Hotel holiday rentals in Chicago
Find and book unique hotel rentals on Airbnb
Top-rated hotel rentals in Chicago
Guests agree: these hotel rentals 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 hotel rentals in Chicago
Family-friendly hotel rentals
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
Hotel room in Uptown
4.91 out of 5 average rating, 34 reviews2BD/2BA Near Concert Venues, Wrigley Field
Boutique hotel in Uptown
4.97 out of 5 average rating, 38 reviews1BD/1BA Suite with Full Kitchen, Balcony w/ Grill
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, 3682 reviewsHotel Perks - Private Bedroom | Private Bathroom
Hotel room in Near North Side
4.47 out of 5 average rating, 15 reviewsHotel Perks - Private Bedroom | Private Bathroom
Hotel rentals with a pool
Hotel in Westmont
4.49 out of 5 average rating, 47 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 West Loop
5.0 out of 5 average rating, 9 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 Chicago
120-yr-old landmark with floor-to-ceiling views
Hotel in Chicago
4.58 out of 5 average rating, 40 reviewsJust a short walk from Magnificent Mile! Pool!
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
£55 before taxes and fees
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
- Boutique hotel rentals United States
- Hotel rentals United States
- Aparthotel rentals United States
- Private suite rentals Chicago
- Rentals with a fireplace Chicago
- Rentals with a cinema Chicago
- Rentals with outdoor seating Chicago
- Rentals with a washing machine and dryer Chicago
- Rentals with pools Chicago
- Rentals with lake access Chicago
- Waterfront rentals Chicago
- House rentals Chicago
- Smoking-friendly rentals Chicago
- Pet-friendly rentals Chicago
- Rentals with beach access Chicago
- Rentals with an EV charger Chicago
- Monthly Rentals Chicago
- Rentals with a patio Chicago
- Rentals with breakfast Chicago
- Rentals with a firepit Chicago
- Rentals with a balcony Chicago
- Flat rentals Chicago
- Townhouse rentals Chicago
- Lakehouse rentals Chicago
- Bed and breakfasts Chicago
- Loft rentals Chicago
- Apartment rentals Chicago
- Rentals with a hot tub Chicago
- Rentals with an accessible-height bed Chicago
- Family-friendly rentals Chicago
- Fitness-friendly rentals Chicago
- Beachfront rentals Chicago
- Boutique hotel rentals Chicago
- Rentals with a sauna Chicago
- Family-friendly rentals Chicago
- Mansion rentals Chicago
- Boutique hotel rentals Downtown Chicago
- 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