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
Boutique hotel in Andersonville
4.67 out of 5 average rating, 6 reviews1BD Suite @ The Guesthouse Hotel(2)
Boutique hotel in Chicago
4.97 out of 5 average rating, 38 reviews1BD Suite @ The Guesthouse Hotel
Hotel room in Uptown
4.98 out of 5 average rating, 44 reviews1 BD Luxury Boutique Apartment
Aparthotel in Chicago
4.85 out of 5 average rating, 20 reviews2BD Suite @The Guesthouse Hotel (2)
Hotel room in Chicago
4.91 out of 5 average rating, 34 reviews2BD/2BA Luxury Apartment - Roof Deck Access
Shared hotel room in Near North Side
4.58 out of 5 average rating, 81 reviewsHotel Perks - Private Bedroom | Private Bathroom
Hotel room in Near North Side
4.47 out of 5 average rating, 3649 reviewsHotel Perks - Private Bedroom | Private Bathroom
Hotel room in Chicago
4.47 out of 5 average rating, 15 reviewsHotel Perks - Private Bedroom | Private Bathroom
Hotel rentals with a pool
Hotel in Chicago
4.63 out of 5 average rating, 35 reviewsJust a short walk from Magnificent Mile! Pool!
Hotel in Westmont
4.55 out of 5 average rating, 44 reviewsKing Bed with a private tub (breakfast included)
Hotel in Near North Side
5.0 out of 5 average rating, 6 reviewsHaven of Serenity! Pets Allowed, Onsite Pool
Hotel in Chicago
5.0 out of 5 average rating, 7 reviewsLight-flooded rooms and city views
Hotel in Chicago
5.0 out of 5 average rating, 4 reviewsComfort and Relaxation! Parking, Near Navy Pier
Hotel in Schaumburg
3.67 out of 5 average rating, 3 reviews"Radisson Hotel Schaumburg"
Hotel in Gold Coast
120-yr-old landmark with floor-to-ceiling views
Hotel in River North
4.5 out of 5 average rating, 4 reviewsA short drive to Willis Tower! 2 Comfortable Units
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
€ 65 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
- Aparthotel rentals United States
- Boutique hotel rentals United States
- Hotel rentals United States
- Loft rentals Chicago
- Private suite rentals Chicago
- Fitness-friendly rentals Chicago
- Rentals with a patio Chicago
- Smoking-friendly rentals Chicago
- Family-friendly rentals Chicago
- Lakehouse rentals Chicago
- Rentals with a balcony Chicago
- Rentals with a washing machine and dryer Chicago
- Rentals with an accessible-height bed Chicago
- Rentals with a sauna Chicago
- Rentals with a fireplace Chicago
- Waterfront rentals Chicago
- Rentals with a cinema Chicago
- Rentals with outdoor seating Chicago
- Family-friendly rentals Chicago
- Mansion rentals Chicago
- Rentals with an EV charger Chicago
- Flat rentals Chicago
- Rentals with beach access Chicago
- Rentals with breakfast Chicago
- Rentals with a firepit Chicago
- Beachfront rentals Chicago
- Rentals with lake access Chicago
- Apartment rentals Chicago
- Rentals with a hot tub Chicago
- Pet-friendly rentals Chicago
- Bed and breakfasts Chicago
- Monthly Rentals Chicago
- Rentals with pools Chicago
- Guest house rentals Chicago
- Townhouse rentals Chicago
- Boutique hotel rentals Chicago
- House 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