With a calendar packed with once in a century celebrations and global events, Chicago is set to be one of the most exciting destinations to visit in 2026. Whether travellers are looking to tick off an iconic road trip, immerse themselves in world class music and culture, experience major sporting moments, or explore America’s history at a pivotal time, Chicago has the answer.
From the centenary of Route 66 to UNESCO’s 15th International Jazz Day, 2026 offers a rare opportunity to experience Chicago at a truly landmark moment.
Chicago’s Next Culinary Chapter
Known for its incredible culinary scene, Chicago will be adding to its vast portfolio of eats in 2026. Osaka, the globally celebrated Peruvian Japanese fusion restaurant, will be opening its doors in the Fulton Market District in early 2026, offering a menu built around ceviche, tiraditos, nigiri and signature dishes. Recently opened, The Alston is a brand new steakhouse destination in Chicago’s Gold Coast neighbourhood that draws inspiration from French nouvella cuisine to offer a refined yet lavish dining experience. For a taste of the Mediterranean, travellers can visit Kouklas Greek Eatery, a contemporary ingredient driven dining destination created by the James Beard Award-winning chef Jimmy Bannos Jr. and Kevin Stack. Inspired by Bannos’ childhood, this restaurant brings the flavours and rituals of Greek cuisine to the North Shore. For those looking to enjoy a cocktail in the city, Bar Bambi, which is opening soon, will offer an imaginative cocktail lounge that blends classic structure with modern techniques, making it the perfect place to end the night.
A Global Capital of Jazz in 2026
In 2026, Chicago will take centre stage in the global jazz world as the official host city for UNESCO’s International Jazz Day, the world’s largest international celebration of jazz. Taking place on 30th April 2026, the 15th annual International Jazz Day celebrations will transform the city into a vibrant, citywide festival of sound, bringing together legendary artists, rising talent and music lovers from around the world. To further enjoy Chicago’s jazz connection, travellers can take a trip to The Art Institute of Chicago and explore the brand new Matisse’s Jazz: Rhythms in Color exhibit which showcases the complete set of prints from Henri Matisse’s groundbreaking jazz project. International Jazz Day 2026, kicks off a year of cultural milestones including the 250th anniversary of the United States, the 100th birthday of jazz legend Miles Davis and the highly anticipated opening of the Obama Presidential Center in June on Chicago’s South Side, the epicentre for Chicago style jazz in the early 1900s.
Return of the Road Trip – Route 66 Centenary
With the legendary Route 66 celebrating its 100th anniversary in 2026, there’s no better time to visit Chicago and follow an itinerary that brings the history of the Mother Road to life. Travellers can begin at the official Route 66 start sign in Downtown before heading to Skydeck Chicago at Willis Tower for panoramic views that put the city, and route, into perspective.
From there, travellers can stroll along the historic Michigan Avenue or explore the Chicago History Museumin Lincoln Park, where exhibits on the city’s transport heritage help contextualise the era in which Route 66 was born. Travellers can also enjoy a classic road trip diner experience with a stop at iconic diner Lou Mitchell’s, a long-standing favourite serving classic breakfasts and lunches to Route 66 travellers for almost a century.
Multigenerational Hotspot
2026 travel trend reports continue to point to strong growth in multi generational travel, with families seeking destinations that offer meaningful shared experiences alongside flexibility for different ages and interests. Chicago excels on both fronts, making it easy for grandparents, parents and children to enjoy the city together. Families can explore world class attractions like the Field Museum, meet Sue the T. rex, or enjoy panoramic views of the city at 360 CHICAGO.
For shared entertainment, Broadway In Chicago brings major productions to iconic venues, while the Chicago Architecture cruise offers a relaxing way for all generations to take in the skyline while learning all about the history behind Chicago’s majestic buildings.
After a full day of exploring, families can unwind at the renowned The St. Regis Chicago with its Family Traditions Package, which blends comfort, creativity and personalised service, from monogrammed robes to thoughtful handcrafted amenities. The package also includes a curated itinerary featuring nearby highlights such as Millennium Park and the Shedd Aquarium, making it easy for families to maximise their time in the city.
Sports in the City
With sports travel evolving and fans seeking more authentic local game-day experiences, Chicago stands out as a must visit city for sports lovers in 2026. Home to iconic teams including the Chicago Bulls, Chicago Blackhawks, Chicago Cubs and Chicago Bears, the city offers year round opportunities for visitors to immerse themselves in true American sports culture, from historic arenas to neighbourhood sports bars packed with local fans.
Chicago’s sporting calendar continues to grow with the return of the Chicagoland Speedway, reopening after a six-year hiatus to host a brand-new NASCAR Cup Series Points between 3rd-5th July. Rounding out the year, the iconic Bank of America Chicago Marathon will also return for its 48th edition on 11th October 2026 to guide runners through 29 of the city’s vibrant neighbourhoods. This year, Athletes Unlimited Softball League has formally announced the return of the Chicago Bandits as Chicago’s newest women’s professional sports team, bringing a women’s professional softball team back to the city where the sport was born.
With a growing appetite for live sport among international travellers, Chicago delivers unforgettable, citywide game-day energy making it the perfect destination to experience American sport beyond the stadium lights.
For more information on Chicago, please visit choosechicago.com
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