with beach access Chicago Loop
- Family-friendly rentals Chicago Loop
- Rentals with a washing machine and dryer Chicago Loop
- Family-friendly rentals Chicago Loop
- Rentals with a patio Chicago Loop
- Rentals with outdoor seating Chicago Loop
- Pet-friendly rentals Chicago Loop
- Rentals with lake access Chicago Loop
- Rentals with pools Chicago Loop
- Rentals with a fireplace Chicago Loop
- Rentals with a firepit Chicago Loop
- Hotel rentals Chicago Loop
- Flat rentals Chicago Loop
- Rentals with a hot tub Chicago Loop
- Rentals with breakfast Chicago Loop
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom