Family Friendly

Free Time Out Market Oktoberfest

Join a three-day Oktoberfest celebration at the Timeout Oktoberfest, on October 7-9, 2022. Enjoy German beer, music and a pop-up bar in the West Loop neighborhood. Head to Time Out Market for Oktoberfest festivities filled with stein hoisting contests, German band performances a DJ and … [Read more...] about Free Time Out Market Oktoberfest

Oktoberfestiversary

Dovetail Brewery and Begyle Brewing serve up their annual fall street festival with Oktoberfestiversary on October 8-9, 2022. Enjoy brews, live music and food in the Ravenswood neighborhood. Sip on special tappings from Beglye and Dovetail while muching on sausages, lobster rolls and … [Read more...] about Oktoberfestiversary

St. Benedict’s Oktoberfest

Get ready for the welcoming traditional German toasts of "Prost!" to echo throughout the courtyard during the 56th annual St. Benedict Oktoberfest on September 30-October 2, 2022. St. Benedict parish celebrates its German roots with a family-friendly fest that includes German food and … [Read more...] about St. Benedict’s Oktoberfest

Lincoln Square Ravenswood Apple Fest

Enjoy Fall fun with apple-inspired food, drinks and artisan goods at the Lincoln Square Ravenswood Apple Fest, October 1-2, 2022. 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 food … [Read more...] about Lincoln Square Ravenswood Apple Fest

Chalk Howard Street

The fun and creativity of chalk art will transform Rogers Park's Howard Street during the annual Chalk Howard Street on August 27, 2022. This free event hosts internationally renowned 2D and 3D artists from around the country. Chalk Street Howard is Chicago's only chalk fest and … [Read more...] about Chalk Howard Street

Taste of Polonia

Celebrate Polish culture at the largest Polish festival in the country, Taste of Polonia, schedulded for September 2-5, 2022. The 40th 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

Taste of Italy at World Market

The new Italian shop at World Market Lincoln Park introduces authentic Italian flavors and products to Chicago with a free Taste of Italy event on August 18, 2022. Savor the richness of gourmet Italian brands representing each of Italy's 20 regions during the Taste of Italy event which runs all … [Read more...] about Taste of Italy at World Market

Bud Billiken Parade

Head to the Bronzeville neighborhood to witness the second largest parade in the U.S. after the Rose Bowl; the historic Bud Billiken Parade celebrates 93 years of African American music, pageantry and community on August 13, 2022. Filled with over 200 elaborate marching bands, drill teams, … [Read more...] about Bud Billiken Parade

Noche Caribena at Navy Pier

Celebrate the spirit of Puerto Rican culture during Noche Caribena, (Caribbean night) an evening of free Puerto Rican music and dance at Navy Pier's Polk Brothers stage, on August 13, 2022. Hosted by the Puerto Rican Arts Alliance , Noche Caribena features an array of traditional and … [Read more...] about Noche Caribena at Navy Pier

Meet Me on The Mile Free Events

The splendor of Michigan Avenue will be in full effect during the return of the Meet Me on The Mile events from August 18, 2022, to October 1, 2022. A full calendar of free cultural, culinary and health-focused happenings will bring even more activity to the Gold Coast … [Read more...] about Meet Me on The Mile Free Events

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 10 and 11, 2022. Stretching out over five blocks, the Printers Row Lit Fest features more than 100 booksellers, … [Read more...] about Free Printers Row Lit Fest

Chicago Air & Water Show

With planes swirling in the sky and boats racing through the water, the Chicago Air & Water Show is the most spectacular event of the Summer. Scheduled for August 20 and 21, 2022, this year's show celebrates over 60s years of dazzling stunts over the iconic Chicago skyline. The largest and … [Read more...] about Chicago Air & Water Show