With a mix of large scale skyscrapers and beautiful parks, Chicago is a great holiday destination. Although known as the windy city, you can rest assured that this doesn’t refer to the weather. On your first few days, if you want to sit and absorb the culture, you should head to the popular site of Millenium Park. With its grand open spaces, art and theatre and ice rink, you can easily spend a few hours here. For great views, head to the top of Willis building for panoramic cityscapes. For something a bit different, spend some time at the Navy Pier. This large pier has everything from fun rides, fantastic eateries and boutique shops. It’s a great place to take children for a day out. So after all that walking around and exploring, we’re sure that you’ll want to rest your feet and relax. Now you can sit back, or float in this case, and let the world pass you by. Just for you, we’ve found the best hotels with relaxing outdoor pools, in Chicago, Illinois. Keep reading and book today to get yourself in the vacation mood.
We handpicked these listings carefully, considering (wherever possible) recent guest reviews, location, accommodation type, prices, availability of dates, decor, and access to outdoor pool. The image galleries get refreshed with the latest updates regularly. They were last updated on August 23, 2024.
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1. Hampton Inn Chicago Magnificent Mile (from USD 231)
Looking for something more than a regular outside pool? Look no further than this hotel which features a rooftop pool. You can relax on the sundeck and take in the skyline views. Inside, the rooms are all equipped with satellite television, work desk, coffee machine and refrigerator. Additional hotel amenities include a modern fitness center, laundry facilities and an onsite pub-styled restaurant with a traditional menu. The property is just a short distance from the Water Tower Place, ideal for a quick shopping visit, and Millenium Park is also nearby.
Hampton Inn Chicago Downtown/Magnificent Mile This is a Proud Certified property where you can be extra sure of a welcoming stay.
Address: 160 East Huron Street
1.41 km (0.9 mi) from Millennium Park
2. Radisson Blu Aqua Hotel Chicago (from USD 588)
Reasonable pricing for a hotel in a prime downtown location.
Modern facilities including a spacious gym, outdoor pool, and spacious rooms with balconies.
Conveniently located near popular attractions such as Grant Park and Michigan Avenue, making it ideal for sightseeing.
Delicious dining options with a variety of choices, though some guests experienced slow service.
This boutique and stylish luxury hotel is located just a short five-minute walk away from Millenium Park and the Magnificent Mile. There is free WiFi in every room alongside a minibar, working area and a flat-screen cable television. The hotel is a perfect place for a business stay. In the morning, take a dip in the rooftop pool, relax in the sauna or workout on the outdoor track as part of the health club, which all guests have free access to. An onsite Italian restaurant caters for breakfast, lunch and dinner, alongside a cocktail bar.
Radisson Blu Aqua Hotel, Chicago This is a Proud Certified property where you can be extra sure of a welcoming stay.
Address: 221 North Columbus Drive
479 meters (0.3 ft) from Millennium Park
3. DoubleTree by Hilton Chicago - Magnificent Mile (from USD 304)
Atop this hotel, you’ll find a pleasant outdoor pool with surrounding sun lounge area. The rooms are decorated in a contemporary style and are very comfortable. Each includes a 50-inch flat screen television, iPod docking station and a coffee maker. Dining options onsite include an open-concept restaurant called HotHouse. It serves both an a la carte and traditional American menu. Guests can also take full advantage of the well-equipped fitness center. The property is within a five-minute walk of the famous Magnificent Mile.
DoubleTree by Hilton Chicago Magnificent Mile
Address: 300 East Ohio Street
1.15 km (0.8 mi) from Millennium Park
4. Hampton Inn Chicago Downtown/ Magnificient Mile (from USD 398)
On the 40th floor of this popular hotel, you’ll find the modern fitness center. Guests can also access the seasonal outdoor pool which has fantastic city views. This property is nestled in just one block from Michigan Avenue and so is an ideal holiday base. The suites all come equipped with a modern kitchen that includes a two-burner stove and dishwasher. Still, there is an onsite restaurant should you want a break from the cooking. Free breakfast is served daily in the hotel. You might also be tempted by the dinner and cocktails which are available in the on-site British-style pub.
