{"id":829,"date":"2025-09-04T14:07:33","date_gmt":"2025-09-04T19:07:33","guid":{"rendered":"https:\/\/arlohotels.com\/chicago-downtown-hotel\/?p=829"},"modified":"2026-01-29T08:46:20","modified_gmt":"2026-01-29T14:46:20","slug":"september-in-chicago-cant-miss-festivals-fairs-and-events","status":"publish","type":"post","link":"https:\/\/arlohotels.com\/chicago-downtown-hotel\/blog\/september-in-chicago-cant-miss-festivals-fairs-and-events\/","title":{"rendered":"September in Chicago: Can\u2019t-Miss Festivals, Fairs, and Events"},"content":{"rendered":"\n

September in Chicago can be magic. The summer crowds have thinned, the weather is crisp, and the city\u2019s festival season is hitting its stride with some of the year\u2019s best events. From world-class jazz performances to food festivals and art fairs, September in Chicago offers something for everyone. Here\u2019s your complete guide to the can\u2019t-miss festivals, fairs, and events happening around the Windy City this month.<\/p>\n\n\n\n

September Music Festivals <\/h2>\n\n\n\n

Riot Fest<\/h3>\n\n\n\n

September 19\u201321<\/strong>: Riot Fest<\/strong><\/a> is a three-day independent music festival in Chicago specializing in punk, rock, alternative, metal, and hip-hop. This year\u2019s 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.<\/p>\n\n\n\n

Englewood Jazz Festival<\/h3>\n\n\n\n

September 16\u201320<\/strong>: <\/strong>The Englewood Jazz Festival<\/strong><\/a> 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\u2019t find at the larger downtown festivals.<\/p>\n\n\n\n

Hyde Park Jazz Festival<\/h3>\n\n\n\n

September 27\u201328<\/strong>: <\/strong>Closing out the month, the Hyde Park Jazz Festival<\/strong><\/a> offers another neighborhood-focused celebration of jazz. Located in one of Chicago\u2019s 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.<\/p>\n\n\n\n

Cultural & Art Celebrations <\/h2>\n\n\n\n

World Music Festival Chicago<\/h3>\n\n\n\n

September 26\u2013October 5<\/strong>: <\/strong>World Music Festival Chicago<\/strong><\/a> 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.<\/p>\n\n\n\n

Woodstock Art Fair on the Square<\/h3>\n\n\n\n

September 20\u201321<\/strong>: Head to the charming suburb of Woodstock, Illinois, for Woodstock Art Fair on the Square<\/strong><\/a>, a beloved art fair that\u2019s 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\u2019s worth the short trip from the city.<\/p>\n\n\n\n

Food and Drink Festivals<\/h2>\n\n\n\n

Halfway to St. Patrick\u2019s Corned Beef Festival<\/h3>\n\n\n\n

September 20\u201321<\/strong>: A festive celebration of Irish culture and Chicago deli food, the Halfway to St. Patrick’s Corned Beef Festival<\/strong><\/a> is presented by Manny\u2019s Deli<\/a>, an iconic spot serving sandwiches, bagels, and other deli favorites since 1942. You could say it\u2019s kind of like St. Patrick\u2019s 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.<\/p>\n\n\n\n

Long Grove Apple Fest<\/h3>\n\n\n\n

September 26\u201328<\/strong>: The Long Grove Apple Fest<\/strong><\/a> 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.<\/p>\n\n\n\n

Oktoberfest Chicago <\/h3>\n\n\n\n

September 27\u201320<\/strong>: Get your lederhosen ready! West Lakeview\u2019s Oktoberfest Chicago<\/strong><\/a> 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.<\/p>\n\n\n\n

Neighborhood Events and Markets<\/h2>\n\n\n\n

Division Street Farmers Market <\/h3>\n\n\n\n

Fresh seasonal produce, flowers, prepared foods, unique Chicago-made products and rare finds are all available at the Division Street Farmers Market<\/strong><\/a>. While farmers markets happen year-round, September is the peak season for local produce. This is when you\u2019ll 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.<\/p>\n\n\n\n

Chicago Live!<\/h3>\n\n\n\n

September 20\u201321<\/strong>: Navy Pier continues to host live entertainment throughout September, including at Chicago Live!<\/strong><\/a>, the Midwest\u2019s 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\u2019t miss the fireworks finale to close out the weekend.<\/p>\n\n\n\n

September Festival & Event Planning<\/h2>\n\n\n\n

September typically offers ideal conditions for outdoor events in Chicago, as the oppressive summer heat has broken, but you\u2019re 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.<\/p>\n\n\n\n

Many of these events are easily accessible by the \u201cL\u201d, 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.<\/p>\n\n\n\n

As it\u2019s 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\u2019s worth checking individual event websites for the most current information.<\/p>\n\n\n\n

Whether you\u2019re a music lover, foodie, art enthusiast, or just someone who loves a good community get-together, this month delivers experiences you\u2019ll 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\u2019s cultural scene. Happy festing!<\/p>\n","protected":false},"excerpt":{"rendered":"

Looking for fun ways to enjoy the Windy City? 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