Things to do in Chicago this Fall 2025 + Parking tips

Explore the best things to do in Chicago in Fall 2025. Enjoy seasonal and local events, plus get tips for finding parking nearby without the stress.

Fall in Chicago is one of the best times to explore the city. The summer crowds thin out, the weather becomes cooler, and the streets fill with everything from food festivals to cultural events. If you’re looking for something new to do or planning a weekend getaway, Chicago’s fall calendar is packed with things to do. From neighborhood festivals to big-name concerts and scenic walks, fall offers a wide variety of events and seasonal activities across the city.

Top Things to Do in Chicago This Fall 2025

Fall in Chicago is packed with exciting events and activities. Here are a few you may want to check out for yourself:

September Highlights

What: Taste of Chicago
When: September 5 to 7
Where: Grant Park
One of the city’s biggest food events returns to Grant Park. Taste of Chicago features local restaurants, food trucks, live performances from local and international music artists, and family-friendly activities. Admission is free, but food and drinks are not, so don’t forget to bring cash or a card.

Parking Tip: Spots fill up fast during this popular downtown event, so reserve parking near Grant Park early. Some nearby garages also offer special event rates, so be on the lookout for deals.

What: Chicago German-American Oktoberfest
When: September 5 to 7
Where: Lincoln Square
This popular event offers traditional German beer, pretzels, plenty of bratwurst (among others), carnival games, and a lineup of German bands. There’s also a parade happening along Lincoln Avenue on Saturday (September 6) at 2 PM.

Parking tip: Street parking is limited in Lincoln Square during festivals, so you’ll have to consider off-street parking instead. However, if you’re planning to drink or have other plans after your visit, it’s best to use public transportation instead to avoid driving under the influence.

What: Englewood Jazz Festival
When: September 18 to 20
Where: Hamilton Park and Cultural Center
A three-day, free jazz festival on Chicago’s South Side, the 26th Englewood Jazz Festival also celebrates the 60th anniversary of the Association for the Advancement of Creative Musicians (AACM). Expect performances from top Jazz performers including Ernest Dawkins, Renée Baker, Adegoke Steve Colson, JoVia Armstrong and many more. The festival kicks off indoors on Thursday and Friday, but performances will extend outdoors on Saturday regardless of weather.

Parking tip: Free parking may be available at Hamilton Park, but spaces are limited so arrive early.

What: Riot Fest
When: September 19 to 21
Where: Douglass Park
In celebration of its 20th year, Riot Fest is bringing major headliners to Douglass Park, such as Green Day, Blink-182, and The Smashing Pumpkins. For fans of rock, punk, or alternative, Riot Fest is definitely the place to be this fall.

Parking Tip: Street parking around Douglass Park is extremely limited during Riot Fest, but if you plan to drive, consider booking a parking spot in advance.

October Attractions

What: Chicago Marathon
When: October 12
Where: Grant Park (Start/Finish Line)
Come out to watch and cheer as thousands of runners take on 26.2 miles through 29 Chicago neighborhoods and towards the finish line at Grant Park. Even if you’re not running, you can enjoy the excitement and competitive atmosphere along the marathon course.

Parking Tip: Expect extensive street closures near Grant Park and along the race route. Consider public transport instead.

What: Chicago International Film Festival (CIFF)
When: October 15 to 26
Where: Screening venues vary

Buy your passes now and watch both local and international feature films, documentaries, and shorts at the 61st CIFF – the nation’s longest-running film festival. Screenings are held in cinemas across the city, and you can buy multiple screening passes or single tickets and simply enjoy the festival hotspots afterward.
Parking Tip: Venues vary, but many screenings are downtown or on the North Side. It’s best to confirm which cinema you’ll be viewing at then plan your parking from there.

