AI PlannerChicago in September
Exciting events and experiences happening this month in Chicago.
Chicago Jazz Festival 2025
Celebrating its 47th year, the Chicago Jazz Festival brings together jazz legends and new artists for a series of free concerts in Millennium Park and other venues.
A cornerstone of Chicago's music scene, offering world-class jazz performances for free.
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Taste of Chicago: Fall Edition
Experience Chicago's diverse culinary scene with samples from over 50 local restaurants, food trucks, and pop-ups, alongside live music and cooking demonstrations.
A condensed, autumnal version of the city's iconic food festival, perfect for foodies.
Plan your trip to Taste of Chicago: Fall Edition with our AI-powered travel planner. Get personalized itineraries and recommendations for your visit to Chicago. Book tickets through our platform.
River North Fall Art Walk
Explore the vibrant art galleries of the River North district, featuring new exhibitions, artist talks, and special receptions. Many galleries offer complimentary refreshments.
An excellent opportunity to discover new artists and engage with Chicago's thriving art scene.
Plan your trip to River North Fall Art Walk with our AI-powered travel planner. Get personalized itineraries and recommendations for your visit to Chicago. Book tickets through our platform.
Chicago Half Marathon
Run along Chicago's scenic lakefront, past iconic landmarks, in this popular fall half marathon. Perfect for seasoned runners and those looking for a challenge.
A beautiful course offering stunning city and lake views, culminating in a festive post-race celebration.
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Mexican Independence Day Parade
Join the vibrant celebration of Mexican Independence Day with colorful floats, traditional music, and dance groups marching through the heart of Little Village.
A lively and culturally rich parade showcasing the pride and heritage of Chicago's Mexican community.
Plan your trip to Mexican Independence Day Parade with our AI-powered travel planner. Get personalized itineraries and recommendations for your visit to Chicago. Book tickets through our platform.
Lincoln Park Zoo Fall Fest
Enjoy a family-friendly autumn celebration at Lincoln Park Zoo, featuring a pumpkin patch, corn maze, animal encounters, and seasonal treats. Perfect for all ages.
A cherished annual tradition that transforms the zoo into a festive fall wonderland.
Plan your trip to Lincoln Park Zoo Fall Fest with our AI-powered travel planner. Get personalized itineraries and recommendations for your visit to Chicago. Book tickets through our platform.
Chicago Bears vs. Green Bay Packers (Home Opener)
Witness the fierce rivalry between the Chicago Bears and Green Bay Packers in the highly anticipated home opener of the NFL season at Soldier Field.
One of the most iconic rivalries in American sports, kicking off the NFL season with high energy.
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Chicago Craft Brew Festival
Sample a wide array of beers from local and national craft breweries. Enjoy live music, food trucks, and interactive brewing demonstrations in an outdoor setting.
A fantastic opportunity to discover new brews and connect with the thriving craft beer community.
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Broadway In Chicago: 'The Lion King' Return Engagement
Experience the magic of Disney's 'The Lion King' as it returns to Chicago for a limited engagement. A spectacular visual and musical masterpiece for all ages.
A timeless Broadway classic, renowned for its breathtaking costumes, puppetry, and music.
Plan your trip to Broadway In Chicago: 'The Lion King' Return Engagement with our AI-powered travel planner. Get personalized itineraries and recommendations for your visit to Chicago. Book tickets through our platform.
Chicago Architecture Foundation Center River Cruise: Fall Foliage Edition
Enjoy Chicago's world-renowned architecture from the Chicago River, with a special emphasis on the vibrant fall colors along the riverbanks and city parks.
A perfect blend of stunning architecture, insightful commentary, and the beauty of autumn in the city.
Plan your trip to Chicago Architecture Foundation Center River Cruise: Fall Foliage Edition with our AI-powered travel planner. Get personalized itineraries and recommendations for your visit to Chicago. Book tickets through our platform.
Ready to Experience Chicago?
Plan your perfect itinerary around these amazing events
Use our AI planner to create a personalized Chicago itinerary for September 2025. Chat with our AI assistant to get recommendations for hotels, restaurants, and activities that complement these events. Our intelligent trip planner considers your preferences, budget, and travel dates to create the perfect Chicago travel plan. Features include real-time weather updates, interactive maps, and local insider tips.
