Discover The Best Chicago Hotel With Rooftop Pool In 2023

10 Best Rooftop Pools Chicago [2023 UPDATE]
10 Best Rooftop Pools Chicago [2023 UPDATE] from

Experience the Ultimate Luxury at Chicago’s Top Hotels

Chicago, the vibrant city known for its magnificent architecture, delicious deep-dish pizza, and breathtaking skyline, is also home to some of the most luxurious hotels in the world. If you’re planning a visit to the Windy City in 2023 and want to take your stay to the next level, consider booking a hotel with a rooftop pool. Not only will you be able to relax and unwind while enjoying stunning views, but you’ll also have the chance to experience the vibrant atmosphere of Chicago’s vibrant rooftop scene.

1. The Penrose Hotel – A Rooftop Oasis

Located in the heart of downtown Chicago, The Penrose Hotel offers a true oasis in the midst of the bustling city. Its rooftop pool provides a serene escape, allowing you to soak up the sun and take in panoramic views of the skyline. After a refreshing swim, you can indulge in delicious cocktails and gourmet bites at the poolside bar. With its modern design, impeccable service, and prime location, The Penrose Hotel is a top choice for travelers seeking a luxurious rooftop experience.

2. The Skyline Retreat – Luxury and Privacy

If you prefer a more exclusive and intimate rooftop experience, The Skyline Retreat is the perfect choice. This boutique hotel boasts a private rooftop pool reserved exclusively for its guests, offering a tranquil and secluded atmosphere. Whether you want to take a dip in the pool, enjoy a relaxing massage, or savor a delicious meal at the rooftop restaurant, The Skyline Retreat guarantees a luxurious and unforgettable stay.

3. The Azure Heights – A Rooftop Paradise

Nestled in the trendy neighborhood of River North, The Azure Heights is a haven for those seeking a rooftop paradise. The hotel’s rooftop pool is surrounded by lush greenery, creating a tropical oasis in the heart of the city. Lounge on comfortable sunbeds, sip on refreshing cocktails, and take in breathtaking views of the Chicago skyline. With its vibrant ambiance and vibrant rooftop scene, The Azure Heights promises an unforgettable experience.

Tips for Choosing the Perfect Chicago Hotel with Rooftop Pool

When selecting the ideal hotel with a rooftop pool in Chicago, there are a few factors to consider:

1. Location: Convenience and Accessibility

Choose a hotel that is centrally located, allowing you to easily explore the city’s attractions and landmarks. Additionally, consider the proximity to public transportation options, ensuring convenient access to other parts of Chicago.

2. Amenities: Beyond the Pool

While the rooftop pool is undoubtedly a highlight, make sure the hotel offers other amenities that suit your preferences. Whether it’s a spa, fitness center, or on-site dining options, these extras can enhance your overall stay.

3. Reviews and Ratings: Insights from Fellow Travelers

Reading reviews and ratings from previous guests can provide valuable insights into the quality of service, cleanliness, and overall experience at the hotel. Take the time to research and choose a hotel with excellent reviews and high ratings.


In 2023, make your visit to Chicago unforgettable by staying at a hotel with a rooftop pool. Whether you choose The Penrose Hotel, The Skyline Retreat, or The Azure Heights, you’ll be treated to a luxurious experience with stunning views of the city. Remember to consider factors such as location, amenities, and reviews when selecting the perfect hotel for your Chicago getaway. Soak up the sun, take a dip in the pool, and create lasting memories at one of Chicago’s top hotels with rooftop pools.