Hotel vacation 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.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Chicago hotel rentals
Family-friendly hotel rentals
Boutique hotel in Chicago
4.67 out of 5 average rating, 6 reviews1BD Suite @ The Guesthouse Hotel(2)
Hotel room in Uptown
4.98 out of 5 average rating, 44 reviews1 BD Luxury Boutique Apartment
Boutique hotel in Chicago
4.97 out of 5 average rating, 38 reviews1BD Suite @ The Guesthouse Hotel
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 Chicago
4.58 out of 5 average rating, 81 reviewsHotel Perks - Private Bedroom | Private Bathroom
Hotel room in Near North Side
4.4 out of 5 average rating, 30 reviewsHotel Perks - Private Bedroom | Private Bathroom
Hotel room in Chicago
4.48 out of 5 average rating, 3658 reviewsHotel Perks - Private Bedroom | Private Bathroom
Hotel rentals with a pool
Hotel in Westmont
4.5 out of 5 average rating, 46 reviewsKing Bed with a private tub (breakfast included)
Hotel in Near North Side
5.0 out of 5 average rating, 9 reviewsHaven of Serenity! Pets Allowed, Onsite Pool
Hotel in Chicago
5.0 out of 5 average rating, 4 reviewsComfort and Relaxation! Parking, Near Navy Pier
Hotel in Chicago
5.0 out of 5 average rating, 7 reviewsLight-flooded rooms and city views
Hotel in Schaumburg
4.0 out of 5 average rating, 4 reviews"Radisson Hotel Schaumburg"
Hotel in Chicago
120-yr-old landmark with floor-to-ceiling views
Hotel in Chicago
5.0 out of 5 average rating, 3 reviewsCozy Stay in River North! with Indoor Pool
Hotel in Chicago
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
ﺩ.ﺇ257 before taxes and fees
Destinations to explore
- Downtown Chicago Vacation rentals
- Milwaukee Vacation rentals
- Lake Geneva Vacation rentals
- Lake Michigan Beach Vacation rentals
- Saugatuck Vacation rentals
- Evanston Vacation rentals
- Holland Vacation rentals
- South Haven Vacation rentals
- Naperville Vacation rentals
- South Side Vacation rentals
- South Bend Vacation rentals
- New Buffalo Vacation rentals
- Hotel rentals United States
- Aparthotel rentals United States
- Boutique hotel rentals United States
- Bed and breakfasts Chicago
- Fitness-friendly rentals Chicago
- Rentals with an accessible height bed Chicago
- Rentals with a washer and dryer Chicago
- House rentals Chicago
- Smoking-friendly rentals Chicago
- Monthly Rentals Chicago
- Lakehouse rentals Chicago
- Rentals with lake access Chicago
- Guesthouse rentals Chicago
- Private suite rentals Chicago
- Boutique hotel rentals Chicago
- Rentals with pools Chicago
- Rentals with a patio Chicago
- Condo rentals Chicago
- Rentals with a hot tub Chicago
- Rentals with breakfast Chicago
- Rentals with a fire pit Chicago
- Rentals with a balcony Chicago
- Apartment rentals Chicago
- Waterfront rentals Chicago
- Rentals with an EV charger Chicago
- Rentals with a fireplace Chicago
- Rentals with a home theater Chicago
- Rentals with outdoor seating Chicago
- Townhouse rentals Chicago
- Beachfront rentals Chicago
- Family-friendly rentals Chicago
- Pet-friendly rentals Chicago
- Mansion rentals Chicago
- Rentals with a sauna Chicago
- Loft rentals Chicago
- Kid-friendly rentals Chicago
- Rentals with beach access Chicago
- Hotel rentals Downtown Chicago
- Boutique hotel rentals Downtown Chicago
- Hotel rentals Milwaukee
- Hotel rentals Illinois
- Boutique hotel rentals Illinois
- Hotel rentals Cook County
- Boutique 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