Top Hotels in Chicago with Outdoor Pools and Stunning Views

Chicago, a city renowned for its stunning architecture, vibrant culture, and world-class cuisine, offers an unforgettable experience for every traveler. When planning your visit, selecting the right accommodation is crucial to ensuring a memorable stay. For those seeking a blend of luxury, relaxation, and breathtaking scenery, hotels with outdoor pools and stunning views are an ideal choice. This guide will explore some of the top hotels in Chicago that offer these coveted amenities, providing you with detailed insights into their features, benefits, and why they deserve a place on your shortlist.

Why Choose a Hotel with an Outdoor Pool in Chicago?

Chicago summers are legendary. After a long winter, the city comes alive with outdoor events, festivals, and a general sense of joie de vivre. A hotel with an outdoor pool allows you to fully embrace this vibrant atmosphere, providing a refreshing oasis where you can unwind and soak up the sun. Beyond the simple pleasure of swimming, outdoor pools often offer additional benefits:

• Relaxation and Rejuvenation: Escape the hustle and bustle of the city with a tranquil poolside experience.
• Socializing: Many hotel pools feature poolside bars and lounges, perfect for mingling with other guests and enjoying refreshing cocktails.
• Family Fun: Hotels with outdoor pools are a great option for families, providing a dedicated space for kids to splash and play.
• Unique Perspective: Outdoor pools often offer stunning views of the city skyline or Lake Michigan, adding an extra layer of enjoyment to your swim.

Factors to Consider When Choosing a Hotel

Before diving into our list of top hotels, it’s essential to consider the factors that are most important to you. Here are a few key aspects to keep in mind:

• Location: Do you prefer to be in the heart of downtown, close to major attractions and shopping districts? Or would you rather stay in a quieter neighborhood with a more residential feel?
• Budget: Chicago offers a wide range of hotels, from budget-friendly options to ultra-luxurious resorts. Determine your budget beforehand to narrow down your choices.
• Amenities: Consider the amenities that are essential to your stay. Do you need a fitness center, spa, on-site dining, or business facilities?
• Pool Features: Not all outdoor pools are created equal. Some offer stunning views, while others have dedicated children’s areas or poolside bars.
• Reviews: Read reviews from other travelers to get an unbiased perspective on the hotel’s quality and service.

Top Hotels in Chicago with Outdoor Pools and Stunning Views

The Peninsula Chicago

Located in the heart of the Magnificent Mile, The Peninsula Chicago is synonymous with luxury and impeccable service. Its stunning rooftop terrace features a half-Olympic length swimming pool, offering breathtaking views of the city skyline. The pool area is beautifully landscaped and features comfortable lounge chairs, umbrellas, and a poolside bar serving refreshing drinks and light snacks. The Peninsula Chicago is consistently ranked among the best hotels in the world, and its outdoor pool is just one of the many reasons why.

Key Features:

• Half-Olympic length swimming pool
• Stunning rooftop views
• Poolside bar and lounge
• Luxurious accommodations
• World-class dining options
• Exceptional service

Why Choose The Peninsula Chicago?

If you’re looking for the ultimate in luxury and sophistication, The Peninsula Chicago is an excellent choice. The hotel’s impeccable service, stunning accommodations, and breathtaking rooftop pool make it a truly unforgettable experience. The location on the Magnificent Mile also provides easy access to the city’s best shopping, dining, and entertainment.

Thompson Chicago

Situated in the vibrant Gold Coast neighborhood, the Thompson Chicago offers a stylish and sophisticated experience. Its rooftop pool provides stunning views of Lake Michigan and the city skyline. The pool area is designed with a modern aesthetic, featuring comfortable lounge chairs, cabanas, and a bar serving handcrafted cocktails. The Thompson Chicago is a popular choice for both business and leisure travelers, thanks to its convenient location and exceptional amenities.

Key Features:

• Rooftop pool with Lake Michigan views
• Modern and stylish design
• Poolside bar and cabanas
• Convenient location in the Gold Coast
• Exceptional dining options
• Comfortable and well-appointed rooms

Why Choose Thompson Chicago?

The Thompson Chicago is a great option for travelers who appreciate modern design, stunning views, and a convenient location. The rooftop pool is a particular highlight, offering a relaxing and stylish escape from the city. The hotel’s proximity to the Gold Coast’s shops, restaurants, and nightlife also makes it an ideal base for exploring the area.

