City guides

Fun hotels in Chicago

Discover Chicago's most unique and entertaining accommodations as we journey through the city's top fun hotels.

September 19, 2023
 min read
Last updated:
Jan 15
A view of the Chicago skyline, with the Chicago river in the foreground.

Chicago, the Windy City, is known for its vibrant arts scene, diverse culinary offerings, and iconic architecture. But did you know it's also home to some of the most unique and entertaining hotels around? This article will take you on a journey through the top fun hotels in Chicago, each offering a unique blend of comfort, style, and a dash of the unexpected. Let's dive in, shall we?

The Hoxton Chicago

Nestled in the heart of the bustling Fulton Market District, The Hoxton is a haven for the modern traveler. Its chic, industrial design seamlessly blends with the urban landscape, making it a standout in the city's skyline. The hotel's interiors are a testament to contemporary elegance, with every corner meticulously curated to offer a luxurious experience. The lively social scene at The Hoxton is a major draw, especially the rooftop pool and bar. From here, guests can soak in breathtaking city views, making it an ideal spot for evening relaxation. More than just a hotel, The Hoxton serves as a hub of creativity and community, fostering connections among its guests. 

Moxy Chicago Downtown

From the moment you step into Moxy Chicago Downtown, you're greeted with an energy that's palpable. It feels like entering a party that's in full swing, where every guest is having the time of their life. The hotel's design is vibrant and eclectic, reflecting the dynamic spirit of Chicago. The lobby, which doubles as a bar, is a testament to this, offering a space where guests can mingle, play arcade games, and even enjoy tunes from a vinyl record player. It's not just a place to stay; it's a place to experience. Here, you're encouraged to let your hair down, dance to the rhythm of the city, and fully embrace the vibrant spirit of Chicago. 

The Robey

The Robey is a true embodiment of Chicago's Wicker Park and Bucktown neighborhoods. Situated in a historic Art Deco building, the hotel exudes an old-world charm that's beautifully juxtaposed with modern amenities. Every room tells a story, with vintage furnishings that transport guests to a bygone era. The rooftop lounge is a highlight, offering panoramic city views that are nothing short of mesmerizing. Whether you're sipping on a cocktail or simply gazing at the skyline, The Robey ensures an experience that's both nostalgic and contemporary. After a day of exploring, it's the perfect spot to unwind and reminisce. 

Chicago Athletic Association Hotel

Where history meets entertainment, the Chicago Athletic Association Hotel stands tall. This iconic establishment, which once served as a private men's club, has now opened its doors to everyone. The interiors are a nod to its rich past, with vintage-inspired game rooms that are a delight for both young and old. Guests can indulge in games like bocce, shuffleboard, and billiards, making it a hub of fun and frolic. The rooftop bar is a gem, offering unparalleled views of Millennium Park. Whether you're a history buff or just looking for a good time, this hotel promises an experience that's both enriching and exhilarating.

Freehand Chicago

Freehand Chicago redefines the traditional hotel experience, offering a blend of privacy and community. Situated in the heart of the city, this establishment caters to a diverse range of travelers. With both private rooms and shared accommodations, it's perfect for solo adventurers, groups, and everyone in between. The design is both chic and welcoming, encouraging guests to socialize and share stories. The Broken Shaker, the hotel's award-winning cocktail bar, is a hotspot for both locals and tourists. Serving up innovative concoctions in a laid-back setting, it's the perfect place to unwind and make new friends. At Freehand Chicago, every stay is an opportunity to forge new connections. 

21c Museum Hotel Chicago

A masterpiece in its own right, the 21c Museum Hotel is where art and hospitality converge. This boutique hotel doubles as a contemporary art museum, offering guests a visual feast at every turn. With rotating exhibitions and site-specific installations, art enthusiasts will find themselves immersed in a world of creativity. Each room is thoughtfully designed, reflecting the hotel's commitment to art and culture. Beyond the visual appeal, the hotel offers top-notch amenities to ensure a comfortable stay. Whether you're an art lover or simply seeking a unique experience, the 21c Museum Hotel promises a stay that's anything but ordinary. 

The Gwen, a Luxury Collection Hotel

Strategically located on the Magnificent Mile, The Gwen is a blend of history and modernity. Paying homage to Chicago's rich architectural legacy, the hotel's design is both grand and contemporary. Every detail, from the elegant furnishings to the curated art pieces, speaks of luxury. Guests can indulge in craft cocktails at the hotel's upscale bar or simply relax in their rooms, taking in the stunning skyline views. The Gwen is more than just a hotel; it's a testament to Chicago's timeless elegance. Whether you're in the city for business or leisure, The Gwen ensures a stay that's both stylish and unforgettable. 

Hotel Zachary

Situated directly across from the iconic Wrigley Field, Hotel Zachary is a celebration of Chicago's cultural richness. Drawing inspiration from its historic surroundings, the hotel seamlessly blends classic design with contemporary comforts. The interiors are a nod to the city's architectural heritage, with every room offering a unique experience. The on-site restaurants and bars are a culinary delight, showcasing Chicago's diverse food scene. From local delicacies to international cuisines, there's something for every palate. Not just for baseball enthusiasts, Hotel Zachary is a destination for anyone looking to immerse themselves in the city's vibrant atmosphere.

Kimpton Gray Hotel

The Kimpton Gray Hotel is where sophistication meets whimsy. Located in the heart of Chicago, this establishment offers a refined ambiance, punctuated by playful elements that surprise and delight. The hotel's design is a masterclass in elegance, with subtle touches that evoke a sense of fun. The rooftop bar, with its tropical-themed cocktails, is a favorite among guests, offering a slice of paradise in the urban jungle. For those looking to unwind, the game room, equipped with a pool table and vintage video games, is a nostalgic retreat. At the Kimpton Gray Hotel, guests can indulge in a luxurious experience while embracing their playful side. 

The Drake Hotel

A beacon of grandeur, The Drake Hotel stands as a testament to Chicago's illustrious past. This iconic landmark, with its rich history, transports guests to the Roaring Twenties, an era of opulence and glamor. The hotel's design is a visual treat, with intricate details that hark back to a time of elegance. A highlight is the afternoon tea service, a cherished tradition that offers a taste of the past. But The Drake isn't just about nostalgia; it's also a hub of modern entertainment. The Palm Court comes alive with live jazz performances, and the nightlife scene is vibrant, ensuring that guests have a memorable time.

Chicago is a city that knows how to have a good time, and these hotels embody that spirit. Each offers a unique experience, ensuring your stay in the Windy City is anything but ordinary. So next time you're planning a trip to Chicago, consider one of these fun hotels. You might just find that they become one of the highlights of your visit. After all, who said hotels have to be boring?


*Prices fluctuate based on season and day of the week.

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