Chicago is an incredible city, but if you’ve never been here, it can feel very overwhelming. Whether you are organizing a high-energy team outing, an elegant evening for clients, or just need inspiration for your next hosted experience, Chicago’s dynamic mix of art, architecture, cuisine, and culture will guarantee an incredible experience. If you’re new to the city, there are some must-do’s, so we’ve narrowed it down to five standout activities that capture the heart of the city and offer memorable experiences you can recommend to your group, or incorporate into your plans.
1. Spend an Afternoon at the Art Institute of Chicago
Ranked one of the best museums in the world by TripAdvisor, The Art Institute of Chicago is the second largest art museum in the US with almost one million square feet of exhibition space and a permanent collection of 300,000 works. A crown jewel of the city’s cultural landscape, the Art Institute of Chicago is more than just a museum—it’s an experience. Home to one of the most impressive collections in the world, it features iconic works like American Gothic, Nighthawks, and A Sunday on La Grande Jatte, as well as rotating exhibitions that span centuries and continents. The Modern Wing, designed by Renzo Piano, offers stunning architectural views of Millennium Park and serves as an inspiring venue for elevated client events. Whether you’re hosting a small group or simply exploring on your own, the Art Institute delivers beauty, reflection, and a world-class dose of culture every time.
2. Step Out on the Skydeck at Willis Tower
You can’t visit Chicago without looking out over it—and there’s no better way to see it than from the Skydeck at Willis Tower. Located on the 103rd floor of one of the tallest buildings in the Western Hemisphere, this observation deck offers breathtaking views spanning up to four states on a clear day. The main attraction? The Ledge—a series of glass boxes that extend outside the building, allowing brave visitors to stand 1,353 feet above the city. It’s a thrill for first-timers and a must-snap photo op. For groups, the Skydeck also offers VIP experiences and event space with stunning sunset backdrops and skyline brilliance.
3. Dine Around the Fulton Market District
We’ve long loved Fulton Market for its evolving culinary scene, but 2025 might be its best year yet. Once a gritty meatpacking district, this area now rivals the country’s top food neighborhoods. If you can get it, cocktails at The Aviary are unbeatable. Meanwhile Aba, boasts not only some of the best Mediterranean food, but it is also one of the most beautiful restaurants in the city. With new openings from Michelin-starred chefs arriving quarterly, there’s always something fresh to try. For planners, the district offers a range of group dining options and private dining rooms perfect for tastings, team dinners, or celebratory outings.
4. Explore the Chicago Architecture Center River Cruise
Locals will tell you the The Chicago Architecture Center’s River Cruise is one of the best activities you can enjoy in the city. Voted one of the top boat tours in the country, it is led by trained volunteer docents who make 130 years of architectural history feel fresh and thrilling. The Chicago River The open-air deck, skyline views, and bar service create a memorable, educational journey through the city’s steel-and-glass spine. Ideal for hosting out-of-town guests or adding an experiential twist to a client appreciation event.
5. Attend a Seasonal Event at Navy Pier’s Offshore Rooftop
Yes, Navy Pier is touristy—but don’t sleep on Offshore, certified by Guinness World Record as the nation’s largest rooftop venue, located at the far east end of the pier. The views are unbeatable, and the space has matured into one of Chicago’s premier indoor/outdoor event destinations. Whether you’re catching fireworks on a summer Wednesday, hosting a winter cocktail hour in a glass-walled lounge, or attending one of Offshore’s curated pop-up experiences (past themes include après-ski, rosé all day, and international street food nights), it’s a venue that offers a polished yet approachable vibe. Plus, the pier’s recent revitalization efforts have improved walkability and access, making it more planner-friendly than ever.
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