11 Best Hotels in Chicago with Rooftop Pools

Welcome to a delightful oasis in the heart of Chicago! This historic hotel brings you a rooftop pool, perfect for soaking up the sun while enjoying stunning views of the city. Located near the famous Magnificent Mile, you’ll be surrounded by great shopping, dining, and entertainment options to make your stay even more enjoyable.

Each modern guest room at Viceroy Chicago is designed for relaxation with comfy seating, a flat-screen TV, and free Wi-Fi. Feeling hungry? Indulge in meals inspired by Midwest flavors at Somerset, or sip on crafted cocktails at the rooftop bar. Plus, if you’re in the mood to relax in the comfort of your room, in-room dining is just a phone call away!

When you’re not chilling by the pool, stay active at the fitness center or explore the nearby Oak Street Beach – it’s just a quick walk away! Whether you’re visiting for a vacation or a special event, this hotel is your go-to spot for a fun and memorable Chicago experience.

Welcome to Kasa River North Chicago, a fantastic spot for your next getaway! This hotel is in the heart of the city and offers a seasonal rooftop pool that's perfect for lounging under the sun while taking in the amazing skyline views. You'll also find a fitness center to keep you energized, and with free Wi-Fi, staying connected is a breeze!

Each room has everything you need to unwind after a day of exploring. Enjoy comfy beds, a flat-screen TV, and kitchen perks like a fridge and coffee machine. Some rooms even have a view of the bustling city below! You'll be close to all the excitement, with famous attractions like Water Tower Chicago and the Museum of Contemporary Art just around the corner.

At Kasa River North, you’ll experience the perfect blend of comfort, convenience, and fun. Enjoy your stay and make some unforgettable memories!

Nestled in the lively Wicker Park neighborhood, The Robey is a charming hotel with a rooftop pool that offers stunning views of Chicago’s skyline. It's a delightful place to relax after a day of sightseeing. Guests rave about the beautiful hardwood floors and cozy 400-thread count sheets in the bright and airy rooms. Plus, you can stay connected with free Wi-Fi and catch your favorite shows on the flat-screen TV.

Café Robey is the perfect spot for delicious meals, whether you're after breakfast, lunch, or dinner, alongside a refreshing drink on the second-floor lounge. Don’t forget to check out the rooftop lounge, Up & Up, where you can sip cocktails while soaking in breathtaking views of the city. Whether you're lounging by the pool or enjoying the local scene, The Robey offers a warm, fun atmosphere for your Chicago adventure!

The Royal Sonesta Chicago River North is a fab choice for anyone looking to splash around in a rooftop pool while soaking in some of the best views of the city. This 4-star boutique hotel brings a touch of personality with designs inspired by the iconic Chicago World’s Fair. The rooms are a treat, featuring comfy beds, large bathrooms with plush bathrobes, and a 37-inch flat-screen TV to keep you entertained. Trust us, it'll be your cozy retreat after a fun day out!

Kick-start your day with complimentary coffee and tea, or grab a delicious meal at nearby CBR, where you can enjoy everything from regional breakfast bites to weekend brunch. If you want to squeeze in some fitness, check out the 24-hour gym with all the modern equipment you need. Whether you’re splashing in the pool, chilling by the rooftop, or exploring the vibrant neighborhoods of Chicago, the Royal Sonesta gives you a taste of excitement and relaxation all in one spot!

If you're on the hunt for a fantastic hotel in Chicago with a rooftop pool, look no further than Hilton Grand Vacations Club Chicago Magnificent Mile! This place is all set to make your stay enjoyable with cozy air-conditioned rooms, a sparkling seasonal outdoor pool, and complimentary WiFi. The friendly staff is available 24/7, making it easy to get help whenever you need it. Plus, there's private parking available — just in case you’re driving.

Each room comes with a comfy seating area, a flat-screen TV, and a fridge to keep your snacks cool. If you're in the mood for a bite, their restaurant has a menu filled with delicious American cuisine, and you'll find options for vegetarian and gluten-free diets too! When you're ready for adventure, you'll be close to beautiful beaches and shopping spots, making it easy to explore the city's best offerings. Whether you're feeling energetic or just want to relax by the pool, Hilton Grand Vacations is a perfect base for your Chicago escapade!

If you're searching for a top-notch hotel in Chicago with a rooftop pool, check out Level Chicago Fulton Market! This fantastic spot boasts a seasonal outdoor swimming pool and super comfy rooms with free WiFi, making it perfect for unwinding after a day of exploring. The terrace is a wonderful place to relax, soak up the sun, and take in some lovely city views. With a friendly 24-hour front desk and convenient private parking, you’ll have all the support you need while enjoying your stay.

