Chicago is the city that’s never done and never outdone — especially when it comes to winning awards.
Hot off the heels of being voted Best Big City in the U.S. for a historic ninth year in a row, Chicago was just named one of the Best Places to Go in 2026 by Frommer’s.
This prestigious list of global destinations is compiled each year by an award-winning roster of travel experts.
What makes Chicago a top destination to visit in 2026? It’s shaping up to be a milestone year for the city, with exciting new openings, massive citywide celebrations, historic anniversaries, and so much more happening all year long.
Check out some of the most exciting events and updates coming to Chicago in 2026 and start planning your visit today:
Obama Presidential Center
Chicago’s long-awaited Obama Presidential Center is officially slated to open in 2026.
This lively community hub, located in the heart of the historic Hyde Park neighborhood, will feature a museum, auditorium, library branch, athletic facility, garden, and more across its 19-acre lakefront campus. Visitors can enjoy a dynamic array of community events, exhibits, performances, workshops, talks, and more.
The Hand & The Eye
Attention magic fans – The Hand & The Eye will become the world’s largest magic venue when it opens in Chicago next year.
Set to debut in spring 2026, the immersive venue will be taking over the McCormick Mansion just off The Magnificent Mile. Guests will be invited to explore and interact as they journey through 37 unique rooms across multiple floors. Art and artifacts throughout the space will pay homage to the influence and history of magic in Chicago.
International Jazz Day
Chicago has been selected as the official host city for UNESCO’s International Jazz Day 2026, the world’s largest celebration of jazz.
This event will be held on April 30, 2026, spotlighting the city’s vast contributions to jazz, blues, and global music culture. As the birthplace of Chicago-style jazz, our city has long attracted innovative musicians such as Herbie Hancock, Louis Armstrong, and Nat King Cole. Throughout the year, you can catch diverse performances in the city’s many historic jazz clubs.
Route 66 centennial
Celebrate the 100th anniversary of America’s most iconic road trip with a trip to Chicago, the official starting point of the route.
The centennial of Route 66 in 2026 will bring milestone celebrations to the city throughout the year. Known as “The Mother Road,” this legendary highway begins in downtown Chicago and runs more than 2,400 miles to the Pacific Coast. Highlights along the Chicago stretch of the route include historic landmarks, retro diners, and more.
Check out more hot Chicago happenings in 2026
- Chicago Restaurant Week (Jan. 23 – Feb. 8, 2026)
- Chicago Theatre Week (Feb. 5 – 15, 2026)
- Yoko Ono: Music of the Mind (through Feb. 22, 2026)
- Illinois 250 (year-round)
- James Beard Awards (June 15, 2026)
- Theater of the Mind from David Byrne (March 11 – May 31, 2026)
- NCAA March Madness Midwest Regional (March 27 – 29, 2026)
- The 2026 Presidents Cup at Medinah Country Club (Sept. 22 – 27, 2026)
- Bally’s Chicago Casino (opening in 2026)
More recent awards for Chicago
- Time Out Magazine named Chicago one of the Best Cities for Culture in the world—the only U.S. city to make the list.
- Chicago’s Avondale neighborhood was also named the world’s fifth coolest neighborhood by Time Out and the top-ranked neighborhood in the U.S.
- Chicago has been ranked the safest city for LGBTQ+ travelers, according to the 2025 Misterb&b’s Queer Safety Index.
- Travel Noire named Chicago the Best Stateside Vacation in its 2025 Travel Noire Awards.
- Condé Nast Traveler‘s prestigious Readers’ Choice Awards ranked Chicago first on their list of Best Big Cities in the U.S. for an unprecedented ninth consecutive year.
