Chicago isn’t only about summer street festivals and lakefront fun. The city also has incredible things to do in Chicago during the fall!
Chicago fall festivals are celebrations in food, culture, and community, giving you so many reasons to put on your favorite sweater for this weather and step outside for something exciting. Honestly, this is why, besides spring, this is my favorite time for events in Chicago throughout the year.
If you’re looking for the best Chicago festivals 2025 or want to plan your list of things to do in Chicago this fall, I’ve rounded up the must-attend events for September and October.
Below are a few standout Chicago neighborhood festivals for 2025 worth adding to your calendar. Want even more? Don’t miss the full list of Chicago fall festivals here.
The Best Fall Festivals in Chicago 2025
Chicago Humanities Festival | Fall 2025
Dates: September–November 2025
Location: Multiple Venues | Chicago
Price: Free & Ticketed Events
The Chicago Humanities Festival returns this fall with a robust lineup of conversations, performances, and cultural activations designed to explore what it means to be human. Programming spans from Latino-centric events at the National Museum of Mexican Art to Humanities Day at the University of Chicago, featuring world-class thinkers, artists, and cultural leaders. Hear from voices like Roxane Gay, Nick Offerman, Robin Givhan, Nate Silver, and many more. Beyond talks, visitors can engage with free public art installations, mariachi performances, neighborhood tours, and collaborations with institutions like the Lyric Opera of Chicago. This season, CHF continues to celebrate curiosity, creativity, and culture through events that bridge history, community, and contemporary life.
79th Street Renaissance Festival
Dates: September 6, 2025
Location: Auburn Gresham | South Side
Price: Free Entry
One of Chicago’s longest-running neighborhood festivals, the 79th Street Renaissance Festival celebrates local culture, food, and community. Enjoy live performances, local vendors, family-friendly activities, and neighborhood pride at this South Side Chicago fall festival.
Taste of Chicago
Dates: September 12–14, 2025
Location: Grant Park | The Loop
Price: Free Entry, food and drink tickets available for purchase
The city’s most iconic food festival returns to Grant Park, showcasing Chicago’s incredible and diverse culinary scene. Dozens of vendors, food trucks, and live music performances from top artists make this a must-attend for foodies, families, and music lovers. Neighborhood pop-ups offer mini Taste experiences for those who can’t make it to the main event.
Hyde Park Jazz Festival
Dates: September 27–28, 2025
Location: Hyde Park | South Side
Price: Free Entry (donations encouraged)
Celebrate Chicago’s rich jazz heritage with local and international artists across multiple venues in Hyde Park. This Chicago music festival features intimate stages and outdoor spaces, offering a full weekend of music and cultural experiences for jazz enthusiasts.
Chicago Gourmet
Dates: September 25–28, 2025
Location: Millennium Park | The Loop
Price: Ticketed Event
Chicago Gourmet is a high-end culinary experience featuring top chefs, mixologists, and sommeliers. Guests can enjoy tastings, demonstrations, and curated dining events, all designed to take attendees on a global culinary journey in the heart of the city.
Haute Tip: Many events offer early-bird tickets and season passes. Set calendar reminders a few months ahead for the best deals.
Oktoberfest Chicago
Dates: September 26–28, 2025
Location: St. Alphonsus Church | Lakeview
Price: $10 Entry
Celebrate Bavarian traditions with beer, brats, and live music at Oktoberfest Chicago. The festival spans the church and surrounding streets, providing a full weekend of seasonal celebration and community fun.
Journey Chicago
Dates: October 2025
Location: Citywide | Various Neighborhoods
Price: Varies by event, many free options
Journey Chicago is a citywide, intercultural festival of art, ideas, and performance. With dozens of partner organizations, the family-friendly festival highlights the cultural diversity of Chicago through talks, exhibitions, and live performances across neighborhoods throughout October.
The 61st Chicago International Film Festival
Dates: October 15–26, 2025
Location: Multiple Theaters & Venues | Chicago
Price: Varies by Event
Now in its 61st year, the Chicago International Film Festival is North America’s longest-running competitive film festival, bringing global cinema to the heart of the city. Audiences can expect an extraordinary lineup of dramas, thrillers, documentaries, comedies, and more, featuring programs such as Black Perspectives, OutLook, International Comedy, After Dark, and City & State, which spotlight Illinois filmmakers. Featuring in-person screenings with select films presented with closed captions, the Festival is an essential experience for cinephiles seeking both fresh voices and acclaimed works from around the world.
Lincoln Park Wine Fest
Dates: October 3–5, 2025
Location: Jonquil Park | Lincoln Park
Price: $40–$109
Sample wines from around the world at Lincoln Park Wine Fest, a Chicago wine festival right in the city. The park is transformed into an open-air tasting pavilion with global varietals, live music, and food pairings. Perfect for anyone looking for a relaxed fall outing.
Apple Fest
Dates: October 4–5, 2025
Location: Lincoln Square | Lincoln Square Ravenswood
Price: $5 Suggested Donation
Kick off the season at Lincoln Square’s Apple Fest, featuring apple-inspired treats, local cider, baked goods, and seasonal goods. Live music and family-friendly activities make this a beloved neighborhood tradition for all ages.
Chicago Beer Fest
Dates: October 4, 2025
Location: The Field Museum | Museum Campus
Price: General $65 | Early Entry $80 (includes specialty beers in first hour)
Sip seasonal beers at one of Chicago’s most unique venues. The Chicago Beer Festival features over 65 breweries serving fall favorites in a one-of-a-kind museum setting. Early entry includes an extra hour with specialty pours, and attendees receive taster vouchers for a curated experience.
Chicago Fashion Week® 2025
Dates: October 9–19, 2025
Location: Multiple Venues | Downtown Chicago & Beyond
Price: Varies by Event
Chicago Fashion Week® returns this fall, bringing together designers, models, and creatives to showcase the city’s growing influence in global style. From emerging talent to established names, CHI✶FW celebrates fashion as both culture and couture, highlighting diverse perspectives and bold visions that define Chicago’s unique look. With events open to the public across the city, the week-long celebration invites audiences to experience runway shows, pop-ups, panels, and more—all designed to unite Chicagoans through fashion and creativity.
Open House Chicago
Dates: October 18–19, 2025
Location: Citywide | Various Neighborhoods
Price: Free Entry
Explore Chicago’s architectural treasures during Open House Chicago. The festival provides behind-the-scenes access to over 150 historic and culturally significant sites throughout the city. Visitors can enjoy self-guided tours, talks, and programming highlighting Chicago’s architectural and cultural history.
Arts in the Dark
Dates: October 18, 2025
Location: State Street | Downtown Chicago
Price: Free Entry
Arts in the Dark is a nighttime parade celebrating Halloween with large-scale puppets, illuminated floats, music, and dancers. The parade brings together artists and performers from across the city, creating a magical and family-friendly experience for all ages.
31st Annual Black Harvest Film Festival
Dates: November 7–16, 2025
Location: Gene Siskel Film Center | Chicago
Price: Varies by Event
Celebrating its 31st year, the Black Harvest Film Festival continues its tradition of amplifying Black voices and stories through the power of cinema. Showcasing short and feature-length films from across the diaspora, the festival highlights emerging creators alongside legendary auteurs. From historical narratives to groundbreaking contemporary stories, the lineup offers a profound exploration of Black identity and cultural expression. Held at the Gene Siskel Film Center, this annual showcase is a cornerstone of Chicago’s cultural calendar and a must-attend for film lovers.
