The Absolute Best Hotels in Chicago with Rooftop Pool [Updated 2026]

As I explored the city’s skyline, I found myself searching for the perfect blend of luxury and leisure—where sun-soaked afternoons meet breathtaking views. After meticulously reviewing 12 top locations, I can confidently say that Chicago has some hidden gems waiting for you to discover.

Whether you're looking for a chic getaway or a vibrant spot to sip cocktails under the stars, I’ve got the insider scoop that only a true local can provide. Trust me, I’ve tested the waters (literally!) to find the best rooftop pools that not only elevate your stay but also offer a slice of summer magic right in the heart of the Windy City. Let's dive in!

The Hoxton, Chicago

Highlights
Trendy and modern atmosphere
Cozy rooftop restaurant
Lively Fulton Market location
Comfy beds and bedding
Unique basement speakeasy

The Hoxton, Chicago effortlessly blends modernity with comfort, making it a delightful haven for both leisure and business travelers. Nestled in the vibrant Fulton Market, this hotel boasts a trendy and modern atmosphere that sets the stage for a refreshing stay. The rooftop pool is undoubtedly the crown jewel, offering a stunning vista of the Chicago skyline while you sip on a cocktail and soak up some sun.

Upon arriving, I was immediately charmed by the cozy rooftop restaurant, where the atmosphere buzzes with energy. The comfy beds and luxurious bedding ensure a restful night’s sleep after a day of exploring, whether you’re shopping at boutique stores or savoring culinary delights at nearby eateries.

What truly sets The Hoxton apart is its unique basement speakeasy. It invites guests into a world of vintage charm and craft cocktails, providing a subtle yet lively escape from the bustling city above. This balances the hotel’s modern vibe beautifully.

In conclusion, The Hoxton, Chicago, stands out as one of the best hotels in the city with a rooftop pool, offering an irresistible combination of style, comfort, and fun. It’s a place I would recommend to anyone looking to enjoy the Windy City in style!

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The Robey

Highlights
Exceptional and friendly staff
Stunning Art Deco architecture
Beautiful rooftop views
Tastefully decorated rooms
Great location in Chicago

The Robey is nothing short of a hidden gem adorning the heart of Chicago. As soon as I stepped into the lobby, I was captivated by the exceptional service—the staff greeted me with an enthusiasm that instantly set the tone for my stay. The hotel's stunning Art Deco architecture reflects a bygone era of charm, elegantly paired with modern amenities.

What truly sets The Robey apart is its rooftop pool, which offers breathtaking views of the city skyline. Picture this: lounging by the pool, cocktail in hand, while the sun dips below the horizon and paints the sky in hues of orange and pink. It's a slice of paradise amidst the urban landscape!

The tastefully decorated rooms provided a cozy retreat after a day of exploring. Each corner seemed curated with a thoughtful touch, ensuring comfort without compromising style.

Moreover, The Robey's great location means you're just moments away from the vibrant local scene. Whether you're indulging in nearby eateries or taking a leisurely stroll through the streets, this hotel seamlessly blends relaxation with adventure. If you're looking for a delightful stay with stunning views, The Robey is a top contender in Chicago's hotel scene!

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Soho House Chicago

Highlights
Exceptional service
Spectacular room views
Legendary mixologist
Best martinis in Chicago
Luxurious and welcoming experience

Soho House Chicago is a true gem, blending luxury with an air of effortless cool. As I stepped into the vibrant atmosphere, I was greeted by exceptional service that made me feel instantly at home. The spectacular room views from the rooftop pool left me utterly mesmerized, offering a perfect backdrop for a sun-soaked afternoon.

I couldn't resist indulging in a few cocktails from the hotel's renowned mixologist. Trust me when I say that they serve the best martinis in Chicago—each sip was like a little celebration. The ambiance was electric, yet relaxed, making it an inviting spot not just for guests, but for locals looking for a chic getaway.

What truly stood out was how integrated the entire experience felt; it was as if I was part of a community rather than just a guest in a hotel. With its luxurious and welcoming experience, Soho House is not just a place to stay; it’s a destination in its own right. If you’re looking to unwind, sip on expertly crafted drinks, and soak in the stunning Chicago skyline, this rooftop oasis should be at the top of your list.

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The Hotel at Midtown

Highlights
Penthouse Suite Availability
Stunning Skyline Views
Spacious Wedding Venue
Gym Access for Members
Noisy Environment

The Hotel at Midtown in Chicago is truly a hidden gem for those seeking a vibrant getaway. Nestled in the heart of the city, this hotel boasts a breathtaking rooftop pool that offers stunning views of the skyline. As I ascended to the rooftop, I was greeted by a captivating panorama that made every moment spent poolside feel like a mini-vacation.

For those fortunate enough to stay in the penthouse suite, the spaciousness is simply delightful. It feels less like a hotel room and more like a lavish home away from home. What's remarkable is the blend of urban charm and serene relaxation; however, it is worth noting that the environment can be a bit noisy, especially if you're sensitive to city sounds.

