Things to do in Chicago in September

September is one of my favorite months in Chicago. The stifling summer humidity fades, but the crippling winter cold is still a few months away. Days are warm and sunny and nights slowly get chillier. Shop windows fill with the clothes of the coming season, colorful tights worn with tall boots, jackets and scarves, and thoughts turn to pumpkin patches and apple picking. If you're planning a September visit, here's what to do while you're here.

The weather helps. By the National Weather Service's 1991-2020 normals, September averages a high of 75.5°F and a low of 57.1°F at O'Hare, with about 3.2 inches of rain, and the summer crowds thin out once school starts. See our Chicago weather page and what to wear in fall. Festival dates move every year, so for exact dates check the city's festival dates page or each event's own site.

Chicago Jazz Festival (Labor Day weekend)

The Chicago Jazz Festival is free and runs over several days leading into Labor Day, with sets at the Chicago Cultural Center and the headliners on the Pritzker Pavilion stage in Millennium Park. The city programs it with the Jazz Institute of Chicago, and the lineup mixes Chicago players with national and international names. There are pre-festival shows in the week before, too. You can't bring your own alcohol into Millennium Park for this one, but it's sold inside. Our Labor Day weekend page has more, and blues and jazz clubs will keep you going after the last set.

Mexican Independence Day (early to mid-September)

Mexico's Independence Day is September 16, and Chicago celebrates it for weeks. Pilsen goes first, with a parade that steps off at 18th Street and Newberry Avenue and ends in Harrison Park, with free music afterward. In 2026 it was on the first Saturday of the month.

The big one is the 26th Street Mexican Independence Day Parade in Little Village, run by the Little Village Chamber of Commerce for more than 50 years. It starts at the Little Village Arch at 26th Street and Albany Avenue and heads west about two and a half miles to Kostner Avenue, with floats, mariachis, folkloric dancers and charros on horseback. The city says it draws more than 400,000 people, which makes it one of the largest parades in the Midwest. Come early and eat your way along 26th Street afterward.

Downtown, El Grito Chicago is a ticketed weekend festival in Grant Park with regional Mexican music, a market of local vendors and food from Chicago's Mexican restaurants.

Oktoberfest in Lincoln Square (mid-September)

Yes, it's in September, same as Munich. The German-American Oktoberfest sets up at Western and Leland avenues in Lincoln Square, the old German neighborhood, and a parade heads up Lincoln Avenue from Irving Park Road on the Saturday. Take the Brown Line to Western, then find a seat in the beer tent.

Street fests and craft fairs

The street festival season isn't over yet. Retro on Roscoe takes over Roscoe Street between Damen and Leavitt for three days with oldies bands, a classic car show and food from Roscoe Village restaurants. It's the only fundraiser for Roscoe Village Neighbors, so pay the suggested donation. The Renegade Craft Fair, which started in Wicker Park in 2003, holds its September fair on Division Street, with handmade goods from small makers. It's a good place to shop for gifts that didn't come from the Magnificent Mile.

Riot Fest (mid to late September)

Riot Fest is three days of punk, rock, hip-hop and metal in Douglass Park on the West Side, and it's been going since 2005. It's known for reunions and full-album sets. The main entrance is at Ogden Avenue and Sacramento Drive. The Pink Line is the easiest way in. The festival pushes transit, bikes and rideshare, though it now sells off-site parking too. It's ticketed.

Chicago Gourmet (late September)

Chicago Gourmet is the Illinois Restaurant Association's food and wine festival, with events over several days on the Harris Theater Rooftop in Millennium Park. More than 100 chefs take part, including Chicago names like Stephanie Izard and Rick Bayless, and the program includes a burger competition, a tacos and tequila party and Grand Cru, the big wine tasting. Each event is ticketed separately. Proceeds go to the association's educational foundation.

World Music Festival Chicago (late September into October)

The city's World Music Festival is still going, and it's free. It runs for about ten days at venues across the city, with musicians from Chicago and around the world. The highlight is Ragamala, an all-night concert of Indian classical music in Preston Bradley Hall at the Chicago Cultural Center, which the city calls the largest all-night presentation in the country. The ragas are played through the night and into the morning, the hours tradition sets for them.

Outdoors while it lasts

Lifeguards leave the beaches after Labor Day, and the Park District prohibits swimming outside the season, but the sand and the Lakefront Trail are at their best now, warm and less crowded. The city's farmers markets run through October, and September brings the first apples. It's the best month of the year for an architecture cruise or a walking tour (see sightseeing tours), a patio dinner (outdoor dining spots), or a late-season game at Wrigley Field.

On a rainy day, head for the museums. Our free museum days page tracks which ones are free and when, and the National Museum of Mexican Art in Pilsen is free every day it's open, which makes it a natural stop during Independence Day season.

One thing people get wrong. Open House Chicago, the Chicago Architecture Center's free weekend of access to more than 200 buildings, is in October, not September. See Chicago in October and things to do in Chicago in October.

>> things to do in Chicago in fall
>> things to do in Chicago in August
>> holidays and events in Chicago

Photos by afloden, Plaubul Makina