Just a hop away from some of Chicago's favorite landmarks like Shops at Northbridge and Willis Tower, this hotel positions you perfectly for adventures around the city. It’s all about having a great time while enjoying spacious digs, a refreshing dip in the pool, and access to yummy dining options nearby. Overall, Level Chicago is a fantastic choice for anyone eager to make the most of their time in the Windy City!

If you're on the lookout for a fabulous hotel in Chicago with a rooftop pool, the Hyatt House Chicago West Loop-Fulton Market is definitely worth checking out! This hotel creates a cheerful atmosphere with its cool indoor pool, a cozy terrace, and a lovely bar where you can kick back after a day of exploring. There’s even a fitness center to keep you energized! Guests rave about their comfy rooms which come with a fridge, a private bathroom, and all the essentials, ensuring a delightful stay.

Location-wise, you’re right in the heart of the action, close to some of Chicago’s iconic spots. You can easily make the most of your trip, whether it’s visiting local attractions or enjoying the vibrant culinary scene. With friendly service at the 24-hour front desk ready to chat, you can be sure your queries are taken care of, which adds to the charm of this lovely hotel. Enjoy your time in Chicago!

Welcome to DoubleTree by Hilton Chicago Magnificent Mile, a gem that brings you an awesome rooftop pool to soak up the sun right in the heart of downtown! With just a short stroll, you’ll find yourself surrounded by the excitement of the famous Magnificent Mile. Each room is not just modern, but also comes with a 50-inch flat-screen TV and a lovely little coffeemaker to start your mornings right. Plus, don’t forget to grab a warm chocolate chip cookie at check-in—it's a sweet little touch that makes you feel right at home!

When it comes to dining, HotHouse is your go-to spot! This open-concept restaurant serves up delicious breakfast and dinner options, along with a friendly environment to unwind and enjoy a cocktail after a busy day exploring the city. Easily reach Millennium Park for a fun day out or take a quick drive to admire the stunning views from Willis Tower. No matter what you choose to do, your stay here will be unforgettable!

Experience a fabulous stay at Homewood Suites by Hilton Chicago Downtown/Magnificent Mile! Perfectly located near the bustling Michigan Avenue, this hotel offers self-catering suites that feel like a home away from home. Each spacious suite features a full kitchen, complete with a 2-burner stove and dishwasher, making it super easy to whip up your favorite meals. And if you’re lucky, you might just snag a suite with breathtaking views of Lake Michigan and the iconic Chicago skyline!

With friendly staff available at the 24-hour front desk, you have everything you need for a smooth and enjoyable getaway. Plus, if you're up for some fun in the sun, the hotel provides a great spot to relax or take a quick stroll to enjoy the beach at Lake Michigan. Get ready for an unforgettable Chicago adventure!

Get ready for a fantastic time at the Hampton Inn & Suites Chicago Magnificent Mile, where a rooftop pool awaits your splash! This hotel is perfectly situated just steps away from the famous Magnificent Mile, giving you easy access to exciting shopping and dining spots. You can unwind in spacious guestrooms, all equipped with flat-screen TVs, fridges, and even a handy coffee maker. Little touches, like a work desk and hairdryer, make your stay extra cozy!

Everyone at the 24-hour front desk is super friendly and ready to help with anything you need. If laundry is on your to-do list, don’t worry; they’ve got you covered with laundry and dry-cleaning services, too. With all the city highlights just a short drive away, you’ll have the perfect base for exploring Millennium Park, the Art Institute, and more. Your Chicago adventure is calling, and the Hampton Inn & Suites is here to welcome you!

Looking for a fabulous hotel with a rooftop pool in Chicago? Check out this gem that puts you steps away from the hustle and bustle of the Magnificent Mile! It’s the perfect spot to soak up the sun while enjoying stunning views of the city skyline from their rooftop deck. Plus, you’ll find a cozy indoor heated pool just waiting for you after a day of exploring.

Inside your room at Best Western Chicago Downtown, you'll find all the comforts of home, including a flat-screen TV, a coffee maker, and plenty of space to unwind. When it’s time to refuel, head over to Pizzeria Ora Restaurant for some mouth-watering Chicago-style deep-dish pizza and delicious Italian dishes all day long. And if you're feeling lazy, dining in is a breeze with convenient in-room service!

With friendly staff available 24/7, you can relax and enjoy amenities like a fitness center and laundry services. This hotel truly offers a wonderful spot to create unforgettable memories in the Windy City!