Start your holiday shopping early by checking out the masterful work of Mexican artisans at the annual Festival del Arte Popular at the National Museum of Mexican Art on October 13-18, 2026. Witness live demonstrations of intricate Mexican folk art and meet artists from all over Mexico at … [Read more...] about Free Festival del Arte Popular at National Museum of Mexican Art
family friendly
Arts in the Dark Halloween Parade
Head to State Street to celebrate Halloween as the "artist's holiday" with an evening of wonder and creativity at the Arts in the Dark Halloween Parade on October 24, 2026, in the Loop. Recognized as one of the top six Halloween events in the world, the tenth annual Arts in the Dark parade … [Read more...] about Arts in the Dark Halloween Parade
Oktoberfestiversary
Dovetail Brewery and Begyle Brewing serve up their annual fall street festival with Oktoberfestiversary on October 10-11, 2026, in the Ravenswood neighborhood. Enjoy brews, live music and food in the spirit of the season. Sip on special tapings from Beglye and Dovetail while munching on … [Read more...] about Oktoberfestiversary
Jack’s Pumpkin Pop Up
Wander through pumpkin patches and corn mazes while you enjoy the season at Chicago's largest fall festival, Jack's Pumpkin Pop Up, located near Goose Island, from September 19 to November 1, 2026. The large number of all-ages festivities make Jack's one of the most popular fall excursions. … [Read more...] about Jack’s Pumpkin Pop Up
Lincoln Square Ravenswood Apple Fest
Enjoy Fall fun with apple-inspired food, drinks and artisan goods at the beloved Lincoln Square Ravenswood Apple Fest, October 2-4, 2026. Celebrate the new season with a bounty of edible goodness. Midwest farms will be serving up fresh apples and related dishes and local restaurants and … [Read more...] about Lincoln Square Ravenswood Apple Fest
First Lady Fall Cruises
One of Chicago's most iconic experiences is sailing on the scenic Chicago Architecture Center (CAC) River Cruise aboard First Lady and absorbing the city's stunning skyline while learning about its design history. The fun continues through the fall, with cruises floating along the shore … [Read more...] about First Lady Fall Cruises
Destinos Chicago Latino Theater Festival
Celebrate Hispanic Heritage Month along with Latino theater and dramatic creativity at the ninth annual Destinos: Chicago International Latino Theater Festival for three weeks from September 14 to October 11, 2026, at theaters across the city. The Chicago Latino Theater Alliance … [Read more...] about Destinos Chicago Latino Theater Festival
St. Benedict’s Oktoberfest
Get ready for the welcoming traditional German toasts of "Prost!" to echo throughout the courtyard during the 60th annual St. Benedict Oktoberfest on October 2-4, 2026. St. Benedict parish celebrates its German roots with a family-friendly fest that includes German food and … [Read more...] about St. Benedict’s Oktoberfest
Ravenswood ArtWalk
The Ravenswood Corridor community celebrates 24 years of the annual Ravenswood ArtWalk on September 12-13, 2026. The area's artists, manufacturers and brewers will welcome visitors during the ArtWalk with a host of fun and interactive activities. Unfolding from Lawrence to Irving Park St.. … [Read more...] about Ravenswood ArtWalk
Free Printers Row Lit Fest
The Midwest's largest literary festival returns to Chicago's historic Printer's Row neighborhood in the South Loop with the Printer's Row Lit Fest on September 12 and 13, 2026. Stretching out over five blocks, the Printers Row Lit Fest features more than 100 booksellers, interactive … [Read more...] about Free Printers Row Lit Fest
German-American Oktoberfest
Celebrate German heritage in all its forms, including dance, music, and food at the annual German-American Oktoberfest on September 11- 13, 2026, in the Lincoln Square neighborhood. The opening ceremony kicks off at 8 pm on September 11. Commemorating 100 years of German traditions, the … [Read more...] about German-American Oktoberfest
Taste of Polonia
Celebrate Polish culture at the largest Polish festival in the country, Taste of Polonia, scheduled for September 4-7- 2026. The 44th-anniversary festival brings four days of traditional Polish food, music and crafts. The Taste of Polonia festival serves up live music on four stages, art … [Read more...] about Taste of Polonia
