We know you don’t want to hear this, but as we head into the last month of summer in Chicago, the fall season is right around the corner. But don’t worry, because there are still a ton of festivals, markets, and cultural events to enjoy!
From food fairs and music festivals to neighborhood celebrations and Halloween parades, we’ve compiled a list of some of the top events and seasonal markets happening around Chicago in September and October 2025, along with dates, locations, and highlights. Each event name links to a source where you can find more details.
We’re the Ben Lalez Team, and while you’ll find us busy helping buyers and sellers looking to make a move, we’re also excited ambassadors of Chicago, and we’re always enjoying everything the city has to offer.
We hope this list fills your fall months with fun experiences!
September 2025: Can’t-Miss Events & Markets
Taste of Chicago (Sept 5–7, 2025)
The city’s iconic food festival returns to Grant Park (Buckingham Fountain) and will be celebrating its 45th year! There will be lots of Chicago’s best eateries and food trucks selling some of the best cuisine, and admission to the festival is free. You can listen to live music on multiple stages (headliners include Lupe Fiasco and pop singer JoJo) as you munch on deep-dish pizza and gourmet tacos. For more info, visit the official Taste of Chicago page.
Chicago German-American Oktoberfest (Sept 5–7, 2025)
Come experience an early Oktoberfest celebration in Lincoln Square in September! This weekend-long German festival features the very best of traditional bratwurst, pretzels, and beer. Of course, what is Oktoberfest without live German bands and dancing under big tents? There will also be the Von Steuben Parade on Saturday at 2pm. The fest is family-friendly (carnival games and rides for kids) and admission is free. For more details, check out the event’s website.
Renegade Craft Fair (Sept 6–7, 2025)
A fun street market in Wicker Park, Renegade is a fair featuring handmade goods from hundreds of craftspeople. It’s a good place to find one-of-a-kind art, home decor, apparel, jewelry, and food. Entry is free, and you’ll enjoy DJs and food trucks. It’s a great chance to support independent artists and find unique treasures. Check out Renegade Craft’s website for a vendor list and schedule.
Riot Fest (Sept 19–21, 2025)
Riot Fest is a 3 day music festival at Douglass Park celebrating its 20th anniversary, and is known for rock, punk, and alternative lineups. This year, acts include Blink-182 (Friday), Weezer & Jack White (Saturday), and Green Day (Sunday)! You can expect carnival rides, lots of band merchandise to buy, and music across multiple stages. This is a ticketed event (not free), so if you want to attend, make sure to visit the official Riot Fest site.
Chicago Gourmet (Sept 25–28, 2025)
Chicago Gourmet is a 4 day upscale food and wine festival where top chefs, restaurants, and drink experts come together to show off their talents. It will be held at the Harris Theater rooftop in Millennium Park, and events include tastings, cooking demos, the Hamburger Hop competition, and the Grand Cru tasting (fine wines paired with gourmet bites). This year’s theme is “Step Up to the Plate,” blending food with sports culture. Tickets are required for most events, so check the Chicago Gourmet website for schedules and passes.
St. Alphonsus Oktoberfest Chicago (Sept 26-28, 2025)
Wait a second… another Oktoberfest festival? Why not! This one is located in Lakeview at the intersection of Lincoln, Wellington & Southport (outside St. Alphonsus Church). This popular street festival brings Bavaria to Chicago with steins of beer, classic German food, and two stages of music. There’s a “Kinderfest” area on Sunday for families with kids. Admission is a suggested $10 donation on Fri/Sat (Sunday is typically free or donation-based). More details on the Oktoberfest Chicago can be found here.
Hyde Park Jazz Festival (Sept 27–28, 2025)
A free jazz music festival in its 19th year on the South Side, covering venues around Hyde Park (including the Midway Plaisance and local performance spaces). Over the weekend, you can enjoy dozens of live jazz performances from local and international artists. Stages are spread out (both outdoors and indoors), and all performances are open to the public. We recommend bringing a blanket or chair to enjoy the festival! More information can be found on their website.
Randolph Street Market Festival (Sept 27–28, 2025)
This is a well-known vintage and antiques market located at 1341 W. Randolph Street in the West Loop, and is known as one of America’s top urban markets. It’s a European-style bazaar featuring over 300 vendors selling everything from mid-century furniture and retro fashion to rare collectibles and vinyl records. It’s both indoor and outdoor, with food vendors and a beer garden. Tickets are about $10 (with discounts for students; kids 12 and under are free). It’s worth checking out if you love treasure-hunting for unique finds. See their official site for hours and ticket info.
Lincoln Park Zoo Fall Fest (late Sept – Oct, 2025)
Starting in late September and all through October, the Lincoln Park Zoo brings back its annual Fall Fest. This free event (open Fridays through Sundays) features a pumpkin patch, hay mountain, corn maze, and fall decorations to officially signal the end of summer. Families can enjoy live music, watch professional pumpkin carvers, and even see the zoo animals get special pumpkin treats. For a small fee, there are additional attractions like haunted houses, carnival rides, and pumpkin carving workshops. Each weekend offers something a little different, so check the details on dates and activities on the Lincoln Park Zoo’s Fall Fest page before you head out.
