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60 exciting openings in Chicago in October

Written by
Grace Perry

After a weird, hot September, it looks like the weather is officially cooling down: Fall is here. As the spookiest month of the year, there are dozens of exciting new things to do in Chicago in October. From Halloween scares to family-friendly fun, you’ve got no excuse to hibernate just yet. It’s the most beautiful month of the year, so here are 60 exciting openings to take advantage of this October:


Oct 1: Sample more than 50 different beers from 20 breweries (okay, maybe don’t drink all of them) at the Logan Square Beer Festival.

Oct 1: Pig out on bacon and wash it down with local brews at the Bacon and Beer Classic at Soldier Field.  

Oct 1: Celebrate a Mexican Oktoberfest, aptly called Das Bueno Oktoberfest, at Rick Bayless’s brewery, Cruz Blanca Cerveceria.

Oct 1–30: Whether you’re afraid or heights or afraid of ghouls, Fright Fest at Six Flags Great America will scare you silly.

Oct 2: Eat the entire West Loop restaurant scene at once at the inaugural Fulton Market Harvest Fest.

Oct 4: Come hungry to OctoberFeast, a food and drink crawl through River North.

Oct 4–Dec 6: The Midwest Independent Film Festival kicks off in October and runs through the next two months at Landmark Theatres in Lakeview.

Oct 7: Take Oktoberfest to the next level by partying on a boat at Shoreline Sightseeing’s Oktoberfest Cruise.

Oct 7: Revel in fabulous fall flavors, sweet and savory, at Taste of Fall.

Oct 9: It’s a little late to start training, but cheer on runners both elite and recreational at the Bank of America Chicago Marathon.

Oct 13: See feminist trailblazer Gloria Steinem kick off this year’s Chicago Humanities Festival with a talk at Northwestern Law.

Oct 13: Turn an unassuming Loop alleyway into the wildest party of the fall as part of the Chicago Loop Alliance’s ACTIVATE series.

Oct 13: Bring an open mind and an empty stomach to Cook’s Science Live: The Burger Tour, where you’ll learn the quirkier side of food science.

Oct 13–23: Take advantage of Chicago’s cultural attractions with discounts, extended hours, special tours and more during Chicago Museum Week.

Oct 14 & 15: Sample (a selection of) 250 wines from around the world and attend talks with sommeliers at Wine Riot.

Oct 15: Take an adult field trip at Wild Spirits at Lincoln Park Zoo, where the zoo’s liquor variety will rival the its species variety.

Oct 15: Eat all the dumplings at Chicago’s first-ever dumpling fest, punnily titled Wrappers Delight.

Oct 15 & 16: Explore hidden architectural gems all across the city at Open House Chicago.

Oct 15 & 16: Hit up your favorite restaurants on wheels at The A.V. Club’s Logan Square Food Truck Social.

Oct 16: Taste nearly every Bloody Mary in Chicago at Bloody Mary Fest, where cocktail experts will battle for the title of Chicago’s Bloody Mary Master.

Oct 22: Celebrate the Field Museum’s latest exhibit, “TATTOO” with a drinks, bites and DJs at EVOLVE: Ink.

Oct 22: Go full, bloody Halloween at the 24-hour Massacre Horror Movie Marathon at Portage Park’s Patio Theater.

Oct 22: Take a creative spin on Halloween with the whole family at the Halloween Gathering in Millennium Park.

Oct 23: Train for the zombie apocalypse at the Monster Dash, which offers 5K, 10K and half-marathon road races.

Oct 27: Lincoln Park Zoo is spookier than you may think—learn about all of its paranormal phenomena from a ghost lore expert at Haunted Zoo Lecture.

Oct 28: See two hilarious writers bantering and interviewing each other at Abbi Jacobson in conversation with Samantha Irby.

Oct 28–Nov 7: Experience children’s stories from around the globe at the Chicago International Children's Film Festival.

Oct 31: Come dressed to impress (and scare) at the Northalsted Halloween Parade, where you’ll marvel at the crème de la crème of Halloween costumes.


Oct 1: Singer-songwriter Brian Wilson returns to Chicago to perform the Beach Boys classic Pet Sounds in its entirety.

Oct 5: Get ready to hear "Hotline Bling" for the umpteenth time as Drake brings his Summer Sixteen Tour back to the United Center.

Oct 5–9: Contemporary classical music takes the spotlight at the inaugural Ear Taxi Festival, which takes place at venues throughout the city.

