Chicago Loop vacation rentals
Book unique vacation rentals, houses, and more on Airbnb
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
Apartment in Avondale
4.97 out of 5 average rating, 118 reviewsDesigner Avondale Attic
Home in Bridgeport
4.95 out of 5 average rating, 121 reviewsCozy & Modern Chic Full House in Trendy Bridgeport
Apartment in West Town
4.98 out of 5 average rating, 220 reviewsUkrainian Village Garden Retreat
Guest suite in Lincoln Square
4.97 out of 5 average rating, 362 reviewsPrivate suite in Lincoln Square
Apartment in Pilsen Historic District
4.89 out of 5 average rating, 243 reviewsModern
Apartment in Lincoln Square
4.94 out of 5 average rating, 191 reviewsSpacious, light-drenched studio-private entrance!
Apartment in Bridgeport
4.98 out of 5 average rating, 171 reviewsBridgeport Garden Apartment
Townhouse in Near West Side
4.85 out of 5 average rating, 276 reviewsCITY CONDO with GARAGE 7 min Walk to Train
Other great vacation rentals in Chicago Loop
Apartment in Wrigleyville
4.93 out of 5 average rating, 187 reviewsTaj Ma-small at Wrigley
Apartment in Gold Coast
4.89 out of 5 average rating, 140 reviewsCharming Gold Coast One-Bedroom Near Downtown!
Guest suite in East Pilsen
4.92 out of 5 average rating, 115 reviewsEntirely Private Suite - Urban Oasis - Pilsen/UIC
Apartment in Lincoln Park
4.99 out of 5 average rating, 194 reviewsExplore Lincoln Park from a Polished Apartment
Apartment in Uptown
4.96 out of 5 average rating, 266 reviewsCozy loft in Chicago's Uptown
Apartment in Logan Square
4.92 out of 5 average rating, 491 reviews2BR Bursting w/ Character in Hip Logan Square!
Guest suite in West Loop
4.91 out of 5 average rating, 81 reviewsCozy one-bedroom suite in the heart of West Loop
Apartment in Chicago
4.78 out of 5 average rating, 87 reviewsMcCormick Place Studio/parking/sleeps up to 4
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
- Apartment rentals Chicago Loop
- Family-friendly rentals Chicago Loop
- Rentals with an EV charger Chicago Loop
- Rentals with breakfast Chicago Loop
- Rentals with a patio Chicago Loop
- Rentals with beach access Chicago Loop
- Loft rentals Chicago Loop
- Hotel rentals Chicago Loop
- Rentals with a sauna Chicago Loop
- Rentals with pools Chicago Loop
- Pet-friendly rentals Chicago Loop
- Boutique hotel rentals Chicago Loop
- Fitness-friendly rentals Chicago Loop
- Rentals with a fireplace Chicago Loop
- Monthly Rentals Chicago Loop
- Rentals with a fire pit Chicago Loop
- Rentals with outdoor seating Chicago Loop
- Kid-friendly rentals Chicago Loop
- Condo rentals Chicago Loop
- Rentals with a hot tub Chicago Loop
- Rentals with a washer and dryer Chicago Loop
- Rentals with lake access Chicago Loop
- Cabins United States
- Treehouses United States
- Glamping United States
- Tiny Houses United States
- Beach Houses United States
- Campers and RVs United States
- Lakehouses United States
- 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
- Family travel hub Tips and inspiration
- Family budget travel Get there for less
- Vacation ideas for any budget Make it special without making it spendy
- Travel Europe on a budget How to take the kids to Europe for less
- Outdoor adventure Explore nature with the family
- Bucket list national parks Must-see parks for family travel
- Kid-friendly state parks Check out these family-friendly hikes