The best October 2026 events and things to do in Chicago

Every October, more than 45,000 runners hit the streets of Chicago and take a 26.2 mile tour of the city by foot. While it's too late to enter the race (and complete months of grueling training), you can join tens of thousands of spectators on the city's streets to cheer on participants as they make their way through the course. The start and finish line in Grant Park isn't open to the public, but you can head to neighborhoods like Pilsen, Chinatown, Boystown and Lincoln Park to join crowds of onlookers toting handmade signs, blaring music and encouraging all of the runners as they whiz by, or meet your runner at the reunite area of Grant Park starting at 9:30am. 

Celebrating Chicago culture through couture, Chicago Fashion Week brings runway shows, markets, educational programs and more—many of which are free to attend—throughout the city. The full gamut of programming is yet to be announced; stay updated via CFW's website. 

The inaugural Chicago Art Fair is bringing top galleries from across the globe to THE MART this fall. The four-day event, ideal for collectors, designers, buyers and art enthusiasts alike, will showcase contemporary and modern fine art paintings, sculptures, photography, mixed media and more.

Looking to learn a little more about wine? Head to Jonquil Park for the annual Lincoln Park Wine Fest, where sommeliers and brand ambassadors will coach you through a two-hour tasting session. A general admission ticket comes with a sample of 12 varietals of wine and a commemorative tasting glass. Spring for a VIP ticket for an expanded tasting that includes five additional specialty wine samples. Either way, you'll be able to watch live music performances while you sip. 

Returning to a two-acre plot of land just west of Goose Island, Jack's Pumpkin Pop-Up saves you a trip to the suburbs by bringing a huge corn maze, thousands of pumpkins, axe throwing, carnival games, food trucks, twinkling orange light displays and more fall fun to the city. A general admission ticket gets you access to the pop-up, but you can also opt for add-ons that let you take home a pumpkin, grab a drink at one of bars or go axe throwing.

International DJ Diplo pairs miles with music, and his touring run club is making its first stop in Chicago. The 5K run through Humboldt Park culminates with a live performance by the DJ himself. Runners can upgrade to the VIP Experience, which gets you access to a dedicated viewing area, exclusive sponsor activations, VIP entry and easy check-in on race day.

Check out galleries and artistic spaces around Wicker Park and Bucktown during this free monthly event on the first Friday of each month. Venues will keep their doors open until 8pm so guests can meet gallery owners and artists, and explore a range of local art. Participating spots include Graveface Chicago, Little Broken Things, Heaven Gallery, David Leonardis Gallery and more.

Wanna see some of the best Halloween costumes in the city? Head to Northalsted, where hundreds of people show off their creations at this spooky festival and procession. During the day, a street fest features food, drinks, live entertainment and more. At 7pm, you'll find drag queens, kids, parents and pets marching in the 30th annual Halsted Halloween Night Parade, which typically features impressive group costumes and dancers performing all the moves to Michael Jackson's "Thriller." Stick around afterwards for the costume contest awards ceremony.

Get in the holiday spirit at this annual ghoulish makeover of the Chicago Botanic Garden. The event brings together more than 1,000 real pumpkins—some weighing up to 150 pounds—which are LED-lit creations and staged along the garden's pathway, where other entertaining characters and activations await visitors. This year, a new 20-foot inflatable sculpture called "Monarch Skull" by artist Alyse Gamson joins the Garden's elaborate Halloween takeover. Seasonal snacks and drinks are available for purchase, in case all that wandering makes you hungry. 

The NYC vintage market visited by celebs like Brooke Shields, Molly Rogers and Law Roach is headed to Fulton Market for the first time. The inaugural two-day market is the first of two each year, with finds from esteemed vintage dealers from the New York City show like Closet Case Vintage, Elite Repeat, Molimo and many more.

Hosted at Stolen Saddle—one of Chicago's largest country bars—this annual Halloween-themed extravaganza features photo ops galore, plus an upstairs bar serving spooky cocktails like Freddy’s Tequila and Darcula's Blood. There’s no haunted house this go-around—but that doesn't mean Nightmare on Clark Street won't be serving up scares this Halloween season.

Experience the thrill of sumo wrestling up close at the traveling experience Sumo + Sushi's stop in Chicago. The event kicks off with an introduction to the history and rituals of sumo, followed by live exhibition matches. Guests can purchase a Sushi + Show ticket for an upgraded experience that includes a sushi bento box, miso soup and mochi, courtesy of a local sushi restaurant. Think you have what it takes to compete? Six guests per session can opt for the Get in the Ring experience and face off against wrestlers in front of the crowd. 

The team at Fulton Market restaurant Ever is hosting a 1980s-themed Halloween soiree across three spaces: After, The B-Side and The Canvas by Ever. A ticket to this spirited evening includes food and drinks, plus access to all three spaces throughout the evening. Each venue will transform into a different retro-inspired haunt, featuring horror film references, music and Michelin-level fare.

