Holiday houses in Chicago
Find and book unique accommodation on Airbnb
Top-rated holiday rentals in Chicago
Guests agree: these stays are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Chicago holiday rentals
Other great holiday rentals in Chicago
Apartment in Cicero
4.98 out of 5 average rating, 201 reviewsCOZY 2Bdr Apt near MDW, Dwtn, United Ctr, Sox, Hwy
21 – 28 Mar
Guest suite in Chicago
4.96 out of 5 average rating, 319 reviewsGorgeous, cozy 1-bedroom Suite in Andersonville
13 – 20 Feb
Loft in Wicker Park
4.78 out of 5 average rating, 482 reviewsWicker Park Loft - Walk To Everything!
4 – 11 Nov
Home in Uptown
4.89 out of 5 average rating, 332 reviewsPrivate 3rd Floor Apartment
9 – 16 Dec
Guest suite in Lake View
4.91 out of 5 average rating, 358 reviewsContemporary, private suite w fireplace
16 – 23 Apr
Guesthouse in Chicago
4.99 out of 5 average rating, 783 reviewsPolk Street Coach House Apartment, Little Italy/Medical Dist
25 Oct – 1 Nov
Apartment in Chicago
4.78 out of 5 average rating, 269 reviewsCozy Garden-Subterranean Apartment
26 Sept – 3 Oct
Apartment in Andersonville
4.98 out of 5 average rating, 249 reviewsAndersonville Cozy 1 bedroom basement suite
23 – 30 Oct
Quick stats about accommodation 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 Holiday rentals
- Milwaukee Holiday rentals
- Lake Geneva Accommodation & holiday rentals
- Lake Michigan Beach Accommodation & holiday rentals
- Saugatuck Accommodation & holiday rentals
- Evanston Accommodation & holiday rentals
- Holland Accommodation & holiday rentals
- South Haven Holiday rentals
- Naperville Accommodation & holiday rentals
- South Side Accommodation & holiday rentals
- South Bend Accommodation & holiday rentals
- New Buffalo Holiday rentals
- Rentals with an EV charger Chicago
- Rentals with breakfast Chicago
- Villa rentals Chicago
- Cottage rentals Chicago
- House rentals Chicago
- Rentals with pools Chicago
- Bed and breakfasts Chicago
- Smoking-friendly rentals Chicago
- Rentals with a patio Chicago
- Rentals with a balcony Chicago
- Boutique hotel rentals Chicago
- Rentals with lake access Chicago
- Rentals with a fireplace Chicago
- Wheelchair accessible rentals Chicago
- Rentals with an accessible height bed Chicago
- Condo rentals Chicago
- Hotel rentals Chicago
- Monthly Rentals Chicago
- Pet-friendly rentals Chicago
- Rentals with a washing machine and dryer Chicago
- Kid-friendly rentals Chicago
- Loft rentals Chicago
- Mansion rentals Chicago
- Family-friendly rentals Chicago
- Beachfront rentals Chicago
- Guesthouse rentals Chicago
- Private suite rentals Chicago
- Rentals with a home theatre Chicago
- Rentals with a hot tub Chicago
- Rentals with a sauna Chicago
- Lakehouse rentals Chicago
- Apartment rentals Chicago
- Rentals with a fire pit Chicago
- Rentals with outdoor seating Chicago
- Rentals with beach access Chicago
- Townhouse rentals Chicago
- Waterfront rentals Chicago
- Fitness-friendly rentals 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