Find Chicago Hotels with Rooftop Pools

With a stay at DoubleTree by Hilton Chicago - Magnificent Mile in Chicago (Downtown Chicago), you'll be a 5-minute walk from Michigan Avenue and 14 minutes by foot from Millennium Park. This 4-star hotel is 0.6 mi (1 km) from Chicago Riverwalk and 1.1 mi (1.7 km) from Navy Pier. Be sure to enjoy recreational amenities including an outdoor pool and a fitness center. Additional amenities at this hotel include complimentary wireless Internet access, concierge services, and a television in a common area. Grab a bite to eat at HotHouse, a restaurant which features a bar/lounge, or stay in and take advantage of the room service. Quench your thirst with your favorite drink at the poolside bar. Full breakfasts are available daily from 7:00 AM to 10:00 AM for a fee. Featured amenities include complimentary wired Internet access, a business center, and express check-out. Planning an event in Chicago? This hotel has facilities measuring 16000 square feet (1486 square meters), including a conference center. Self parking (subject to charges) is available onsite. Make yourself at home in one of the 404 guestrooms featuring MP3 docking stations and LED televisions. Cable programming provides entertainment, and wired and wireless Internet access is available for a surcharge. Private bathrooms with shower/tub combinations feature complimentary toiletries and hair dryers. Conveniences include safes and desks, as well as phones with free local calls.

Holiday Inn & Suites Chicago-Downtown offers modern comfort with a boutique feel, thoughtful amenities, and a prime downtown location, providing the perfect gateway to the best of Chicago. Located just across from the iconic Old Post Office, our hotel offers seamless access to famous local attractions like the Willis Tower Skydeck, the United Center, Wrigley Field, and McCormick Place. Plus, enjoy proximity to major businesses and world-class dining. With 1,047 sq ft of flexible meeting space, we are the perfect spot for small meetings and corporate events. Enjoy breakfast at our on-site restaurant, stay active at our Fitness Center, and relax at our seasonal rooftop pool. From free Wi-Fi and on-site parking to a 24-hour Market for drinks, snacks, and essentials, we provide everything you need for an unforgettable stay in Chicago.

With a stay at The Hotel at Midtown in Chicago (Bucktown), you'll be within a 5-minute drive of Wrigley Field and Lake Michigan. This family-friendly hotel is 3.3 mi (5.3 km) from United Center and 3.9 mi (6.3 km) from Michigan Avenue. Pamper yourself with a visit to the spa, which offers massages and facials. You're sure to appreciate the recreational amenities, which include 2 hot tubs, indoor tennis courts, and a health club. Additional features at this hotel include complimentary wireless internet access, babysitting (surcharge), and a hair salon. Enjoy a meal at the restaurant or snacks in the hotel's coffee shop/cafe. Unwind at the end of the day with a drink at the bar/lounge or the poolside bar. Cooked-to-order breakfasts are available daily from 6 AM to 10 AM for a fee. Featured amenities include dry cleaning/laundry services, a 24-hour front desk, and multilingual staff. This hotel has 3 meeting rooms available for events. Make yourself at home in one of the 55 guestrooms featuring refrigerators and LED televisions. Complimentary wireless internet access keeps you connected, and satellite programming is available for your entertainment. Private bathrooms with bathtubs or showers feature rainfall showerheads and designer toiletries. Conveniences include laptop-compatible safes and desks, as well as phones with free local calls.

With a stay at Level Chicago Fulton Market, you'll be centrally located in Chicago, within a 5-minute drive of Chicago Riverwalk and Michigan Avenue. This hotel is 1.6 mi (2.5 km) from Millennium Park and 1.9 mi (3.1 km) from United Center. Take advantage of recreation opportunities such as a seasonal outdoor pool, or other amenities including complimentary wireless internet access and concierge services. This hotel also features a picnic area, gas grills, and a banquet hall. Featured amenities include a business center, a 24-hour front desk, and luggage storage. Self parking (subject to charges) is available onsite. Make yourself at home in one of the 57 individually decorated guestrooms, featuring kitchens with refrigerators and ovens. Your pillowtop bed comes with Egyptian cotton sheets. Rooms have private balconies or patios. Smart televisions with cable programming provide entertainment, while complimentary wireless internet access keeps you connected. Bathrooms have deep soaking bathtubs and rainfall showerheads.

With a stay at Level Chicago - River North, you'll be centrally located in Chicago, within a 5-minute drive of Michigan Avenue and Chicago Riverwalk. This hotel is 0.5 mi (0.8 km) from State Street and 1.3 mi (2.1 km) from Millennium Park. Don't miss out on the many recreational opportunities, including a fitness center, a seasonal outdoor pool, and bicycles to rent. This hotel also features complimentary wireless internet access, concierge services, and barbecue grills. Featured amenities include a 24-hour front desk, luggage storage, and laundry facilities. Self parking (subject to charges) is available onsite. Make yourself at home in one of the 99 individually furnished guestrooms, featuring kitchens with full-sized refrigerators/freezers and ovens. Your pillowtop bed comes with premium bedding. 50-inch flat-screen televisions with cable programming provide entertainment, while complimentary wireless internet access keeps you connected. Conveniences include safes and desks, as well as phones with free local calls.