Take the little ones trick-or-treating in Lincoln Park for some Halloween fun this spooky season. Businesses along Lincoln Avenue from Diversey Parkway to Webster Avenue on Saturday; and along Clark Street from Armitage Avenue to Diversey Parkway, and on Diversey Parkway from Lakeview Avenue to Orchard Street on Sunday will hand out candy to trick-or-treaters, so come dressed in costume. There will also be a special Halloween celebration at Lincoln Common Plaza on Saturday with a DJ, face painting, a photo booth, a balloon artist and more.

The Second City is reviving its annual Halloween series for a third time with Travel Can Be Murder, a 90-minute, unscripted whodunit inspired by Murder on the Orient Express and Death on the Nile. Based on a single audience suggestion, performers build a live, on-stage mystery that the audience must solve before the final line. 

Explore Chicago's eerie past as you snake down the river aboard the First Lady Creepy Cruise. The 90-minute tour combines architectural history with stories of the city's shady past, from mob legends to ghost sightings, for a spooky evening on the water.

This annual (and free) arts-centric Halloween parade returns to Columbus Drive for an evening of colorful, family-friendly flair. Watch as participants from major cultural organizations, youth programs and aspiring artists march from Balbo Drive to Jackson Boulevard. Arts in the Park is bringing back its "Upside Down" parade in Washington Park on Halloween night, where attendees can walk through a route thronged by costumed performers and puppeteers. 

Join LondonHouse Chicago for a spooky evening of Halloween fun across two unique spaces: The stylish LH on 21 Lounge and the iconic LH Rooftop, each offering a festive carnival atmosphere with eerie surprises. Guests will enjoy a premium open bar from 9pm to 1am and live DJ entertainment all night. There will also be a costume contest at midnight. The winner will receive an overnight stay at LondonHouse and two tickets to the hotel's New Year’s Eve event.

Artists take over neighborhood shops during the annual West Town Art Walk, which showcases the creative talents of area residents and businesses. The festival celebrates all kinds of art, including visual, fashion, musical and culinary—choose your own adventure by customizing where you start your art walk, which can be launched at any of the fest's participating businesses. Need assistance walking? Flag down one of the art walk's free pedicabs for a ride. 

This annual fall street festival returns to Lincoln Square with more than 100 vendors for one apple-filled weekend. Shop autumnal goods at the festival's marketplace, munch on apple-infused fare from local restaurants, sip cider and apple-flavored beer, catch live music performances and bring the kids for seasonal activities.

Displaying a 25-story-tall video installation on the side of THE MART, ART on THE MART is the largest permanent digital art projection in the world, with programming that changes seasonally. ART on THE MART's array of 34 digital projectors show the creations after dusk every evening. Running for 30 minutes on Thursdays through Saturdays, it’s best viewed from the section of the Chicago Riverwalk between Wells Street and Franklin Street.

Celebrate wellness, art and health at the free one-day festival, Healing Arts Chicago Summit. Chicagoans are invited to participate in programming like artist-led workshops, sit in on panels focused on workforce development, and join yoga, dance, movement and journaling sessions. 

TEDxChicago is returning for another edition of inspiring talks this fall. The schedule of events and lineup of speakers have not yet been announced. Last year's programming included a talk with an astronomer at the University of Chicago and talks with doctors and philanthropists at Harris Theater for Music and Dance.

From model to battlefield correspondent—and with many other titles in between—Lee Miller was a complex figure, and this year, the Art Institute of Chicago is showcasing works from her career in an expansive exhibit titled Lee Miller: Fearless. The first comprehensive survey of Miller's photographs in more than 25 years, Lee Miller: Fearless will feature nearly 150 works and will explore her life and approach to creativity, both behind and in front of the camera.

Chicago Seadog offers a spooky ride down the river and lake this season with its Haunted Tours. The 75-minute tours, offered on Fridays, Saturdays and Sundays through October, are moderated by a costumed guide, who shares the eerie history of supernatural occurrences in Chicago. Guests (and their dogs!) are encouraged to come in costume and BYOB if they want to get boo-zy on board.

The Haunted House Party is back at the Shedd Aquarium, bringing together house music and Halloween for a spooky night to remember. Despite the event's name, there will be no scares here—the event's vibe is decidedly more "house party" than "haunted." Guests aged 21 and up are invited to come dressed in their finest costumes and dance the night away to sets by DJ Gent Hunt and DJ Heather.

Red Bull is bringing its Setlist experience to the U.S. for the first time for a one-night show at Radius. Headlined by Lil Yachty, Red Bull Setlist lets fans vote on elements of Lil Yachty's set, from the songs and performance style to surprise moments. Plus, in the weeks leading up to the show, Red Bull is giving local artists a chance to open for Lil Yachty by auditioning in a mobile recording studio.