Soho House Chicago

Located in the West Loop neighborhood, Soho House Chicago is a private members’ club and hotel that offers a unique and exclusive experience. Its rooftop pool is a popular spot for members and hotel guests alike, offering stunning views of the city skyline. The pool area features a relaxed and bohemian atmosphere, with comfortable lounge chairs, umbrellas, and a bar serving refreshing drinks and snacks. Soho House Chicago is a great option for travelers who are looking for a more intimate and stylish experience.

Key Features:

• Rooftop pool with city skyline views
• Relaxed and bohemian atmosphere
• Poolside bar and lounge
• Private members’ club and hotel
• Located in the trendy West Loop
• Unique and exclusive experience

Why Choose Soho House Chicago?

Soho House Chicago is a great choice for travelers who are looking for a more unique and exclusive experience. The rooftop pool is a particular highlight, offering stunning views and a relaxed atmosphere. The hotel’s location in the trendy West Loop also provides easy access to some of the city’s best restaurants, bars, and art galleries.

The Robey

Situated in the Wicker Park neighborhood, The Robey is a boutique hotel that offers a stylish and affordable option. Its rooftop pool provides stunning views of the city skyline and the surrounding neighborhood. The pool area features a retro-chic design, with colorful lounge chairs, umbrellas, and a bar serving handcrafted cocktails. The Robey is a popular choice for travelers who are looking for a trendy and budget-friendly option.

Key Features:

• Rooftop pool with city skyline views
• Retro-chic design
• Poolside bar and lounge
• Boutique hotel in Wicker Park
• Affordable and stylish
• Close to local shops and restaurants

Why Choose The Robey?

The Robey is a great choice for travelers who are looking for a trendy and affordable option. The rooftop pool is a particular highlight, offering stunning views and a retro-chic atmosphere. The hotel’s location in the vibrant Wicker Park neighborhood also provides easy access to local shops, restaurants, and bars.

The Langham, Chicago

Located in a landmark building designed by Mies van der Rohe, The Langham, Chicago, exudes sophistication and elegance. The hotel features a stunning indoor pool with floor-to-ceiling windows offering panoramic views of the city. While not strictly an outdoor pool, the expansive views and luxurious atmosphere provide a similar sense of relaxation and escape. The pool area includes comfortable lounge chairs, a whirlpool, and access to the Chuan Spa.

Key Features:

• Stunning indoor pool with city views
• Luxurious and elegant design
• World-class dining options
• Chuan Spa access
• Exceptional service
• Located in a landmark building

Why Choose The Langham, Chicago?

While the Langham doesn’t have an outdoor pool, its indoor pool provides a comparable experience with breathtaking views and a luxurious atmosphere. The hotel’s exceptional service, world-class dining, and stunning architecture make it a truly memorable stay. The location in the heart of downtown also offers convenient access to major attractions and business districts.

The Hotel Lincoln

Overlooking Lincoln Park and Lake Michigan, The Hotel Lincoln offers a unique and charming experience. The hotel’s rooftop bar, J. Parker, boasts stunning panoramic views of the city skyline and lake. While not a traditional swimming pool, J. Parker features a splash pool, perfect for cooling off on a hot summer day while enjoying the breathtaking scenery. The hotel’s quirky and artistic design adds to its overall appeal.

Key Features:

• Rooftop bar with panoramic views
• Splash pool for cooling off
• Quirky and artistic design
• Overlooking Lincoln Park and Lake Michigan
• Close to local attractions
• Vibrant and energetic atmosphere

Why Choose The Hotel Lincoln?

The Hotel Lincoln is a great option for travelers who are looking for a unique and charming experience. The rooftop bar and splash pool offer stunning views and a fun atmosphere. The hotel’s location overlooking Lincoln Park and Lake Michigan also provides easy access to outdoor activities and local attractions.

Waldorf Astoria Chicago

The Waldorf Astoria Chicago, located in the Gold Coast, epitomizes timeless elegance and exceptional service. While it doesn’t offer an outdoor pool, its indoor lap pool is a sanctuary of tranquility. The pool area is beautifully designed with natural light and features comfortable lounge chairs and access to the hotel’s spa. The Waldorf Astoria Chicago is known for its impeccable attention to detail and commitment to providing a luxurious experience.

Key Features:

• Luxurious indoor lap pool
• Elegant and sophisticated design
• World-class dining options
• Exceptional spa services
• Impeccable service
• Located in the prestigious Gold Coast

Why Choose Waldorf Astoria Chicago?

