Chicago’s Best Street Festivals and Halloween Events In October

For us at the Ben Lalez Team, fall in Chicago always feels like the city at its best. We spend a lot of time around the city in every neighborhood, helping people find their homes, and every October, we look forward to some of the best events to happen during the year. It’s a great time to enjoy cooler weather and check out local festivals, parades, and block parties.

That’s why we put this list together. We’re not covering the big city-wide events, as we’ve previously written about these in our article Top Fall Events & Markets – September & October 2025. 

Instead, this article will be about street festivals, neighborhood events, Halloween celebrations, and fall festivities in Chicago. We don’t have a lot of time before winter hits us, so we hope you get a chance to get out and enjoy some of these events while you still can!

Lincoln Square Ravenswood Apple Fest

October 3–5, 2025 | Lincoln Avenue between Lawrence and Sunnyside

Apple Fest has been around for years, and we think it’s still one of the quickest reminders that fall is finally here. Lincoln Avenue fills with food stands, live folk music, and plenty of apple pie. You’ll find kids tugging at their parents for caramel apples and people lining up for hot cider. Local vendors bring out crafts, and there’s always a section of the street just for kids.

It’s free to walk in, though a small donation at the gate helps keep it going. We recommend bringing cash for quick transitions – the pies and cider sell out super quick!

Lincoln Park Wine Fest

October 3–5, 2025 | Jonquil Park, 1001 W. Wrightwood Ave.

For one weekend, Jonquil Park turns into an outdoor tasting room with Lincoln Park Wine Fest. Booths will line up around the park with wines from around the world, and what we love about this one is how relaxed it feels. You can talk with sommeliers if you want to have deeper discussions about wine with someone who’s actually studied it, or you can just enjoy live music while you sip.

Tickets are required, with options for general admission or VIP. General admission includes a glass and a set number of samples, while VIP gets you a little more. You’re best to grab tickets ahead of time because the sessions do sell out.

Historic Pullman House Tour

October 11–12, 2025 (expected dates) | Pullman National Historic District

This isn’t your typical festival, but the Historic Pullman House Tour is one of Chicago’s most interesting fall events. The Pullman neighborhood has been opening its doors for house tours for more than fifty years. What you’ll find is restored Victorian rowhouses, workers’ cottages, and historic landmarks like the Pullman Clock Tower and Hotel Florence.

Docents and residents share stories along the way, and you’ll learn a lot about the history of the area. We think it’s worth it if you enjoy seeing how Chicago’s past still shapes whole neighborhoods today. Tickets run about $30, and the proceeds go toward preservation.

Arts In The Dark Halloween Parade

October 18, 2025 | State Street, Downtown

Arts In The Dark might be our favorite Halloween parade in the city. It runs down State Street in the evening, and what you’ll see is glowing lanterns, massive puppets, and performers in surreal costumes. From zombie ballerinas to fire dancers, it’s always something different.

It starts early enough for families with kids, and it’s free to attend. You’re best to head down a little early if you want a good spot along the route.

Wicker Park Boo-Palooza And Bark-Palooza

October 18, 2025 | Wicker Park, 1425 N. Damen Ave.

This is a fun event that really brings everyone together. What we love is how the park feels packed with energy but never overwhelming. Your kids can decorate pumpkins, try a haunted maze, and join costume contests. Bark-Palooza is always a riot, because you get to see dogs walking around in costumes. You’ll definitely take some interesting pictures.

It’s free to attend, though donations are welcome. Bring a camera because the costumes, both human and canine, always make for good memories.

Roscoe Village Halloween Block Party

October 19, 2025 | Roscoe St. between Damen and Hoyne

Roscoe Village shuts down part of Roscoe Street for this block party. What you’ll find is plenty of trick-or-treating options for kids between businesses, people in costumes, and plenty of families bringing their pets along.

It’s free, and what we like most is how much it feels like a true neighborhood block party. If you can, come in costume, even if you don’t have kids. You might feel left out if you don’t.

Día De Los Muertos Xicágo

October 25, 2025 | National Museum of Mexican Art and Harrison Park, Pilsen

This event in Pilsen is one of the most meaningful celebrations of the season. There will be dozens of altars built by community members, live music, dance, food, and an illuminated altar projected onto the museum at night.

We think Día De Los Muertos Xicágo stands out because it’s not only a celebration, but also a way to honor tradition and family. It’s free to attend, and we recommend planning to be there for a few hours because there’s so much to take in.

Northalsted Halloween Parade (Haunted Halsted)

October 31, 2025 | Halsted St., from Belmont to Brompton

On Halloween night, Halsted turns into one of the biggest street parties in Chicago. The parade features costumes, floats, fire spinners, and drag performers, and what we love is that anyone can join.

It’s free to watch, but remember to register if you want to be part of the parade itself. After the contests and prizes wrap up, the neighborhood parties carry late into the night.

Jack’s Pumpkin Pop-Up

Sept. 18 – Nov. 2, 2025 | 1265 W. Le Moyne St., Goose Island

Jack’s Pumpkin Pop-Up mixes a pumpkin patch with a carnival. What you’ll find is a huge corn maze, thousands of pumpkins, carnival games, axe-throwing, food trucks, and bars. During the day, it’s family-friendly and at night, it turns into more of a hangout for adults.

Tickets start at around $25, and try to book early because popular times do sell out. Plan to spend a couple of hours here. It’s the closest you’ll get to a suburban pumpkin farm without leaving the city.

Pier Pumpkin Lights At Navy Pier

October 1–31, 2025 | Navy Pier, 600 E. Grand Ave.

For all of October, Navy Pier fills its walkways with hundreds of carved pumpkins lit up at night. You’ll find themed displays, trick-or-treating stations, and food vendors selling seasonal snacks.

It’s free, and we think it’s one of the easiest stops to add to a night downtown. You’re best to go after sunset so you can see the pumpkins glowing against the lake and skyline.

Wrapping Up

That’s our list. 

We know it’s hard to believe we’re already talking about Halloween costumes and pumpkin patches when it feels like summer just ended. What we like about this season, though, is that every neighborhood gives you a reason to get outside one more time before winter locks us in. 

We hope this list helps you make the most of October. At the Ben Lalez Team, we’re always up for a conversation about Chicago, and yes, we’ll probably be sipping cider while we do it. We’ll see you out there this fall!