Summer is almost over, but September in Chicago is packed with things to do, including a number of festivals and concerts that will get you into the Fall spirit. Explore Chicago’s best festivals and events – celebrating food, music, culture, art, and history.
Dessert Festival
September 14, 2019 (6:30 to 11 p.m.)
A ticket to Dessert Fest [formerly Donut Fest] includes dessert tastings, interactive games, entertainment, and access to some of the animal areas at Lincoln Park Zoo for all ages. Champagne, beer, and wine will be sold.
Bourbon & BBQ
September 14 – 15 2019
Chicago Bourbon & Barbecue Fest has live music, barbecue kitchens, a bourbon tasting pavilion, and vendor booths filling the streets at Damen Avenue & Roscoe Street. Donation $5.
Oak Park “Oaktoberfest”
September 20 – 21, 2019
Enjoy live music, craft beer, wine, local restaurant food, and a kids’ root beer garden (Sat. noon to 5 p.m.) at Oaktoberfest in Oak Park. Bring cash. Free.
Art Exposition
September 20 – 22, 2019
The International Exposition of Contemporary & Modern Art (Expo Chicago) has museum-quality curated art and design by 135 exhibitors at Navy Pier.
Taco Festival
September 21 – 22, 2019
Try tacos from a dozen restaurants and vote for the best, drink beer, hear live music on two stages, visit the kids’ area, and watch Mexican wrestlers at Lakeview Taco Fest on Southport Avenue (from Addison to Roscoe). Donation $10.
Hyde Park Jazz
September 28 – 29, 2019
Hear jazz performances by 38 top artists indoors and outdoors at the Hyde Park Jazz Festival. Donation.
Chicago Gourmet
September 27 – 29, 2019
Chicago’s iconic Millennium Park will be home to the annual Chicago Gourmet 3 day festival, which kicks off on Friday night with the Hamburger Hop throwdown. Discover new chefs, restaurants, wine, spirits, and more. Visit Chicago Gourmet to start making your plans.
Beer Tasting
September 28, 2019
A ticket to BeerHoptacular gets you 20 tickets to taste 3 ounces from more than 150 craft beers, with live music and food trucks at Vertiport Chicago for age 21+. No pets.
Oktoberfest in Roselle
September 28 – 29, 2019
Oktoberfest at Lynfred Winery includes grape stomping, cork tossing, a lederhosen contest, wine for sale, roasted pork on the menu, and crowds. Free for children age 13 and younger.
Half Marathon & 5K
September 29, 2019
The Chicago Half Marathon begins in Jackson Park and goes along scenic Lake Shore Drive. Free to watch.
One of the best things to do in Chicago this Fall is to take a tour of the Windy City before the cold sets in. Gray Line Chicago offers a number of tours to choose from. Find a reason to go today!
If you need a ride or a designated driver for you and your group, visit Aries Charter Transportation for hourly group charters. We have sedans, SUVs vans, minibuses, motor coaches, and trolleys available.
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