Dovetail Brewery and Begyle Brewing serve up their annual fall street festival with Oktoberfestiversary on October 11-12, 2025. Enjoy brews, live music and food in the Ravenswood neighborhood. Sip on special tappings from Beglye and Dovetail while munching on sausages, lobster rolls and … [Read more...] about Oktoberfestiversary
fall events
Riverwalk Fall Fest
Experience the beauty of the fall season with the Chicago River as the backdrop at the Island Party Hut Fall Fest on the Chicago Riverwalk on Saturdays, September 20-October 25, 2025. Enjoy autumn festivities like hay rides on the river, pumpkin patches and eating apple cider donuts along the … [Read more...] about Riverwalk Fall Fest
Lincoln Square Ravenswood Apple Fest
Enjoy Fall fun with apple-inspired food, drinks and artisan goods at the Lincoln Square Ravenswood Apple Fest, October 3-5, 2025. 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
St. Benedict’s Oktoberfest
Get ready for the welcoming traditional German toasts of "Prost!" to echo throughout the courtyard during the 59th annual St. Benedict Oktoberfest on October 3-5, 2025. St. Benedict parish celebrates its German roots with a family-friendly fest that includes German food and … [Read more...] about St. Benedict’s Oktoberfest
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 18 to November 2, 2025. 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
Free Time Out Market Fifth Anniversary Party
Join the all-day celebration for five years of food, drinks and events during the Fifth Anniversary Celebration of Time Out Market, on November 16, 2024. Enjoy food and drink specials and live DJs in the West Loop neighborhood. Head to Time Out Market for festivities filled … [Read more...] about Free Time Out Market Fifth Anniversary Party
Andersonville Viking Pub Crawl
The Andersonville neighborhood's historic Swedish roots will be on full display during the sixth annual Viking Pub Crawl down Clark Street on November 17, 2024. Hundreds of revelers will don viking gear and grab a commemorative glass as they visit a dozen bars and restaurants offering specials … [Read more...] about Andersonville Viking Pub Crawl
Chicago Free and Cheap Halloween Events
Whether you like parades, tours, parties or old school trick or treating, there are lots of free and cheap Halloween events to explore all over Chicago. Check out everything from boat rides to shopping and fall fests in our round up below. Chicago Halloween Cruises Float … [Read more...] about Chicago Free and Cheap Halloween Events
Free Chicago Ghost Tour Walk
Listen to creepy stories, walk around spooky downtown landmarks and discover Chicago's eerie past with the free Haunted Chicago Tour with Chicago Walking Tours from October 23- November 2, 2024. Follow the trail of the most haunted spots in Chicago with this guided two-hour … [Read more...] about Free Chicago Ghost Tour Walk
Halloween House Music Party
Halloween just got more spirited with a special Haunted House Music Halloween Party on October 31, 2024. Chicago's homegrown sound will pump through a night of ferocious beats and non-stop dancing. The legendary Farley Jackmaster Funk and Gene Hunt will spin records featuring some of their … [Read more...] about Halloween House Music Party
Ravenswood Costume Crawl
Dive into the joy of the season with a visit to the Ravenswood Costume Crawl, filled with Halloween-themed fun, seasonal goods, treats and drinks on October 30, 2024. This free event will transform Ravenswood's Montrose Avenue of shops and restaurants into a spooky space for sipping, snacking and … [Read more...] about Ravenswood Costume Crawl
Super Horror Rama Film Fest
Dive into the creepiness of the scary season with three nights of obscure horror films at Super-Horror-Rama Film Fest on October 16-23, 2024 in the Lincoln Square neighborhood. Prepare to have petrified fun with a showcase of horror film oddities for two nights straight. The series opens … [Read more...] about Super Horror Rama Film Fest
