Our Favorite Festivals Around Chicago, IL

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Chicago. This vibrant and bustling Midwestern Metropolis is the scene for the arts among literature, film, theatre, comedy, gastronomy, music- all between its renowned skyline and storied neighborhoods. Today, Chicago continues to draw millions of tourists from over the world, and with so much occurring at every part of the year, it’s easy to understand why. Whether a visitor drafting travel plans, returning home to visit friends and family, or a local looking for something to do near home, Chicago has something for everyone. Read on for some of our favorite autumn festivals and events here around the Windy City.

Riot Fest

Riot Fest is one of Chicago’s more exciting attractions, drawing massive crowds to Douglass Park since 2005. On this September weekend, Chicagoans gather outdoors and enjoy music across multiple genres, from rock, punk, hip hop, indie, and with bigger and bigger names each year. Some of these famous faces that have performed at Riot Fest include Run the Jewels, Machine Gun Kelly, Dropkick Murphys, Blink-182, Wu-Tang Clan, Paramore, Queens of the Stone Age, and Tenacious D. Reunions and return performances are also common here, so major fans of particular bands and artists can watch the lineup announcements throughout the year with high hopes. For an electric experience in Chicago’s outdoors, come to Riot Fest. 



The Christkindlmarket is a festive and beautiful attraction of Chicago’s autumntime, an outdoor market and fair celebrating the holidays, and the Chicago area’s strong German-American heritage. At Christkindlmarket, visitors can experience Christmas and the holiday season in a way that reflects Central European tradition, including Christmas trees, live choirs, dance groups, live music, Santa encounters, as well as a wide range of crafts and delicious food such as wines, beers, cookies, kolachkes, strudels, sausages, toys, and handmade souvenirs. The Christkindlmarket is a great opportunity to take photos and enjoy Chicago’s holiday spirit for parties of all sizes and ages.

Arts In The Dark

The Arts In The Dark is a dazzling nighttime display of the city’s arts, including dance teams, costume parades, floats, puppets, live music, and truly unique and innovative displays every year. The Arts in the Dark Parade draws Chicagoans, friends, family, and neighbors alike all along State Street to enjoy this Chicago evening celebrating expression in every form. Ballet teams with a unique routine that accommodates the march’s path, Folclorico dance teams covered in lights and creative two-hand puppets are just some of the fun appearances at the Arts In The Dark festival. For a pleasant experience enjoying the arts and Chicago’s sense of community, come to the Arts In The Dark.

Lincoln Square Ravenswood Apple Fest

Lincoln Square Apple Fest is a family-friendly, (and delicious!) way to appreciate the autumn harvest and get to see a different side of Chicago, where this bustling city unwinds for a weekend to enjoy live music, literature, games, crafts, and the literal fruits of the season. Among apple pies, apple fritters, myriad ciders, and apple dishes of every form come to Lincoln Square Apple Fest, for a slower-paced and wholesome weekend. 


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