Holiday rentals 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
Guest suite in Logan Square
4.97 out of 5 average rating, 226 reviewsPrivate Suite w/ offstreet pkg, at Logan Sq Blu Ln
10–17 Sep
Flat in Chicago
4.96 out of 5 average rating, 263 reviewsTurquoise Wonder - Clean, Cozy & Stylish Apt
3–10 Jan
Home in Berwyn
4.91 out of 5 average rating, 242 reviewsPrivate apartment with retro vibe
8–15 Sep
Home in Chicago
4.89 out of 5 average rating, 333 reviewsPrivate 3rd Floor Apartment
11–18 Feb
Flat in Lincoln Park
4.86 out of 5 average rating, 77 reviewsCozy Lincoln Park Studio - Steps to Zoo!
30 Jan – 6 Feb
Flat in Chicago
4.92 out of 5 average rating, 492 reviews2BR Bursting w/ Character in Hip Logan Square!
27 Mar – 3 Apr
Guest suite in Chicago
4.96 out of 5 average rating, 322 reviewsGorgeous, cozy 1-bedroom Suite in Andersonville
13–20 Apr
Guest house in Little Italy
4.99 out of 5 average rating, 786 reviewsPolk Street Coach House Apartment, Little Italy/Medical Dist
16–23 Nov
Quick stats about holiday 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 Holiday rentals
- Milwaukee Holiday rentals
- Lake Geneva Holiday rentals
- Lake Michigan Beach Holiday rentals
- Saugatuck Holiday rentals
- Evanston Holiday rentals
- Holland Holiday rentals
- South Haven Holiday rentals
- Naperville Holiday rentals
- South Side Holiday rentals
- South Bend Holiday rentals
- New Buffalo Holiday rentals
- Rentals with breakfast Chicago
- Rentals with a firepit Chicago
- Lakehouse rentals Chicago
- Rentals with lake access Chicago
- Rentals with an EV charger Chicago
- Family-friendly rentals Chicago
- Rentals with a sauna Chicago
- Rentals with a washing machine and dryer Chicago
- Apartment rentals Chicago
- Rentals with a hot tub Chicago
- Fitness-friendly rentals Chicago
- Rentals with a fireplace Chicago
- Rentals with a cinema Chicago
- Rentals with outdoor seating Chicago
- Rentals with a patio Chicago
- Loft rentals Chicago
- Townhouse rentals Chicago
- House rentals Chicago
- Rentals with pools Chicago
- Rentals with beach access Chicago
- Boutique hotel rentals Chicago
- Bed and breakfasts Chicago
- Beachfront rentals Chicago
- Flat rentals Chicago
- Waterfront rentals Chicago
- Smoking-friendly rentals Chicago
- Guest house rentals Chicago
- Private suite rentals Chicago
- Rentals with an accessible-height bed Chicago
- Family-friendly rentals Chicago
- Hotel rentals Chicago
- Pet-friendly rentals Chicago
- Rentals with a balcony Chicago
- Mansion rentals Chicago
- Monthly 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