Hotel holiday rentals in Downtown Chicago
Find and book unique hotels on Airbnb
Top-rated hotels in Downtown 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 Downtown Chicago hotels
Family-Friendly hotels
Boutique hotel in Uptown
4.97 out of 5 average rating, 38 reviews1BD/1BA Suite with Full Kitchen, Balcony w/ Grill
Hotel room in Uptown
4.98 out of 5 average rating, 44 reviews1BD/1BA Boutique Suite Near Wrigley, Uptown
Aparthotel in Uptown
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
4.91 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 Near North Side
4.47 out of 5 average rating, 15 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
Hotels 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
4.71 out of 5 average rating, 7 reviewsRelax and Unwind! Close to Water Tower Chicago!
Hotel in Streeterville
5.0 out of 5 average rating, 5 reviewsComfort and Relaxation! Parking, Near Navy Pier
Hotel in West Loop
5.0 out of 5 average rating, 8 reviewsLight-flooded rooms and city views
Hotel in Chicago
4.5 out of 5 average rating, 6 reviewsLarge Unit Close to the Millennium Park! Parking!
Hotel in Gold Coast
120-yr-old landmark with floor-to-ceiling views
Hotel in Near North Side
4.83 out of 5 average rating, 12 reviewsHaven of Serenity! Pets Allowed, Onsite Pool
Hotel in River North
4.58 out of 5 average rating, 40 reviewsJust a short walk from Magnificent Mile! Pool!
Destinations to explore
- 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
- Chicago Holiday rentals
- Aparthotel rentals United States
- Boutique hotel rentals United States
- Hotel rentals United States
- Boutique hotel rentals Chicago
- Hotel rentals Chicago
- Smoking-friendly rentals Downtown Chicago
- House rentals Downtown Chicago
- Family-friendly rentals Downtown Chicago
- Rentals with a patio Downtown Chicago
- Kid-friendly rentals Downtown Chicago
- Townhouse rentals Downtown Chicago
- Beachfront rentals Downtown Chicago
- Rentals with a hot tub Downtown Chicago
- Rentals with a washing machine and dryer Downtown Chicago
- Apartment rentals Downtown Chicago
- Rentals with breakfast Downtown Chicago
- Fitness-friendly rentals Downtown Chicago
- Condo rentals Downtown Chicago
- Loft rentals Downtown Chicago
- Rentals with an EV charger Downtown Chicago
- Rentals with pools Downtown Chicago
- Rentals with a sauna Downtown Chicago
- Rentals with a home theatre Downtown Chicago
- Rentals with beach access Downtown Chicago
- Rentals with a fire pit Downtown Chicago
- Waterfront rentals Downtown Chicago
- Monthly Rentals Downtown Chicago
- Rentals with a fireplace Downtown Chicago
- Pet-friendly rentals Downtown Chicago
- Boutique hotel rentals Downtown Chicago
- Rentals with lake access Downtown Chicago
- Rentals with outdoor seating 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