1. Fire-tober Fest: Who says fall can’t be red hot? Kick off the season with the Chicago Fire Soccer Club while sipping on over 30 craft beers from numerous local and national breweries. Guests can sample drinks, snack on tasty buffet bites and participate in raffles throughout the night, with all proceeds going to the Chicago Fire Foundation. Sept. 23, 12PM, tickets from $40, 940 W. Weed St.
2. Fall Dinner Crawl: Calling all foodies for this flavor-packed event. This annual dinner crawl takes revelers on a tasty adventure around the Wicker Park and Bucktown neighborhoods. With three separate routes to choose from, guests can decide where they want to enjoy scrumptious fall themed foods like Pecan pie bites and sweet potato tacos. Featured restaurants include Fonda Frontera, Antique Taco and Urbanbelly. Sept. 26, 6-9PM, tickets from $45
3. Revolution Oktoberfest: Revolution Brewing will take their sixth annual Oktoberfest event to the streets this year—Milwaukee Ave. specifically. Partnering with the Chicago Distilling Company, Dönerman and the Radler, guests can taste their popular Revolution drafts and rock out to live music headliners Real Estate and Jeff Rosenstock. After the fest, guests can also check out various after parties along the Milwaukee Ave. corridor. Sept. 29-30, 5 PM, $5 donation, Milwaukee Ave between California Ave and Fullerton Ave.
4. Oktoberfest Chicago: This Chicago take on the classic German festival returns to St. Aplhonsus Church for patrons to enjoy the traditions, brews and foods of our German friends. The community celebrates this gathering with Handmade bratwursts, 40 craft beer options and authentic German live music to help guests get a peek into this popular German holiday. All are welcome. Sept. 29-Oct.1, 6PM, tickets $40, 1429 W. Wellington Ave., St. Alphonsus Church
5. Beer in the Woods: Step away from the hustle and bustle of city life and enjoy a few brews in the woods at this North Side fest. Hosted by Friends of Forest Preserves, guests can sip on beer and ciders from over 30 breweries in an impressive beer tent. Those who attend also have the opportunity to purchase custom engraved beer mugs, listen to live music and watch home brewing demonstrations. Sept. 30, 1PM, VIP tickets $65, LaBagh Woods