Weekend 101: 7 Things to Do Around Chicago Sept. 27-29

Love food? Then you’ll love this weekend. Sample fare from celebrity chefs at Millennium Park, dine on dumplings at Navy Pier, celebrate Oktoberfest with local craft beer and hard cider, and more.

Chicago Gourmet

Sept. 24-29

Chicago Gourmet
Photo by Neil John Burger.

Watch cooking demonstrations by chefs like Rick Bayless, Stephanie Izard, Carrie Nahabedian, and Fabio Viviani; enjoy special encore events like Battle of the Masters at Swift & Sons, Hamburger Hop, and The Big Chill(i): Gourmet Chili Cook-Off on the Harris Theater Rooftop; and sample delicious fare throughout Millennium Park during this annual foodie fest.


Sept. 28

BeerHoptacular in Chicago
Photo by Elevate on Unsplash.

The city’s “original craft beer festival” takes place in a helicopter hanger, so not only can you sample from more than 100 brews and dine on offerings from local food trucks, but you can also take a helicopter ride.

Harvest Weekend

Sept. 28-29

Harvest Weekend at Chicago Botanic Garden
Photo courtesy of Chicago Botanic Garden.

Fall might just be the best time to spend a weekend at Chicago Botanic Garden, especially during events like this. Leave with tips for your home garden, a new cookbook from the cookbook swap, treats from vendors like Joe’s Blueberries and Tiny But Mighty Popcorn, and more.

Evanston Oktoberfest

Sept. 29

Evanston Oktoberfest
Photo courtesy of Downtown Evanston.

Celebrate the season with live music from German band Die Musikmeisters and local band Railheart, German dancers, a stein-holding contest, arts and crafts, and craft beer, hard cider, and food from area breweries and restaurants. Plus, you can enjoy even more traditional Oktoberfest fun with Chicago’s event Sept. 27-29.

World Dumpling Fest

Sept. 29

World Dumpling Fest in Chicago
Photo by Charles 🇵🇭 on Unsplash.

Head out to Navy Pier for this celebration of cultures around the world with performances, food, and activities.

More Can’t-Miss Events:

  • Don’t miss Fall Fest in Winnetka on Sept. 28 for Touch-A-Truck, inflatables, face painting, a pumpkin roll, food and drinks, and more.

Make a Difference:

  • Discover a new beer while making a difference during the Chicago Fire Foundation’s Fire-tober Fest Sept. 28. All proceeds from this day of beer, food, and music will benefit the foundation’s P.L.A.Y.S. (Participate, Learn, Achieve, Youth, Soccer) Program.

Anna Carlson writes the weekly Weekend 101 column and monthly Recommended Events. A graduate of the University of Missouri, her work has been published in Chicago Parent, Inside Columbia Magazine, and Central California Parent Magazine. She is a proud supporter of St. Jude Children’s Research Hospital