Autumn in Chicago is arguably the best time to enjoy the city. The ‘L’ tracks aren’t frozen over and the smothering summer humidity has finally dissipated. Autumn weather in Chicago is usually mild, breezy and perfect for exploring. Luckily, the city has plenty to offer on the weekends during this temperate time. 

“September and October is really the only time I want to be outside,” said part-time DePaul student Katie Kaberlein, 19. “There’s always festivals going on too, which is the best.”

Many of the events going on in the upcoming months are perfect for Chicago’s college students, as there are little to no age restrictions.  

“I would definitely recommend the Japanese Matsuri,” said Loyola University sophomore Sydney Pochatek, 19. “I’m excited to go back this year since it’s in a bigger location.” 

These are Chicagoland events for longtime residents and newcomers alike interested in stepping out on the weekends, depending on what you’re interested in: food, culture, or arts and antiques. 

What’s A Diet?  

Dessert Fest at Lincoln Park Zoo

When: September 14, 6:30 pm to 11 pm 

Where: Lincoln Park Zoo, 2001 N. Clark Street

Push your sweet tooth to the limit at this delicious event. Chicago’s favorite confectionaries such as Stan’s Donuts, Bittersweet and Chimney Cone Creamery are setting up tasting tables at the Lincoln Park Zoo for guests to enjoy.  Early-bird tickets cost $25 and most of the proceeds will go towards the zoo, which helps it remain free all year. 

https://dessertfestatthezoo.eventbrite.com/?aff=lpz

Green City Farmer’s Market in Lincoln Park

When: Wednesdays and Saturdays until October 19

Where: 1817 N. Clark Street

Need a nice stroll after brunch? This adorable farmer’s market, located in Lincoln Park, is a great weekend stop. Take a group of friends and try some wacky preserves, or try your hand at “adult life” by buying all-organic groceries. Dogs are welcome, by the way, so you’ll definitely get to pet some four-legged friends while you’re there. 

Apple Festival 

When: October 5-6, 9 am to 6 pm

Where: Lincoln Avenue between Lawrence Avenue and Eastwood Avenue (Lincoln Square Neighborhood) 

This one will really help you get in the fall mood. The Lincoln Square Ravenswood Apple Fest is an outdoor street fair perfect for showing off your chunkiest knit sweater. Apple themed food, drink and games are a plenty as dozens of Chicago vendors set up shop with apple-themed menus. 

Get Cultured 

Palestine at the Park

When: September 14, 2 pm to 7:30 pm

Where: 7729 Ogden Avenue, Lyons IL

DePaul’s Students for Justice in Palestine (SJP) organization is hosting this event to celebrate all things Palestinian. People ages 18-30 are welcome to enjoy a traditional Sahra, a Palestinian party typically thrown before weddings.

St. Al’s Oktoberfest

When: September 27-29 ($10 Fri-Sat, $5 Sun) 

Where: 1429 W. Wellington Ave

A weekend of traditional German fun, food, and music located at St. Alphonsus Church in the nearby Lakeview neighborhood. 

All ages until 5pm, 21+ after 5pm 

Kizuki Chicago Japanese Matsuri 

When: September 20-22

Where: NEWCITY Center, 1457 N. Halsted St.

After achieving a massive turnout at last year’s first Matsuri, Kizuki Ramen & Izakaya and the Japanese Cultural Center are ready to host the second coming of this cultural fair. Matsuri is the Japanese word for festival, typically held outside and during the end of summer, in order to celebrate the coming harvest. This event, held in 100,000 square feet of NEWCITY’s indoor and outdoor space, will boast two floors of traditional food, dance, art and demonstrations as well as shopping, games and a cosplay contest.

The Arts

Lakeview East Arts Fair

Where: Along Broadway from Belmont Avenue to Hawthorne Place

When: September 14 until 10 pm, September 15 until 6 pm 

Immerse yourself in Chicago’s art scene by perusing the works of over 150 specially selected artists. Along with the art, enjoy live music and demonstrations, as well as a garden oasis.

Ravenswood Art Walk

Where: Along Ravenswood Ave. from Irving Park Rd. to Leland Avenue

When:  September 14-15, 11 am to 6 pm 

This arts festival in the eclectic Ravenswood neighborhood has artist booths as well as live music, a beer garden, food trucks and a children’s activity center. 

Randolph Street Flea Market

When: September 28-29, 10 am to 5 pm 

Where: 1341 W Randolph Street

Go antiquing in Chicago’s West Loop region for unique finds. The Randolph Street Market has some of the “best decor scores in the city” according to Timeout Magazine. General Admission is $8 online and $10 at the door. 

Header Image by Ava O’Malley