Everything Fun to Do in Chicago This October, from Beer Fests to a Pumpkin Pop-Up
These are all your local must-hit music and food festivals, events, movies, markets, deals, and concerts to help you make the most of your weekend.
Fall in Chicago is here. Leaves are gently falling from trees, and streets are filling with be-flanneled Chicagoans trying to not think about the fact that we’re only a few short months from the next polar vortex. There’s plenty to do this fall, whether you want to check out the city’s best restaurants, browse the final days of a local farmer’s market, or have a romantic night out with your partner.
Chicago has something to offer everyone, from state parks to thrift shops to pop-ups. And if that’s not enough for you, it’s also well within driving distance of some wonderful day trip spots. Whether you want to hit the trails, relax at a spa, or test your friendship at one of our city’s escape rooms, the City of Broad Shoulders has you more than covered.
Knowing all this, it should come as no surprise that there are plenty of weekend outings that are worth your time this October. Here are some of our can’t-miss favorites.
Festival Events in Chicago
October 7 - 8
North Center, $5 Suggested Donation
Two of Chicago’s most beloved breweries are joining forces once again to host a full-on festival celebrating all things fall. Dovetail and Begyle have teamed up for two days of live music, great food, and, of course, tons of beer. Bring your favorite light jacket and toast Begyle’s 11th anniversary with a Blonde ale.
October 11 - 22
Multiple locations, Single film tickets start at $22
Featuring over 100 films and 60 shorts across Chicago’s most beloved theaters and gathering spaces (The Music Box, AMC Newcity 14, the Gene Siskel Film Center, the Harrison Park Fieldhouse, among others), there isn’t a much better way to spend a weekend. Bundled ticket sales are available as well, so grab a buddy, order an irresponsible amount of popcorn, and make your own movie marathon.
Food & Drink Events in Chicago
September 30 - October 1
Lincoln Square
$5 suggested donation
What better way to ring in Fall than a harvest festival? Apple Fest will feature over 50 vendors and farms slinging ciders, pies, and Fall wares. Grab your favorite red flannel shirt, grab a pumpkin spice latte on the way, and celebrate all the flavors of the season.
October 6 - 8
Jonquil Park, Starting at $35 for early bird tickets
Hop down Wrightwood to see Jonquil Park transformed into an open-air market full of food, drink, and art vendors. Your ticket will include 12 tastings over a two-hour period, so remember to pace yourself.
October 7
The Field Museum, Tickets start at $50
Over 65 brewers will descend upon The Field Museum for this year’s Chicago Beer Fest, a celebration of all things hoppy, malty, and delicious. Make sure to get your tickets in advance—they’re not available at the door—and settle in, because admission includes 40 taster vouchers. Stay hydrated, you wouldn’t want to be too sloshed in Sue’s presence, would you?
October 7 - 8
La Bagh Woods, Free
If you missed the summer version of this festival, you’re in luck: there’s a fall festival too. Come celebrate the proud tradition of the food truck, complete with yard games, cold beers, and live music. This is the festival’s tenth season, and they’re celebrating with a bang, bringing together the most diverse lineup of food trucks the city has ever seen. No matter what you’re in the mood for, whether it’s lobster, tacos, ribs, jerk chicken, or overstuffed sandwiches, your appetite will be sated by Chicago’s mavens of mobile mastication. And yes, Harold’s Chicken will be there too.
Art & Entertainment Events in Chicago
Friday - Sunday through October 29
Lincoln Park, Free
Though the Fall Fest is open all week (with ghost tours on Tuesdays and Wednesdays and a can’t-miss Adult’s Night Out Halloween party on Thursday the 26th), we couldn’t in good conscience not include this free event that features stilt walkers, pop-up bars, a pumpkin patch, and a variety of (ticketed) rides and attractions.
October 7 - 8
Pullman, Tickets start at $20
The Pullman neighborhood is a National Historical Park. Yep. The whole neighborhood. It’s that big of a deal. The town began its life as a company town meant to entice workers to move there to build rail cars. After the Pullman Strike, Pullman was absorbed into Chicago proper, and since then the original rowhouses built by George Pullman have been protected and preserved as historical landmarks. This year marks the 50th anniversary of the Pullman House Tour weekend, which invites everyone to come and view the best-preserved homes of the era, and learn more about this slice of history.
Through November 12
Multiple Locations, Ticket prices vary
Destinos, the Chicago International Latino Theater Festival descends on Chicago for the sixth year running this fall, featuring can’t-miss plays and productions at some of the city’s most beloved theatrical spaces. From a lucha libre-inspired production that promises to turn Theatre Goodman into a fully-fledged wrestling arena to a black comedy steeped in magical realism and the traditions of the Yucatán Peninsula, there are few better ways to spend a fall evening in Chicago.
October 8
Grant Park, Free to spectate
It’s almost time for Chicago’s most aspirational event—and while registration for this year’s race ended almost a year ago, you can still wake up early to support racers along the race route, and meet up with runners at the afterparty in Grant Park. Not a bad way to spend a Sunday.
October 28
Congress Plaza Hotel, Tickets start at $30
There’s no shortage of ways to celebrate Halloween in Chicago, but if you want to show off your costume at the biggest Halloween party in the city, there’s only one choice. The Haunted Halloween Ball will take over the famously haunted Congress Plaza Hotel, transforming it into an abandoned inn run by party-loving zombies. DJs will be spinning dance-worthy tunes all night, providing a soundtrack for encounters with vampire bellhops, performances by costumed go-go dancers, and, of course, a costume contest (with a $2,000 cash prize).
Through November 5
Goose Island, Tickets start at $22
Jack’s Pumpkin Pop-up is a perennial spooky season favorite and for good reason. Axe throwing, a corn maze (which, in the past, featured a secret bar only accessible to people who solve it), photo ops, fortune tellers, and of course, a ton of pumpkins ready for you to take home and carve up. It’s a yearly must—which makes it worth deciphering the arcane multi-tiered ticketing system.