The summer may fade but the fun in Chicago never does. The city seems to transform with rich autumn colors and crisp air of fall. It’s the perfect time of year to explore Chicago’s unique festivals, each with their own flavor of fun (Be sure to check out the Taste!). Whether you’re a local or a visitor, these fall events are not to be missed. And if you’re planning to attend festivals with a large group, consider booking a charter bus service with Aries Charter Transportation to make your next trip one to remember.
Taste of Chicago
September 6–8, 2024 | Grant Park
Kick off the fall season at the iconic Taste of Chicago in Grant Park. This festival is a food lover’s dream, featuring a diverse range of culinary offerings from some of the city’s top restaurants. It’s a great way to sample all the best food Chicago has to offer all in one place. From deep-dish pizza to international cuisines, there’s something for every kind of palate. The Taste also includes live music and family-friendly activities, making it a must-see event for everyone. Similar food events around Chicago include the Taste of Polina, Taste of Arlington Heights, Taste of Evanston, and Taste of Glenview.
German-American Fest
September 6-8, 2024 | Lincoln Square
For a taste of Germany in the heart of Chicago, head to the German-American Fest in Lincoln Square. This lively fall festival celebrates German heritage with traditional music, dancing, and, of course, plenty of beer. It’s an excellent chance to experience Chicago’s cultural diversity and enjoy some authentic German food while you’re there.
Printers Row Lit Fest
September 7-8, 2024 | Printers Row
Book lovers, rejoice! The Printers Row Lit Fest is back with a weekend full of author readings, panel discussions, and book signings. It’s the largest free outdoor literary event in the Midwest, attracting writers and readers from all over. The lit fest is a great way to discover new authors while indulging in your love for literature.
Jack’s Pumpkin Pop-Up
September 21 – November 5, 2024 | Goose Island
Jack’s Pumpkin Pop-Up is one of the biggest fall experiences in Chicago. Located on Goose Island, this autumn pop-up features a corn maze, pumpkin patch, axe throwing, and so much more. It’s really an Instagram-worthy event that’s perfect for all ages. Whether you’re planning a family outing or a fun day with friends, a charter bus will make sure that everyone arrives together and on time, ready to enjoy the autumn festivities.
Oktoberfest Chicago
September 27-29, 2024 | St. Alphonsus Church
Oktoberfest Chicago at St. Alphonsus Church is a much beloved tradition in the city, offering a weekend filled with German beer, brats, and live music. The event captures the spirit of Bavarian culture and is the perfect way to welcome in the fall. If you’re planning to attend with a large group, a charter bus from Aries Charter can simplify your transportation needs, allowing you to focus on enjoying the festivities. It’s the perfect way to see Oktoberfests throughout the Chicago area.
Hyde Park Jazz Festival
September 28-29, 2024 | Hyde Park
Jazz enthusiasts won’t want to miss the Hyde Park Jazz Festival. This annual fall event features performances from some of the best local and international jazz musicians. Set in the historic Hyde Park neighborhood, it’s a two-day celebration of music and culture.
Lincoln Square Ravenswood Apple Fest
October 5-6, 2024 | Lincoln Square
How do you like these apples?! End your fall festival tour with the Lincoln Square Ravenswood Apple Fest. This family-friendly event celebrates what we love about apples, with vendors offering everything from apple pie to cider. There are also plenty of activities for the kids, making it a perfect outing for families.
Chicago’s fall festivals offer something for everyone, from foodies and bookworms to music lovers and cultural enthusiasts. With Aries Charter Transportation, you can enjoy these September events in Chicago with the convenience of group transportation, ensuring that your only focus is having a great time. Book your charter bus today and experience the best of Chicago’s fall festivals with ease.