Best Hotels with Rooftop Pools in Chicago

Top Hotels in Chicago

This guide to the best luxury, 5-star, and design-forward hotels in Chicago is manually curated by our editorial team based on first-hand research, verified guest reviews, location analysis, and overall service quality. Each hotel is selected to meet high standards of comfort, authenticity, and guest experience.

The Robey, Chicago, a Member of Design Hotels
Hotels
Chicago, IL, USA

Located in the heart of Chicago’s Wicker Park neighborhood, this historic hotel is located 3 miles away from the shopping, dining and entertainment on the Magnificent Mile. On-site dining and free WiFi is available. Hardwood floors and 400-thread count sheets are featured in every light-filled room at The Robey, Chicago, a Member of Design Hotels. A flat-screen TV and a Bluetooth-enabled sound system with TV connectivity is included. Guests can enjoy a morning coffee at Café Robey, which offers New American fare for breakfast, lunch and dinner. You can also grab a drink and a bite after work at The Robey's second floor 90's nostalgia lounge, Clever Coyote. The rooftop lounge, The Up Room, is located on the 13th floor of the hotel and offers year-round city views, lounge seating and an array of cocktails and spirits. Our seasonal rooftop, Solana, is a hidden summertime oasis nestled atop the sixth floor of the Hollander Building. The United Center, home of the Chicago Bulls, is a 14-minute drive away from The Robey, Chicago, a Member of Design Hotels. Lincoln Park Zoo and Wrigley Field are both 3 miles away.

Guest Reviews:

- "Friendly & competent staff." - "It fulfilled our expectations." - "I want to live in the Robey!" - "Great hotel in the heart of Wicker Park" - "The staff was amazing, the facility was amazing, and the free passes to the gym down the street was really a great bonus" - "Great! Highly recommended." - "Comfortable, clean, stylish hotel perfect for local flavor." - "Family wedding in Chicago" - "Amazing staff, updated rooms, great nightlife on site"

The Hoxton, Chicago
Hotels
Chicago, IL, USA

Welcome to The Hoxton, Chicago - your home away from home in the heart of Chicago's West Loop district. While there is so much to do (and eat) in this nook of the Windy City, you may find yourself having a hard time leaving The Hoxton's four walls. We've got 3 bars and restaurants, rooftop pool, room service, a coffee shop, yoga studio, The Apartment - our meeting and events space, and Working From_ - our coworking space (just to name a few). In the lobby, you'll find Cira - a modern Mediterranean restaurant serving breakfast, lunch, dinner and tasty weekend brunch. Up on the roof, there's Cabra - a Peruvian-inspired cevicheria by Chef Stephanie Izard. And finally, for nightcaps and evening sips, head to Lazy Bird where you'll enjoy live music with a cocktail (or two) in hand. As for our rooms, each is air-conditioned with a satellite flat-screen TV, well-appointed interiors, private bathrooms with rain showers and the free Hoxton extras you know to expect from us: tea kettle, coffee and tea, water, mini fridge, blow dryer, Blank toiletries, 24-hour front desk service along with WiFi throughout the hotel. What's more, we're dog-friendly, and offer valet parking for hotel and restaurant guests. We're a short stroll to Willis Tower, Chicago Board of Trade Building and the CIBC Theater. The closest airport is Midway International Airport (MDW) - about 8 miles from The Hox.

Guest Reviews:

- "Gorgeous hotel in a fantastic location, with great amenities and wonderful staff!" - "It was pleaseant. I would return this hotel." - "Had the best stay here. Saw some negative reviews about room size and noise, room size is perfect in my professional opi" - "A great Hoxton super helpful staff" - "Fabulous location with helpful staff" - "We came to attend a wedding and to sightseeing. Chicago left a good impression!!" - "Vibey cool London-esque hotel in a great location."

Chicago Hotels with Parking

Chicago Hotels with Entertainment

best hotels in Chicago
8.5
298 reviews
From $295

Dive into the vibrant nightlife at The Robey, where energy and excitement pulsate through every corner. Enjoy delectable cuisine at Café Robey before heading to the Clever Coyote lounge for retro vibes and craft cocktails. Don’t miss breathtaking city views from the rooftop lounges, The Up Room and Solana, perfect for sipping refreshing drinks as you soak up the lively atmosphere. With Chicago's iconic attractions just a short drive away, your adventure awaits!

best hotels in Chicago
8.3
281 reviews
From $316

Dive into the vibrant nightlife at The Hoxton, Chicago, where the energy never fades. With three dynamic bars and restaurants, including the rooftop gem Cabra, you can indulge in exquisite cuisine while enjoying stunning city views. Unwind at Lazy Bird with live music and cocktails that keep the atmosphere buzzing. Whether you're dancing the night away or mingling over a delicious meal, this is the ultimate destination for those seeking adventure and social connections in the heart of the Windy City.

Chicago Family Friendly Hotels

Chicago Pet Friendly Hotels

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