What: Arts in the Dark
When: October 18, 6 to 8 PM
Where: State Street (Lake Street to Van Buren)

Come out to the streets and enjoy the artistic and festive atmosphere of the Arts in the Dark Parade! Find the best viewing spot along the parade route on State Street from Lake Street to Van Buren. The parade may only be for two hours, but it’s two hours of unique and spectacular floats, puppets, and amazing performances that’s sure to bewitch both the young and young-at-heart.

Parking Tip: Parade night draws big crowds and street closures along State Street. Consider parking farther away and using public transportation or walking to the parade route.

November Events

What: 312 Comedy Festival
When: November 4 to 9
Where: Venue varies

Enjoy nights of laughter as more than 20 top stand-up comedians take the stage across six Chicago venues. Tickets for individual performances are available from the 312 Comedy Festival website.

Parking Tip: performance venues vary, so check each location in advance when you plan your route and parking.

What: Festival of Wood & Barrel-Aged Beer (FoBAB)
When: November 7 and 8
Where: UIC Credit Union 1 Arena

Craft beer fans rejoice once again as FoBAB brings together breweries from across the country for a weekend dedicated to barrel-aged stouts, sours, and more. Make sure to buy your ticket at the FoBAB website before heading over to the UIC Credit Union 1 Arena. I’m a Big Illinois Beer Enthusiast (ImBIBE) members may also buy VIP tickets and enter the venue one hour ahead of the crowd.

Parking Tip: Parking near the venue can be scarce during major events, but UIC Credit Union 1 Arena operates a parking garage beside the building and two fenced parking lots across the street. Event parking rates range from $10 to $20 depending on the event, but you may contact them to confirm the actual price for the event you’re attending.

What: Chicago Thanksgiving Parade
When: November 27, 8 to 11 AM
A beloved Chicago tradition, the Chicago Thanksgiving Parade has been held every Thanksgiving morning since the 1930s. This free, family-friendly event takes over State Street from Ida B. Wells Drive to Randolph Street and features marching bands, equestrian units, festive floats, giant inflatable balloons, and cultural performance troupes. But don’t worry if you can’t make it to the streets because the parade will also be broadcast live on Pluto TV.

Parking tip: Expect major road closures along State Street, so check the route before heading out and consider parking farther away and using public transport or walking to the parade route instead.

Chicago Fall Activities You Can’t Miss

While there are medium- and large-scale events happening in Chicago in Fall, there are also activities you can enjoy if you don’t want to be surrounded by large crowds or don’t have much time to spare. Here are some quick activities you may enjoy in Chicago this fall:

• Apple Picking
  Just an hour or two away, Apple orchards like Jonamac, Royal Oak Farm, and Goebbert’s offer fresh apples, hayrides, cider donuts, and fall photo ops.
• Haunted Houses and Ghost Tours
  Halloween fans and occult enthusiasts can enjoy plenty of haunted attractions around Chicago. Take a guided ghost tour downtown for a mix of history and spooky storytelling.
• Scenic Fall Walks
  For great views of the fall colors, head to the Riverwalk, Lincoln Park, or the Chicago Botanic Garden. There’s also the Morton Arboretum in Lisle if you’re up for a short drive.

Parking Tips for Fall Events in Chicago

Parking in Chicago can be tricky, especially during major fall events when traffic increases and street closures are common. If you’re planning to attend festivals like Taste of Chicago, the Chicago Marathon, or the Thanksgiving Parade, make sure to research parking options and check for road closure announcements ahead of time.

Many garages offer event rates, but they can fill up fast when citywide and popular events happen. Check garage websites for rate changes and if you can reserve parking in advance. By planning ahead, you can save time and money, and avoid parking stress on the event day.

Book Parking in Chicago with Spacer

Attending a festival or event in Chicago this Fall? Book a parking spot ahead of time with Spacer. Whether you’re looking for parking in Lincoln Square, Hamilton Park, or Downtown Chicago, Spacer makes it easy to book secure, reliable, and affordable parking in advance, so you can focus on fun instead of circling the block.