Fall is in full swing in Chicago, and this weekend is packed with events you won’t want to miss! From celebrating Bavarian traditions at Oktoberfestiversary to catching a movie under the stars with Rooftop Cinema Club, enjoying seasonal fun at Fall Fest on the Riverwalk, or cheering on runners at the Bank of America Chicago Marathon, there’s something for everyone. Here’s a look at what’s happening around the city this weekend.
🍺 Oktoberfestiversary 2025
📍 Location: Between Begyle Brewing & Dovetail Brewery, 1800 W Cuyler Ave, Chicago, IL 60613
📅 Dates: Saturday & Sunday, October 11–12, 2025
⏰ Event Hours: 11:00 AM – 9:00 PM
💰 Admission: Free; $5 suggested donation at the gate
🎟️ Tickets: Event Details
More info
Oktoberfestiversary returns for its 10th annual celebration, hosted by Begyle Brewing and Dovetail Brewery in the Ravenswood Corridor. This family-friendly event offers a variety of activities for all ages, including live music performances, food trucks, and special beer tappings. The event also supports The Friendship Center, a local food pantry, with a portion of proceeds benefiting their mission to provide meals to those in need.
🎬 Rooftop Cinema Club – Fulton Market
📅 Date: Friday, October 10 – Sunday, October 12, 2025
📍 Location: The Emily Hotel Rooftop, 311 N Morgan St, Chicago
🕘 Times: Multiple showings daily (starting as early as 11:00 AM)
Enjoy a weekend of Halloween-themed movies under the stars at this open-air rooftop cinema. Friday features Hocus Pocus, Scream, and Scream 2. On Saturday, there’s a Hocus Pocus character meet-and-greet at 11:00 AM, followed by The Nightmare Before Christmas. Sunday brings a themed Wicked screening with mimosas and muffins at noon, and Beetlejuice closes out the weekend at 6:30 PM. With wireless headphones, cozy seating, skyline views, and seasonal snacks, it’s a must for fall movie lovers. Daytime shows are family-friendly; evening shows are typically 16+.
🎟️ View full schedule and ticket info here: rooftopcinemaclub.com/chicago
🍂 Fall Fest on the Riverwalk
📅 Date: Every Saturday — September 20 to October 25, 2025
📍 Location: Island Party Hut, 355 Chicago Riverwalk, Chicago
🕘 Time: 12:00 PM – 8:00 PM (live music 1:00‑4:00 PM & 5:00‑8:00 PM)
This seasonal event transforms the Chicago Riverwalk into a festive fall celebration with hayrides on the river, a pumpkin patch, photo ops, jumbo games, and fall treats like apple cider donuts and themed cocktails. The fest is family-friendly during the day, with games, snacks, and activities that kids can enjoy, plus welcome drinks for all ages. While there are adult-oriented elements like beer and cocktails later in the day, the early afternoon hours are best for families with young kids. Tickets start around $5 and include music, games, and a welcome beverage.
🏃♀️ Bank of America Chicago Marathon
📅 Date: Sunday, October 12, 2025
📍 Location: Grant Park and various neighborhoods across Chicago
🕘 Start Time: Waves begin at 7:20 AM
Cheer on thousands of runners as they make their way through Chicago’s 26.2-mile marathon course, winding through 29 unique neighborhoods filled with culture, history, and stunning architecture. With over 47,000 participants from more than 100 countries, the marathon is a world-class event that’s full of energy, excitement, and inspiration. Bring the whole family to enjoy the festive atmosphere, support runners, and discover the city in a whole new way, all while helping raise funds for a variety of charitable causes.
No matter what your interests are, this weekend in Chicago has something for everyone: food, fun, movies, and exciting events to enjoy with friends or family. Get out there, explore the city, and make the most of all the fall festivities happening around town!
Curious about what was going on last weekend? Check them out here!