If you’re planning an event, the venue spaces here are perfect for weddings or private parties. The access to the gym is an added bonus for fitness enthusiasts. Overall, The Hotel at Midtown encapsulates a fun, yet professional ambiance that welcomes all kinds of travelers. I left feeling revitalized and inspired—definitely a spot to consider for your next visit to Chicago!

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Holiday Inn & Suites Chicago North Shore (Skokie) by IHG

Highlights
Modern and clean accommodations
Friendly and helpful staff
Complimentary breakfast buffet
Free parking available
Great location in Skokie

During my recent stay at the Holiday Inn & Suites Chicago North Shore (Skokie) by IHG, I was pleasantly surprised by the combination of comfort and convenience it offers. As I stepped into my room, I was greeted by modern and clean accommodations that felt like a cozy retreat from the hustle and bustle of the city. The friendly staff made check-in a breeze, providing helpful recommendations that enhanced my visit.

One of the standout features of this hotel is, without a doubt, the rooftop pool. Swimming under the Chicago skyline was an experience that elevated my spirits! After a refreshing dip, I took advantage of the complimentary breakfast buffet. With a variety of delectable options, I fueled up for a day of exploring.

The location made it easy to access nearby attractions, yet I felt away from the city’s noise. Plus, having free parking was a game-changer! Whether you're visiting for business or leisure, the Holiday Inn & Suites delivers on all fronts, making it an excellent choice for anyone looking for hotels with rooftop pools in Chicago. Don't miss the chance to soak in the skyline views while you unwind!

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Days Inn and Suites by Wyndham Hammond, IN

Highlights
Comfortable beds
Clean and well-maintained rooms
Affordable rates
Convenient location
Nice pool available

When it comes to finding a charming retreat in the hustle and bustle of Chicago, the Days Inn and Suites by Wyndham Hammond definitely leaves a delightful impression. Not only is the pool perched atop the building a sun-soaked sanctuary, but the comfortable beds invite you to relax after a long day of exploring the Windy City.

The rooms are incredibly clean and well-maintained, showcasing a commitment to guest comfort that shines through in every corner. I was pleasantly surprised by the affordable rates, which make this hotel an excellent choice for budget-conscious travelers seeking a taste of luxury.

Convenience is another significant plus; the location allows for easy access to local attractions while offering a quiet retreat to unwind. And let's not forget about that lovely rooftop pool — it’s the perfect spot to sip on a cocktail, soak up the sun, and take in the mesmerizing skyline of Chicago.

In essence, Days Inn and Suites by Wyndham Hammond is a hidden gem that brilliantly combines affordability and charm. If you're looking for a place to dip into relaxation with a rooftop view, this hotel deserves a spot on your radar.

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Ramada by Wyndham Hammond Hotel & Conference Center

Highlights
Great customer service
Clean and nice rooms
Friendly and helpful staff
Inconsistent maintenance
Limited amenities available

Ramada by Wyndham Hammond Hotel & Conference Center offers a delightful stay that's ideal for both leisure and business travelers. Upon arrival, I was immediately impressed by the exemplary customer service—the staff was welcoming, friendly, and eager to assist, making me feel right at home.

The rooms are not only clean but also quite cozy, providing a comfy retreat after a long day of exploring the city. I appreciated the attention to cleanliness; it truly elevates the experience. However, it’s worth mentioning that I encountered some inconsistent maintenance during my stay, which could use a little fine-tuning.

One of the hotel's standout features is undoubtedly the rooftop pool. With a stunning view of the Chicago skyline, it's a refreshing way to unwind. Just imagine soaking up the sun with a cool drink in hand—pure bliss!

While the hotel could benefit from a few more amenities, the friendly and helpful staff, paired with the inviting atmosphere, make this a charming choice for anyone seeking a blend of comfort and relaxation in the Windy City. If you're in Chicago, consider adding this hidden gem to your travel plans!

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Holiday Inn Express & Suites Chicago North Shore - Niles by IHG

Highlights
Friendly and helpful staff
Nice hotel in the area
Satisfying customer experience
Complimentary breakfast options

The Holiday Inn Express & Suites Chicago North Shore - Niles by IHG truly exceeded my expectations. As I stepped into the lobby, I was warmly greeted by the friendly and helpful staff, setting the tone for my stay. The hotel's location is perfectly situated for both relaxation and exploration, capturing the essence of Chicago's charming North Shore.

One of the highlights of my visit was undeniably the rooftop pool. Imagine lounging under the sun with a refreshing drink in hand, soaking in the panoramic views of the city skyline. It's a tranquil escape amid Chicago's hustle and bustle.

The customer experience was notably satisfying, with the staff eager to ensure I had everything I needed for a comfortable stay. Mornings were a delight, thanks to their complimentary breakfast options which provided an excellent start to the day.

