Things to do in Chicago in October
· Updated · BootsnAll
October can be a lovely month in Chicago. The weekend neighborhood street festivals are over, and so are most of the summer tourists, but there's plenty to do before winter sets in. The farmers markets are still outdoors, the leaves turn, the city's biggest race and its biggest architecture festival both land this month, and the end of October brings Halloween, one of the best nights of the year for kids and adults alike.
Dates move from year to year, so we've listed when things usually happen and linked each event's own site. The city keeps a list of its festival dates on the DCASE dates page. For the weather, crowds and what to pack, see Chicago in October.
The big weekends
Chicago Marathon. The Chicago Marathon runs on a Sunday in early to mid-October, starting and finishing in Grant Park. It's one of the Abbott World Marathon Majors, and the course winds through 29 neighborhoods, so you don't need to be downtown to watch. Pick a spot near an L stop, bring a cowbell or a sign, and cheer for strangers. It's a better morning than it sounds. The race site has a spectator section with the course map and road closures.
Open House Chicago. For one weekend in mid-October, the Chicago Architecture Center offers behind-the-scenes access to more than 200 sites around the city, many of them normally closed to the public. It's free. The downside is lines at the famous downtown sites, which CAC members can skip with a priority pass. Our advice is to pick one or two neighborhoods outside the Loop and walk between sites. You'll see more and wait less.
Chicago International Film Festival. Founded in 1964 by filmmaker Michael Kutza, this is the longest-running competitive film festival in North America. It runs for about 12 days in mid to late October, with premieres, international competition films and plenty of directors in town for Q&As. The schedule and tickets are on the festival site.
Chicago Humanities. What used to be the Chicago Humanities Festival now runs a fall season from September through November, with dozens of talks, performances and conversations and a few Festival Days hosted by neighborhoods and universities. Popular talks can sell out, so check the Chicago Humanities lineup early.
Halloween
Arts in the Dark. The city's big downtown Halloween parade happens after dark on a Saturday in mid to late October. It's free and it's all about Chicago's arts groups, with giant puppets, dancers, musicians and floats. The route has moved between State Street in the Loop and Columbus Drive in Grant Park, so check Choose Chicago's parade guide for the current one. Get there early if you want a curb spot.
Haunted Halsted. The Haunted Halsted Halloween Parade in Northalsted, the Lakeview neighborhood at the center of gay Chicago, has been going for about 30 years. It's on or near Halloween night on Halsted Street, and the costumes are the whole point. A street fest usually runs during the day, and there's a costume contest after the parade. The Belmont and Addison Red Line stops are both a short walk away.
At the zoo. Lincoln Park Zoo is free every day of the year, and it throws an adults-only (21+) Halloween party in late October with drink sample stations. Tickets and dates are on the zoo's events calendar.
Día de los Muertos. Every fall the National Museum of Mexican Art in Pilsen puts up a Day of the Dead exhibition full of ofrendas and related art. Admission is always free. The museum is at 1852 W. 19th Street, near the 18th stop on the Pink Line. Have tacos on 18th Street afterward.
Leaves, apples and pumpkins
In the city, the trees in Lincoln Park and along the lakefront usually turn in the second half of the month. For a real leaf-peeping day, drive out to The Morton Arboretum in Lisle, a 1,700-acre tree museum that Joy Morton, the founder of Morton Salt, established in 1922. The arboretum's own staff say mid-to-late October is generally the best time, though it can shift a couple of weeks either way, and the Maple Collection is the one to head for. It's open from 9am to sunset, and the arboretum asks you to buy tickets online before you arrive.
Apple picking and pumpkin patches take a car. Two good ones are out past the western suburbs. Try Kuipers Family Farm in Maple Park, which has a U-pick orchard and a weekend pumpkin farm with shows and food trucks, and Jonamac Orchard in Malta, near DeKalb, which has apples, a pumpkin patch and a corn maze. The Sun-Times puts together an orchard guide most years. Go on a weekday if you can; weekends get crowded.
If you'd rather eat the harvest than pick it, Green City Market stays outdoors well past October. The Lincoln Park market (1817 N. Clark St.) runs Wednesdays and Saturdays from 7am to 1pm, and the West Loop market at 900 W. Monroe St. runs Saturdays from 8am to 1pm. See the market's site for the season's last day, and our list of farmers markets in Chicago.
Game day
The Bears are in the middle of their season at Soldier Field, and hockey and basketball both start up in October at the United Center, home of the Blackhawks and the Bulls. A Bears game is expensive and cold by November, so October is the friendlier month to go.
When it rains
October brings its share of gray, wet days. Head for the Garfield Park Conservatory on the West Side, which feels like summer under glass. It's free for Chicago residents and $10 for adults from out of town, and advance reservations are strongly recommended. The big museums are the other obvious move. We keep a list of free museum days (most are for Illinois residents), a guide to museums in Chicago and a page of things to do on rainy days. Evenings are good for theater, since the fall season is in full swing.
If the weather holds, the Chicago Architecture Center's river cruise runs from March through November. It's 90 minutes, tickets start at $57, and it's much easier to book in October than in July. More ideas in things to do in Chicago in fall and sightseeing tours in Chicago.
Photo by Brian L. Romig


