Vacation rentals in Chicago
Find and book unique accommodations on Airbnb
Top-rated vacation rentals in Chicago
Guests agree: these stays 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 vacation rentals
Other great vacation rentals in Chicago
Apartment in Roscoe Village
4.96 out of 5 average rating, 237 reviewsRoscoe Village One Bed Lux Apartment Near Wrigley
Nov. 3 – 10
Loft in Forest Park
4.96 out of 5 average rating, 462 reviewsWalk to Oak Park from a Bright Madison Street Loft
Dec. 9 – 16
Guest suite in Chicago
4.91 out of 5 average rating, 358 reviewsContemporary, private suite w fireplace
Apr. 19 – 26
Home in Chicago
4.89 out of 5 average rating, 332 reviewsPrivate 3rd Floor Apartment
Nov. 29 – Dec. 6
Guesthouse in Little Italy
4.99 out of 5 average rating, 783 reviewsPolk Street Coach House Apartment, Little Italy/Medical Dist
Oct. 25 – Nov. 1
Home in Berwyn
4.92 out of 5 average rating, 237 reviewsPrivate apartment with retro vibe
Sep. 20 – 27
Apartment in Chicago
4.98 out of 5 average rating, 248 reviewsAndersonville Cozy 1 bedroom basement suite
Sep. 10 – 17
Apartment in Chicago
4.96 out of 5 average rating, 321 reviewsBright family-friendly Lincoln Square 2-bed 1-bath
Sep. 28 – Oct. 5
Quick stats about vacation rentals in Chicago
Total rentals
10K properties
Rentals with dedicated workspaces
6.6K properties have a dedicated workspace
Rentals with a pool
1.1K properties have a pool
Pet-friendly rentals
3.3K properties allow pets
Family-friendly rentals
4.8K properties are a good fit for families
Total number of reviews
466K reviews
Destinations to explore
- Downtown Chicago Vacation rentals
- Milwaukee Vacation rentals
- Lake Geneva Vacation rentals
- Lake Michigan Beach Vacation rentals
- Saugatuck Vacation rentals
- Evanston Vacation rentals
- Holland Vacation rentals
- South Haven Vacation rentals
- Naperville Vacation rentals
- South Side Vacation rentals
- South Bend Vacation rentals
- New Buffalo Vacation rentals
- Mansion rentals Chicago
- Hotel rentals Chicago
- Rentals with pools Chicago
- Waterfront rentals Chicago
- Rentals with a sauna Chicago
- Apartment rentals Chicago
- Fitness-friendly rentals Chicago
- Villa rentals Chicago
- Rentals with a washer and dryer Chicago
- Boutique hotel rentals Chicago
- Kid-friendly rentals Chicago
- Loft rentals Chicago
- Lake house rentals Chicago
- Guesthouse rentals Chicago
- Private suite rentals Chicago
- Rentals with a home theater Chicago
- Rentals with a fireplace Chicago
- Cottage rentals Chicago
- Rentals with a patio Chicago
- Monthly Rentals Chicago
- Wheelchair accessible rentals Chicago
- Townhouse rentals Chicago
- Family-friendly rentals Chicago
- Rentals with breakfast Chicago
- Rentals with a balcony Chicago
- Rentals with lake access Chicago
- Rentals with beach access Chicago
- Condo rentals Chicago
- Smoking-friendly rentals Chicago
- House rentals Chicago
- Bed and breakfasts Chicago
- Beachfront rentals Chicago
- Pet-friendly rentals Chicago
- Rentals with a firepit Chicago
- Rentals with outdoor seating Chicago
- Rentals with a hot tub Chicago
- Rentals with an EV charger Chicago
- Rentals with an accessible height bed Chicago
- 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