September in Chicago can be magic. The summer crowds have thinned, the weather is crisp, and the city’s festival season is hitting its stride with some of the year’s best events. From world-class jazz performances to food festivals and art fairs, September in Chicago offers something for everyone. Here’s your complete guide to the can’t-miss festivals, fairs, and events happening around the Windy City this month.
September Music Festivals
Riot Fest
September 19–21: Riot Fest is a three-day independent music festival in Chicago specializing in punk, rock, alternative, metal, and hip-hop. This year’s headliners include heavy-hitters like Blink-182, Weezer, Jack White, and Green Day. The event also has carnival rides, food vendors, and sideshow performers to keep the crowds entertained. Held at Douglass Park, Riot Fest is known to be chaotic and loud, but absolutely essential for anyone who loves alternative music.
Englewood Jazz Festival
September 16–20: The Englewood Jazz Festival is part of a special time in Chicago for jazz aficionados, following the Chicago Jazz Festival on Labor Day Weekend. and held the week before the Hyde Park Jazz Festival. This free, community-focused celebration of jazz brings world-class musicians to the South Side, creating an intimate atmosphere that you just won’t find at the larger downtown festivals.
Hyde Park Jazz Festival
September 27–28: Closing out the month, the Hyde Park Jazz Festival offers another neighborhood-focused celebration of jazz. Located in one of Chicago’s most culturally rich areas, this festival combines great music with the charm of the Hyde Park community. This is the 19th edition of the festival, and features dozens of notable jazz musicians and performers.
Cultural & Art Celebrations
World Music Festival Chicago
September 26–October 5: World Music Festival Chicago brings together musicians from around the globe for performances at venues throughout Chicago, including at the Chicago Cultural Center. This citywide celebration offers a great chance to experience everything from traditional folk music to contemporary world fusion, all in one festival.
Woodstock Art Fair on the Square
September 20–21: Head to the charming suburb of Woodstock, Illinois, for Woodstock Art Fair on the Square, a beloved art fair that’s been showcasing fine arts and crafts for decades. You can even channel your own creativity at a live painting class, or let the kids get craft in the Kids Art Zone. With over 100 artists, live music, and great food, this is a weekend event that’s worth the short trip from the city.
Food and Drink Festivals
Halfway to St. Patrick’s Corned Beef Festival
September 20–21: A festive celebration of Irish culture and Chicago deli food, the Halfway to St. Patrick’s Corned Beef Festival is presented by Manny’s Deli, an iconic spot serving sandwiches, bagels, and other deli favorites since 1942. You could say it’s kind of like St. Patrick’s Day without the crowds. This is a just-as-festive, but more relaxed chance to savor all the corned beef, Irish music, and beer as you can handle.
Long Grove Apple Fest
September 26–28: The Long Grove Apple Fest is a charming suburban festival that celebrates the fall harvest, featuring everything apple-related you can imagine. From apple cider donuts to caramel apples, plus live music and craft vendors, this is a perfect family-friendly event that encapsulates the spirit of autumn in the Midwest.
Oktoberfest Chicago
September 27–20: Get your lederhosen ready! West Lakeview’s Oktoberfest Chicago brings authentic German food, beer, and music to the Windy City. Enjoy traditional polka bands, bratwurst, and plenty of beer at this quintessential fall celebration of German culture.
Neighborhood Events and Markets
Division Street Farmers Market
Fresh seasonal produce, flowers, prepared foods, unique Chicago-made products and rare finds are all available at the Division Street Farmers Market. While farmers markets happen year-round, September is the peak season for local produce. This is when you’ll find the best apples, late-season tomatoes, and fall squashes from local farms. The market operates on Saturdays from 7am to noon through October 25, and is located at 30 W. Division Street.
Chicago Live!
September 20–21: Navy Pier continues to host live entertainment throughout September, including at Chicago Live!, the Midwest’s largest free performing arts festival. Attendees can expect to see more than 100 artists, companies, and organizations live on stage (and on boat!). This is the fifth anniversary of the festival, and will feature five world premieres along with other incredible music, dance, and theater performances. Don’t miss the fireworks finale to close out the weekend.
September Festival & Event Planning
September typically offers ideal conditions for outdoor events in Chicago, as the oppressive summer heat has broken, but you’re still getting warm, sunny days perfect for wandering through festival grounds. The crowds are more manageable than during peak summer season, and many events offer a nice combination of indoor and outdoor programming.
Many of these events are easily accessible by the “L”, although for some more far-flung events such as Apple Fest, you may want to drive or take a ride-share to your event. Either way, these events offer a great opportunity to explore Chicago neighborhoods you might not have experienced before.
As it’s such a popular time for events in Chicago, some festivals and fairs like Riot Fest require advance tickets and often sell out. Community festivals like the jazz celebrations are typically free, but it’s worth checking individual event websites for the most current information.
Whether you’re a music lover, foodie, art enthusiast, or just someone who loves a good community get-together, this month delivers experiences you’ll remember long after the sun goes down on all the action. The best part? Many of these events are free or reasonably priced, making September one of the most accessible months of the year to dive deep into Chicago’s cultural scene. Happy festing!