October 2025: Fall Festivals, Culture & Halloween Fun
Lincoln Square Apple Fest (Oct 3–5, 2025)
This will be Apple Fest’s 38th annual event and is located in the heart of Lincoln Square on Lincoln Ave between Lawrence and Sunnyside. As the name suggests, this event celebrates everything that has to do with apples. You’ll find the freshest farm apples, hot apple cider, apple pies and donuts, and other apple treats. There’s live folk and bluegrass music, local crafts, and activities for the kids. A $5 suggested donation is appreciated at the gate. More info can be found via the Lincoln Square Ravenswood Chamber of Commerce website.
Bank of America Chicago Marathon (Oct 12, 2025)
One of the world’s great marathon races takes over Chicago’s streets on Sunday, Oct 12th, and it starts and ends in Grant Park. The Chicago Marathon runs 26.2 miles through a bunch of Chicago neighborhoods in front of huge crowds. About 40,000 runners from across the world are expected to participate. The race starts around 7:30am, and expect the streets along the route to be closed to traffic. You can watch the event for free and take in the incredible energy (look out for runners in costumes, live bands, and cheer zones!). For course maps or to track runners, visit the official Chicago Marathon website.
Chicago International Film Festival (Oct 15–26, 2025)
The 61st annual Chicago International Film Festival is coming again, and as North America’s longest-running competitive film fest, it’ll bring over 100+ films across various theaters in the city. If you’re a film buff, you can expect a mix of feature films, documentaries, shorts, and premieres (with filmmakers and stars making appearances). You can buy festival passes or individual tickets (some screenings and events may be free or discounted for students). This is the perfect chance to catch award-winning films and up-and-coming directors before they hit wide release. See the Chicago Film Festival’s site for the full schedule and tickets.
Open House Chicago (Oct 18–19, 2025)
Open House Chicago is an architecture festival by the Chicago Architecture Center, offering behind-the-scenes access to 150+ sites citywide, including historic buildings, skyscraper offices, members-only clubs, theaters, churches, and hidden architectural wonders. You can create your own self-guided tour across more than 20 neighborhoods, from exploring normally-closed areas of famous downtown towers to discovering beautiful spaces in neighborhoods like Bronzeville, Rogers Park, or Little Village. It’s one of the largest events of its kind in the world. No tickets are required, so just check the site list and go (some popular spots may have lines). Visit CAC’s Open House Chicago page for site lists and an interactive map.
Arts in the Dark Halloween Parade (Oct 18, 2025)
The Arts in the Dark is a nighttime parade that marches down State Street in the Loop starting at around 6pm. This is a free, family-friendly experience full of lights, costumes, and music. You’ll see giant illuminated puppets, parade floats designed by local artists, dance groups in funky outfits, and lots of talented performers. Now in its 11th year, it usually attracts over 60,000 spectators to the Loop. It’s an only-in-Chicago event that treats Halloween as “the artists’ holiday.” Arrive early to grab a good viewing spot along State Street! More information is available on the Arts in the Dark website.
Pier Pumpkin Lights at Navy Pier (Oct 1–31, 2025)
All through the month of October, head to Navy Pier for Pier Pumpkin Lights, a free pumpkin pop-up experience when the entire Pier gets decorated with close to 1,000 hand-painted pumpkins and larger-than-life light installations. You’ll find themed pumpkin zones, pumpkin towers, glowing jack-o’-lantern tunnels, and other artsy displays both indoors and outdoors. There are some fantastic photo opportunities here, especially when the sun sets and the pumpkins light up and reflect off Lake Michigan. While you’re there, you can also enjoy Navy Pier’s other fall festivities, like trick-or-treating events for kids or Halloween-themed rides. Pier Pumpkin Lights is open every day. Just check Navy Pier’s event calendar for all Halloween events.
Haunted Halsted Halloween Parade (Oct 31, 2025)
The best way to end October is with Chicago’s biggest Halloween night event: the Haunted Halsted Parade in Northalsted (Boystown). Starting at 6:3pm on Halloween night, this over-the-top costume parade marches down Halsted Street and you’ll get to see Chicago’s most creative, outrageous, and spooky costumes. The parade is free to watch and has been ranked among the top 10 Halloween celebrations in America. If you (or your pet) show up in costume, you can join in and compete in the famous costume contest, which offers $4,000 in cash prizes across different categories like Best Group, Scariest, Most Creative, etc. The parade will feature flamboyant floats, drag queens, live DJs, and you’re guaranteed to have a lot of fun. After the parade and awards show, many nearby bars and clubs will host themed parties to keep the fun going all night. This parade is a uniquely Chicago experience on Halloween, so don’t miss it! For details or to register for the contest, visit the Northalsted parade page.
Final Thoughts
Well, that’s it. It’s tough to be talking about autumn events so soon because it’s just a reminder that summer is slipping away. For some of you, this summer has brought on some of the hottest and most humid days we’ve had in recent years.
Maybe fall’s cooler weather will be refreshing and a nice change from the heat waves before we get ready for Chicago’s brutal winter. In the meantime, if you’re thinking about making a move this fall and need some insights into the best neighborhoods to check out, give us a shout! We’ll be happy to share our thoughts over a pumpkin-flavored latte and brag about our love of Chicago!