Enjoy a premium location between the Magnificent Mile and Navy Pier when you stay at Hilton Grand Vacations Chicago Downtown/Magnificent Mile. Located on the top floor of the Doubletree, our vibrant hotel places you walking distance from top Chicago attractions. Savor delicious onsite dining, enjoy a workout in our state-of-the-art fitness center, or relax by our seasonal rooftop pool, complete with bar and terrace. Every spacious room and suite at our Downtown Chicago hotel features a comfortable couch, mini-fridge and 55" wall mounted HDTV. Upgrade to a suite for a living room with queen sofa bed, dining table with 4 chairs and wet bar. For cozy dining in the privacy of your room or suite, choose Room Service, available between 3pm and 11pm. Enjoy all the amenities you need to unwind or stay productive throughout your stay. Get work done in the 24-hour business center, swim in our seasonal pool, grab snacks in the lobby market, or work out in our modern fitness center. Enjoy warm, friendly dining at HotHouse restaurant, ideally located in the lobby. Fill up on a buffet breakfast, savor shareable plates, sliders, flatbreads, salads and desserts, then relax with Illinois craft beers and exceptional cocktails. Hosting an event near Hilton Grand Vacations Chicago Downtown/Magnificent Mile? Choose us as the overnight accommodation for you or your guests.

Located in Chicago (West Town), The Robey, Chicago, a Member of Design Hotels is within a 10-minute drive of Museum of Contemporary Art Chicago and Art Institute of Chicago. This hotel is 2.2 mi (3.5 km) from United Center and 3.2 mi (5.1 km) from Michigan Avenue. Don't miss out on recreational opportunities including a fitness center and a seasonal outdoor pool. Additional amenities at this Art Deco hotel include complimentary wireless internet access, concierge services, and complimentary use of a nearby fitness facility. For dinner or brunch, stop by Cafe Robey, a restaurant that specializes in American cuisine. Dining is also available at the coffee shop/cafe, and room service (during limited hours) is provided. Relax with a refreshing drink from the poolside bar or one of the 3 bars/lounges. Cooked-to-order breakfasts are available daily from 7:00 AM to 1:00 PM for a fee. Featured amenities include dry cleaning/laundry services, a 24-hour front desk, and multilingual staff. Planning an event in Chicago? This hotel has 1250 square feet (116 square meters) of space consisting of conference space and 2 meeting rooms. Make yourself at home in one of the 89 air-conditioned rooms featuring free minibar items and flat-screen televisions. Your bed comes with down comforters and premium bedding. Complimentary wireless internet access keeps you connected, and cable programming is available for your entertainment. Private bathrooms with showers feature designer toiletries and hair dryers.

Located in Chicago (Downtown Chicago), Level Chicago – Old Town is within a 15-minute walk of Lake Michigan and Michigan Avenue. This family-friendly aparthotel is 1.6 mi (2.5 km) from Chicago Riverwalk and 2 mi (3.2 km) from Millennium Park. Take advantage of recreational opportunities offered, including a 24-hour health club, a sauna, and a seasonal outdoor pool. Additional amenities at this aparthotel include complimentary wireless internet access, concierge services, and an arcade/game room. Enjoy a meal at Dialtone or snacks in the aparthotel's coffee shop/cafe. Featured amenities include a 24-hour business center, dry cleaning/laundry services, and a 24-hour front desk. Self parking (subject to charges) is available onsite. Make yourself at home in one of the 35 individually decorated guestrooms, featuring kitchens with full-sized refrigerators/freezers and ovens. Your pillowtop bed comes with premium bedding. Complimentary wireless internet access keeps you connected, and flat-screen televisions are provided for your entertainment. Conveniences include safes and desks, as well as phones with free local calls.

Located in Chicago (Downtown Chicago), Kasa River North Chicago is within a 15-minute walk of Michigan Avenue and State Street. This aparthotel is 0.7 mi (1.1 km) from Merchandise Mart and 1.1 mi (1.8 km) from Chicago Riverwalk. Enjoy recreational amenities such as a fitness center and a seasonal outdoor pool. Additional features at this aparthotel include concierge services and a communal living room. Featured amenities include a business center, express check-out, and an elevator. Make yourself at home in one of the 11 individually decorated guestrooms, featuring kitchens with full-sized refrigerators/freezers and ovens. Your room comes with a memory foam bed. 55-inch flat-screen televisions with digital programming provide entertainment, while complimentary wireless internet access keeps you connected. Conveniences include desks and microwaves.

With a stay at The Hoxton Chicago in Chicago (Downtown Chicago), you'll be within a 5-minute drive of Millennium Park and United Center. This hotel is 1.3 mi (2.1 km) from Chicago Riverwalk and 1.5 mi (2.5 km) from Michigan Avenue. Take advantage of recreation opportunities such as a seasonal outdoor pool, or other amenities including complimentary wireless internet access and discounted use of a nearby fitness facility. Enjoy Mediterranean cuisine at Cira, one of the hotel's 2 restaurants, or stay in and take advantage of the room service (during limited hours). Snacks are also available at the coffee shop/cafe. Relax with a refreshing drink from the poolside bar or one of the 3 bars/lounges. Featured amenities include complimentary newspapers in the lobby, dry cleaning/laundry services, and a 24-hour front desk. This hotel has 5 meeting rooms available for events. Make yourself at home in one of the 182 guestrooms featuring MP3 docking stations and LED televisions. Your pillowtop bed comes with down comforters and Egyptian cotton sheets. Complimentary wireless internet access is available to keep you connected. Private bathrooms with showers feature rainfall showerheads and designer toiletries.