Oct 7 & 8: Kanye West rides his floating stage to the United Center and Allstate Arena, for two hometown shows on his Saint Pablo Tour.

Oct 14: Join the mosh pit as local thrash metal act Oozing Wound celebrates the release of its latest album, Whatever Forever.

Oct 16: Multifaceted pop star Sia comes to the United Center with oversized wigs and dancer Maddie Ziegler in tow.

Oct 21: Singer-songwriter Cass McCombs will mash up folk, soul and smooth jazz from his latest LP, Mangy Love, during this stop at the Empty Bottle.

Oct 24: Celebrate the 10th anniversary of local shop Permanent Records with a free concert at the Empty Bottle, featuring Running, Counter Intuits and Matchess.

Oct 26: Get lost in the powerful falsetto and surreal melodies of Austin singer-songwriter Adam Torres, who comes to SPACE in Evanston.

Oct 28: Local 30-some piece marching band Mucca Pazza takes over Logan Square Auditorium with Balkan-style brass music and colorful costumes.

Oct 28–30: Put on a costume and dance the night away at Freaky Deaky, a three-day festival featuring Disclosure, DJ Snake, Tiësto, Schoolboy Q and more.

Oct 29: Rock and Roll Hall of Fame inductee Elvis Costello hits the Chicago Theatre with the Imposters, digging through his expansive catalog onstage.

Oct 30: Chicago-based rapper Lupe Fiasco plays a special concert at the House of Blues, where he'll hopefully debut some tracks from his final trilogy of albums.


Oct 20–Dec 23: See the stars of Nigeria's prolific film industry in "Nollywood Portraits: A Radical Beauty," which brings Iké Udé's glamorous portraits to the Museum of Contemporary Photography.

Oct 27–Jan 15: Cape Town artist Kemang Wa Lehulere explores what he calls "deleted scenes" of South Africa's history in the new Art Institute exhibition, "In All My Wildest Dreams."

Oct 29–Jan 8: Immersive video installation pioneer Diana Thater unleashes colorful, larger-than-life images at the Museum of Contemporary Art in "The Sympathetic Imagination."


Oct 1–Nov 20: A pregnant woman disappears from a small town in Ohio on Christmas Eve in A Life Extra Ordinary.

Oct 3–Nov 12: See How We Got On, a coming-of-age story about affluent suburban teens discovering hip-hop in the 1980s.

Oct 2–Nov 13: Catch Harold Pinter’s ominous drama, The Room, at A Red Orchid Theatre this month.

Oct 8–Nov 13: The New Colony is premiering a brand-new play called Merge, which tells the story of Atari (the video game company) in the 1970s.

Oct 8–22: The Burials, loosely based on Antigone, premieres as part of the Steppenwolf for Young Adults series.

Oct 19: Ever heard of a little show called Hamilton? It’s in previews now, but the show officially kicks off with opening night mid-October.


Oct 13–23: See choreographer Krzysztof Pastor’s retelling of Romeo and Juliet, set in 20th-century Italy to Sergei Prokofiev’s 1935 score.

Oct 13–15: See the Seldoms ensemble member Philip Elson’s multimedia piece about virtual disruption, The Seldoms: The Fifth.

Oct 28 & 29: See Giordano Dance Chicago’s Fall Series, a full-company piece by choreographer Peter Chu.


Oct 1–Nov 5: The Revival in Hyde Park explores chain reactions in its first sketch revue, Trigger.

Oct 1–Nov 19: Edgy sketch duo The Defiant Thomas Brothers broke up in 2006, but have reunited for a weekly show at Stage 773.

Oct 4–6: Game-changing standup comedian Louis C.K. is performing three nights at the Chicago Theatre—snag tickets if you can.

Oct 9: Daily Show correspondent Hasan Minhaj performs Homecoming King, his one-man show about growing up as a first-generation Indian American.

Oct 27–Oct 30: The Second City teams up with Lyric Opera for Longer! Louder! Wagner! The piece is tied into the Lyric’s reboot of Wagner’s Ring Cycle.


Oct: The Conrad Chicago will open up with three restaurants from Richard Sandoval (Latinicity), with executive chef Nathan Volz and executive pastry chef Anistar Griffith.

Oct 8: The long-awaited Flamingo Rum Club (the one with the colorful mural of Flamingos in River North) from Adolfo Garcia and Phil Stefani will open with a wide rum selection on October 8.

Note: Restaurant and bar openings are subject to change and can be delayed; call ahead before setting out.

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