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.
0 of 0 items showing
1 of 3 pages
1 of 3 pages
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
Guest favourite
Apartment in Chicago
4.96 out of 5 average rating, 266 reviewsCozy loft in Chicago's Uptown
Oct. 20 – 27
$189 CAD per night
Guest favourite
Apartment in Chicago
4.96 out of 5 average rating, 323 reviewsBright family-friendly Lincoln Square 2-bed 1-bath
Dec. 18 – 25
$229 CAD per night
Guest favourite
Apartment in Roscoe Village
4.96 out of 5 average rating, 238 reviewsRoscoe Village One Bed Lux Apartment Near Wrigley
Nov. 19 – 26
$192 CAD per night
Guest favourite
Guesthouse in Chicago
4.95 out of 5 average rating, 367 reviewsCozy Coach House
Aug. 19 – 26
$197 CAD per night
Guest favourite
Guest suite in Logan Square
4.97 out of 5 average rating, 226 reviewsPrivate Suite w/ offstreet pkg, at Logan Sq Blu Ln
Sep. 23 – 30
$208 CAD per night
Guest favourite
Apartment in Logan Square
4.93 out of 5 average rating, 207 reviewsCozy Private Coach House
Jul. 3 – 10
$254 CAD per night
Guest favourite
Home in Chicago
4.89 out of 5 average rating, 332 reviewsPrivate 3rd Floor Apartment
Jan. 16 – 23
$220 CAD per night
Guest favourite
Guesthouse in Andersonville
4.91 out of 5 average rating, 342 reviewsPrivate, Charming, Coach House Loft in Andersonville
Dec. 7 – 14
$274 CAD per night
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
- Rentals with a balcony Chicago
- Rentals with a washer and dryer Chicago
- Monthly Rentals Chicago
- Townhouse rentals Chicago
- Rentals with a fireplace Chicago
- Rentals with a patio Chicago
- Rentals with an accessible height bed Chicago
- Rentals with a sauna Chicago
- Rentals with a hot tub Chicago
- Rentals with breakfast Chicago
- Boutique hotel rentals Chicago
- Rentals with an EV charger Chicago
- Rentals with a firepit Chicago
- Rentals with outdoor seating Chicago
- Beachfront rentals Chicago
- Cottage rentals Chicago
- Pet-friendly rentals Chicago
- Rentals with beach access Chicago
- Fitness-friendly rentals Chicago
- Mansion rentals Chicago
- Guesthouse rentals Chicago
- Private suite rentals Chicago
- House rentals Chicago
- Rentals with pools Chicago
- Smoking-friendly rentals Chicago
- Kid-friendly rentals Chicago
- Loft rentals Chicago
- Family-friendly rentals Chicago
- Apartment rentals Chicago
- Lake house rentals Chicago
- Hotel rentals Chicago
- Rentals with lake access Chicago
- Waterfront rentals Chicago
- Bed and breakfasts Chicago
- Condo rentals Chicago
- Rentals with a home theater 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