Hotel holiday rentals in Chicago
Find and book unique hotels on Airbnb
Top-rated hotels in Chicago
Guests agree: These hotels 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 hotels
Family-Friendly hotels
Aparthotel in Chicago
4.85 out of 5 average rating, 20 reviews2BD/2BA in Charming & Vibrant Andersonville
Boutique hotel in Chicago
4.67 out of 5 average rating, 6 reviews1BD/1BA Steps Away from Local Shops, Entertainment
Hotel room in Uptown
4.98 out of 5 average rating, 44 reviews1BD/1BA Boutique Suite Near Wrigley, Uptown
Boutique hotel in Chicago
4.97 out of 5 average rating, 38 reviews1BD/1BA Suite with Full Kitchen, Balcony w/ Grill
Hotel room in Chicago
4.91 out of 5 average rating, 34 reviews2BD/2BA Near Concert Venues, Wrigley Field
Shared hotel room in Chicago
4.58 out of 5 average rating, 81 reviewsHotel Perks - Private Bedroom | Private Bathroom
Hotel room in Chicago
4.47 out of 5 average rating, 3683 reviewsHotel Perks - Private Bedroom | Private Bathroom
Hotel room in Chicago
4.47 out of 5 average rating, 15 reviewsHotel Perks - Private Bedroom | Private Bathroom
Hotels with a pool
Hotel in Westmont
4.5 out of 5 average rating, 48 reviewsKing Bed with a private tub (breakfast included)
Hotel in Chicago
4.83 out of 5 average rating, 12 reviewsHaven of Serenity! Pets Allowed, Onsite Pool
Hotel in Chicago
5.0 out of 5 average rating, 10 reviewsLight-flooded rooms and city views
Hotel in Chicago
5.0 out of 5 average rating, 5 reviewsComfort and Relaxation! Parking, Near Navy Pier
Hotel in Chicago
4.5 out of 5 average rating, 6 reviewsLarge Unit Close to the Millennium Park! Parking!
Hotel in Schaumburg
3.83 out of 5 average rating, 6 reviews"Radisson Hotel Schaumburg"
Hotel in Gold Coast
120-yr-old landmark with floor-to-ceiling views
Hotel in Chicago
4.71 out of 5 average rating, 7 reviewsRelax and Unwind! Close to Water Tower Chicago!
Quick stats about hotel rentals in Chicago
Total rentals
240 properties
Rentals with a pool
40 properties have a pool
Pet-friendly rentals
80 properties allow pets
Family-friendly rentals
60 properties are a good fit for families
Total number of reviews
3.5K reviews
Nightly prices starting at
$106 AUD before taxes and fees
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
- Schaumburg Accommodation & holiday rentals
- Aparthotel rentals United States
- Boutique hotel rentals United States
- Hotel rentals United States
- Rentals with a home theatre Chicago
- Rentals with outdoor seating Chicago
- Rentals with breakfast Chicago
- Rentals with a fire pit Chicago
- Private suite rentals Chicago
- Rentals with a fireplace Chicago
- Rentals with a patio Chicago
- Rentals with an accessible height bed Chicago
- Lakehouse rentals Chicago
- Fitness-friendly rentals Chicago
- Rentals with a washing machine and dryer Chicago
- Rentals with an EV charger Chicago
- Loft rentals Chicago
- Family-friendly rentals Chicago
- Kid-friendly rentals Chicago
- Rentals with lake access Chicago
- Rentals with a sauna Chicago
- Smoking-friendly rentals Chicago
- Rentals with a balcony Chicago
- Bed and breakfasts Chicago
- Townhouse rentals Chicago
- Apartment rentals Chicago
- Beachfront rentals Chicago
- Rentals with beach access Chicago
- Rentals with pools Chicago
- Boutique hotel rentals Chicago
- Condo rentals Chicago
- Rentals with a hot tub Chicago
- Waterfront rentals Chicago
- House rentals Chicago
- Pet-friendly rentals Chicago
- Mansion rentals Chicago
- Monthly Rentals Chicago
- Hotel rentals Downtown Chicago
- Boutique hotel rentals Downtown Chicago
- Hotel rentals Milwaukee
- Boutique hotel rentals Illinois
- Hotel rentals Illinois
- Boutique hotel rentals Cook County
- Hotel rentals Cook County
- 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