Homewood Suites by Hilton Chicago Downtown - Magnificent Mile
Address: 152 East Huron Street
1.39 km (0.9 mi) from Millennium Park
5. Chicago Lake Shore Hotel (from USD 63)
We love that this hotel offers both free parking for guests and shuttle service, making getting around much easier. Located on the shore of Lake Michigan, this property also boasts an outdoor swimming pool which is great for a dip in the afternoon sun. Each of the rooms is well-equipped with a 37-inch flat-screen television, coffee facilities and free WiFi. There is a cafe on the property which serves American cuisine and on Friday evenings, live jazz music is performed.
Chicago Lake Shore Hotel
Address: 4900 SOUTH LAKE SHORE DRIVE, Hyde Park, Chicago (IL), United States, 60615
9.05 km (5.7 mi) from Millennium Park
6. The Robey (from USD 365)
Reasonable rates for chic, stylish rooms in a prime city location.
Rooftop bar, cafe, and pool with stunning views. Complimentary beers and discounts for hotel guests.
Conveniently located in the vibrant Wicker Park neighborhood, near public transportation and local attractions.
Excellent dining options including a great brunch, rooftop bar, and complimentary afternoon treats.
Just 3 miles (4.8 km) from local amenities such as shopping, eateries and entertainment at the famous Magnificent Mile, this hotel is a great holiday base. With an outdoor seasonal pool, full WiFi, beautiful furnishings and excellent customer service, we know that you’ll have a great time. The bright and spacious bedrooms have hardwood floors, flat-screen television and even a Bluetooth-enabled sound system. There are two dining options onsite; Cafe Robey has a French-American menu while the rooftop lounge Up & Up boasts fantastic views and delicious cocktails.
The Robey, Chicago, a Member of Design Hotels
Address: 2018 W North Avenue
5.55 km (3.5 mi) from Millennium Park
7. Viceroy Chicago (from USD 840)
Enjoy panoramic city views and a cocktail while relaxing in the seasonal outdoor rooftop pool. This grand hotel has many different rooms, including a penthouse, so be sure to check out all of the in-room amenities before you book. In general, each guestroom is provided with a flat-screen television, a seating area, minibar, full WiFi and coffee machine. A mid-western style breakfast is served at Somerset, small plates and cocktails are delivered at Devereaux, the rooftop bar, and 24-hour room service is available.
Viceroy Chicago This is a Proud Certified property where you can be extra sure of a welcoming stay.
Address: 1118 North State Street
2.27 km (1.5 mi) from Millennium Park
8. Holiday Inn Hotel & Suites Chicago-Downtown (from USD 431)
With modern fitness facilities, this hotel also has a seasonal outdoor swimming pool which is ideal for relaxing in after a busy day exploring. The well-equipped rooms each have a comfortable bed, writing desk, seating area and a flat-screen television. In the suites, the seating area and work desk are separate from the bedroom area, so there is much more space. Check online to decide which room style best suits your needs. Alongside the pool and fitness center, additional onsite facilities include Sunny’s Restaurant and Lounge, darts, billiards, bicycles and more. Some of the additional features may come at a charge.
Holiday Inn Hotel & Suites Chicago - Downtown, an IHG Hotel This is a Proud Certified property where you can be extra sure of a welcoming stay.
Address: 506 West Harrison
1.7 km (1.1 mi) from Millennium Park
Don't forget the sunscreen
For us, having access to an outdoor pool always adds a sense of added luxury and fun. We love that the outdoor pools on our list also come with fantastic views, and in some cases, fantastic cocktails too. So, be sure to have your Instagram ready and let’s make your friends jealous. Simply book today, pack your suntan lotion, maybe a good book and let’s head out there.
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10 Best Hotels With Rooftop Pools in Chicago, ILChia Han Keong -
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