Overall, I found myself falling in love with the vibrant atmosphere and modern amenities. If you're seeking a hotel that balances comfort, convenience, and a splash of luxury, the Holiday Inn Express & Suites should be at the top of your list for your Chicago adventure with a rooftop pool. Dive into relaxation and make unforgettable memories!

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Super 8 by Wyndham Morton Grove/Chicago

Highlights
Comfortable and spacious rooms
Exceptional staff hospitality
Friendly and accommodating team
Clean and well-maintained space
Highly recommended by guests

Staying at Super 8 by Wyndham Morton Grove/Chicago was a delightful surprise! Nestled just a short drive from the bustling city, this cozy hotel feels like a home away from home. As soon as I stepped into my room, I was greeted by comfortable and spacious accommodations where I could truly unwind.

But let’s talk about that rooftop pool! This gem offers the perfect spot to soak up the sun while enjoying stunning views of the Chicago skyline. I found it to be a wonderfully relaxing place to sip a cocktail and let the city buzz fade into the background.

The most remarkable part of my stay, however, was the exceptional hospitality. The staff was not only friendly but also incredibly accommodating, ensuring that I had everything I needed for a pleasant visit. With a focus on cleanliness and maintenance, the space felt fresh and inviting.

I highly recommend the Super 8 by Wyndham for anyone looking to enjoy a retreat in Chicago that combines comfort and a splash of fun! Whether you’re here for leisure or work, this place will certainly exceed your expectations. Trust me, it’s worth it!

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Level Chicago - Fulton Market

Highlights
Great location
Amazing views
Beautifully designed suites
Friendly staff
Clean room facilities

Level Chicago - Fulton Market truly captures the essence of urban luxury with its stunning rooftop pool, and let me tell you, it did not disappoint! Nestled in a vibrant neighborhood, the hotel's location is superb, allowing easy access to Chicago's trendiest spots while offering a peaceful oasis to unwind.

As I ascended to the rooftop, I was greeted with breathtaking views of the skyline that made me feel like I was on top of the world. The pool itself is a visual delight, providing the perfect setting for a refreshing dip under the sun.

What really stood out during my stay were the beautifully designed suites. They practically scream sophistication with their modern décor and cozy vibes. It felt like having a home away from home, complete with all the amenities one could possibly need.

I must commend the friendly staff who went above and beyond, providing warm hospitality that made the experience even more enjoyable. Plus, the cleanliness of the room facilities was impeccable, allowing me to fully relax and immerse myself in the luxury of my surroundings.

If you're looking for a thrilling blend of style and comfort in Chicago, Level Chicago - Fulton Market is a must-visit!

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Radisson Blu Aqua Hotel, Chicago

Highlights
Stunning Views
Exceptional Customer Service
Beautiful Rooftop Pool
Spacious, Comfortable Rooms
Scenic Walking Path

Staying at the Radisson Blu Aqua Hotel was an extraordinary delight! As I stepped into this stunning hotel, I was immediately enamored by the beautiful rooftop pool that offered breathtaking views of the Chicago skyline. The ambiance up there was so relaxing that I found myself wanting to soak up the sun all day.

The customer service was exceptional; the friendly staff greeted me with warm smiles and catered to my every need, making my stay even more memorable. My room was spacious and comfortable, providing a perfect retreat after a day of exploring the city. I loved the modern decor that seamlessly blended comfort and style, creating an inviting atmosphere.

One of the hotel’s standout features is the scenic walking path that meanders alongside the pool area, perfect for those picturesque sunset strolls. Whether you're looking to unwind by the pool or venture into the vibrant city, Radisson Blu Aqua caters to all preferences. My experience was not just a stay; it was an experience, and I wholeheartedly recommend it to anyone seeking a slice of paradise in Chicago with the added bonus of a spectacular rooftop retreat. 🌆🏊‍♀️

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Viceroy Chicago

Highlights
Stunning Lake and City Views
Luxurious and Spacious Rooms
Outstanding Attentive Service
Beautiful Art Deco Design
Heated Bathroom Floors

Viceroy Chicago: A Skyline Oasis with a Rooftop Twist

During my recent stay at the Viceroy Chicago, I found myself captivated by the harmonious blend of luxury and sophistication. From the moment I entered, the stunning art deco design enveloped me in a world of elegance. My room was nothing short of a sanctuary with its luxurious and spacious accommodations, making it a perfect retreat after exploring the bustling city.

But let’s talk about the rooftop pool—a true gem! As I lounged by the pool, I was treated to breathtaking views of both Lake Michigan and the twinkling city skyline. The atmosphere up there is vibrant yet serene, making it an ideal spot to unwind with a cocktail in hand. The staff, with their outstanding attentive service, ensured that my experience was nothing short of exceptional.

And for that little touch of indulgence, I found the heated bathroom floors to be a delightful surprise each morning. Viceroy Chicago truly redefines luxury, merging comfort and style effortlessly. If you're seeking a rooftop pool that offers both stunning vistas and lavish amenities, this hotel is a must-visit! Dive into the city’s charm at Viceroy!

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