Although the Waldorf Astoria Chicago doesn’t have an outdoor pool, its indoor pool offers a luxurious and relaxing experience. The hotel’s impeccable service, elegant design, and world-class amenities make it a truly unforgettable stay. The location in the Gold Coast also provides easy access to upscale shopping, dining, and cultural attractions.

Four Seasons Hotel Chicago

Perched above the Magnificent Mile, the Four Seasons Hotel Chicago offers breathtaking views of Lake Michigan and the city skyline. Its indoor pool, located on the spa level, provides a serene and luxurious escape. The pool area features comfortable lounge chairs, a whirlpool, and access to the hotel’s renowned spa. The Four Seasons Hotel Chicago is known for its exceptional service and commitment to providing a memorable experience for every guest.

Key Features:

• Indoor pool with stunning views
• Luxurious and serene atmosphere
• World-class dining options
• Exceptional spa services
• Impeccable service
• Located above the Magnificent Mile

Why Choose Four Seasons Hotel Chicago?

While the Four Seasons Hotel Chicago doesn’t have an outdoor pool, its indoor pool offers a luxurious and relaxing experience with breathtaking views. The hotel’s exceptional service, world-class dining, and prime location make it an ideal choice for discerning travelers.

The Gwen, a Luxury Collection Hotel, Chicago

Located in a historic building near the Magnificent Mile, The Gwen offers a unique and stylish experience. Its rooftop terrace features a heated outdoor pool that is open year-round, providing stunning views of the city skyline. The pool area is designed with a modern aesthetic, featuring comfortable lounge chairs, umbrellas, and a bar serving handcrafted cocktails. The Gwen is a popular choice for both business and leisure travelers, thanks to its convenient location and exceptional amenities.

Key Features:

• Heated outdoor pool open year-round
• Stunning rooftop views
• Modern and stylish design
• Poolside bar and lounge
• Convenient location near the Magnificent Mile
• Exceptional dining options

Why Choose The Gwen?

The Gwen is a great option for travelers who appreciate modern design, stunning views, and a convenient location. The heated outdoor pool is a particular highlight, offering a relaxing escape from the city year-round. The hotel’s proximity to the Magnificent Mile’s shops, restaurants, and attractions also makes it an ideal base for exploring the area.

Tips for Enjoying Your Hotel Pool Experience

To make the most of your hotel pool experience in Chicago, consider these tips:

• Check the pool hours: Make sure the pool is open during the times you plan to use it.
• Bring sunscreen: Protect your skin from the sun, especially during peak hours.
• Stay hydrated: Drink plenty of water or refreshing beverages to avoid dehydration.
• Follow pool rules: Adhere to the hotel’s pool rules to ensure a safe and enjoyable experience for everyone.
• Respect other guests: Be mindful of noise levels and avoid disruptive behavior.
• Consider the time of day: The pool may be less crowded during off-peak hours, such as early morning or late afternoon.
• Take advantage of poolside amenities: Many hotels offer poolside bars, lounges, and food service.

Beyond the Pool: Exploring Chicago

While relaxing by the pool is a great way to unwind, don’t forget to explore all that Chicago has to offer. Here are a few must-see attractions:

• Millennium Park: Home to Cloud Gate (The Bean), Crown Fountain, and Lurie Garden.
• Art Institute of Chicago: One of the world’s leading art museums, with a diverse collection spanning centuries and cultures.
• Navy Pier: A vibrant entertainment destination with rides, restaurants, shops, and stunning views of Lake Michigan.
• Magnificent Mile: A world-renowned shopping district with luxury boutiques, department stores, and restaurants.
• Wrigleyville: Home to Wrigley Field, the iconic ballpark of the Chicago Cubs.
• Museum Campus: A collection of world-class museums, including the Field Museum, Shedd Aquarium, and Adler Planetarium.
• Riverwalk: A scenic walkway along the Chicago River, with restaurants, bars, and boat tours.

Conclusion

Chicago offers a wealth of options for travelers seeking hotels with outdoor pools and stunning views. From the luxurious Peninsula Chicago to the trendy Robey, there’s a hotel to suit every taste and budget. By considering the factors outlined in this guide and exploring the top hotels we’ve highlighted, you can find the perfect accommodation for your Chicago getaway. Remember to book in advance, especially during peak season, to secure your preferred room and ensure a memorable experience in the Windy City. Whether you’re looking to relax by the pool, explore the city’s attractions, or simply enjoy the breathtaking views, Chicago has something to offer everyone.