Explore limited-edition comics, artist books, zines and art by more than 100 artists and independent publishers at Pretty Good Fest. The free fair features exhibitors, readings and other events, plus programming with special guests and acclaimed cartoonists Chris Ware, Michael DeForge and Tara Booth.

The Music Box Theater brings back its beloved annual Halloween tradition with five screenings of The Rocky Horror Picture Show. Each screening is paired with a shadowcast as actors perform in front of the screen during the film. It's a wonderfully weird tradition that's known to sell out.

If three hours in the theater wasn't enough Odyssey for you, then you're in luck. The National Hellenic Museum is celebrating the most iconic story of all time with a lineup of programming centered around Homer's epic, including the art exhibition The Odyssey Reimagined. Featuring works by 17 contemporary artists, the exhibit explores the current-day connections to the nearly 3,000-year-old story through paintings, photography, textiles, sound and more. 

This touring exhibition honoring one of the country's most significant sculptors of the 19th century stops at the Driehaus Museum. Known for major works like the Bethesda Fountain in New York City's Central Park, Stebbins' marble and bronze works are showcased in this career-spanning exhibition of sculptures, paintings, archival materials and more.

In addition to the regular Arts in the Dark parade on State Street, the arts organization LUMA8 is hosting a "reverse" parade—in which attendees pass through a stretch of costumed performance groups lining Russell Drive in Washington Park. Bonus: At the end of the route, attendees will get a complimentary candy bag and other goodies. Come wearing your best Halloween costume!

Nearly 20 years after their original Burnin' Up Tour, the Jonas Brothers are hitting rewind with The Burning Up Tour All Over Again, and they're stopping in Chicago. The brothers will headline the Allstate Arena in Rosemont for one night to play nostalgic hits like "Burnin' Up," "BB Good," "Hold On" and more.

Whether it's on a minibus or on foot, this tour takes you to the locations frequented by some of Chicago's most notorious gangsters and the places that have been haunted by their ghosts. With four tours offered daily, there's always an opportunity to take a step back in time to learn about figures like Al Capone and Chicago's haunted history.

Six bars from Mexico City are popping up in River North this Halloween for Three Dots and a Dash's Terror in the Tropics: Midnight in Mexico celebration. The bars will each be pouring signature cocktails all night at Salon 61, where guests (who are encouraged to come in their best costumes) can enjoy DJ sets and the five drinks included with a GA ticket.

Chicago's most adorable Halloween party happens every year at the MCA Sculpture Garden, where local dog and cat owners bring their costumed pets for a parade around the premises. The best-dressed furry friend—chosen by Alderman Brian Hopkins and Streeterville resident Maureen Schulman—will receive prizes. Donations support the dogs, cats, kittens and puppies residing at PAWS Chicago.

Sanctum returns for another weekend of dark music, dancing and community at Thalia Hall and its piano lounge, Tack Room, this Halloweekend. Sanctum prides itself on standing head and shoulders above other music festivals, bringing in extra sound support from Big Audio, decking the room with curated decor and offering an “ALL VIP” ticketing concept that grants all attendees the same level of access. This year's lineup includes A Split Second, Buzz Kill, Pink Stiletto, Grave Love and more, plus a VHS Dungeon Room, photo booths, vendors and more.

Round up your family for a wild, multi-week Halloween festival at Brookfield Zoo. Decorate a pumpkin, take a spin on the decked-out carousel or pose for photos amongst giant inflatables and wooden cut-outs of Halloween characters. The not-too-spooky event also treats some of the zoo's animals—including gorillas, goats and lemurs—to pumpkins that they can play with, nibble on and smash. 

Make your Halloween a little BOO-zier with the Ravenswood Costume Crawl, which invites costumed attendees to stroll along a route stocked with local desserts, snacks and drinks samples on Montrose and Ravenswood Avenues. After the crawl, head to Koval Distillery for an afterparty with a costume contest, tarot readings and more.

You don't need alcohol to get in on the Oktoberfest fun. Head to Mocktoberfest at Palmhouse in suburban Evanston for a zero-proof celebration, with non-alcoholic drinks, German-themed food, live music and an artisan marketplace. Tickets include unlimited beverage samples, plus free chair massages and tarot readings, table games, a stein-holding contest and more.

What's better than dressing up on Halloween? Dressing up your pups, of course! This spooky season, the Howl-O-Ween Canine Cruise aboard First Lady is back for a limited-time, 90-minute lake and river cruise. Costumed dogs (and humans!) are invited to board the cruise to enjoy a narrated journey complete with pumpkin-flavored dog treats and a canine costume contest. The winners will be entered to receive a grand prize of a $1,000 made by First Lady in the winner's name to a canine organization.

Guitar for Guaraldi is an annual free concert celebrating the work of Vince Guaraldi—the American jazz pianist best known for scoring the television adaptations of the Peanuts comic strip. Throughout the night, the Mich Shirley Trio will perform true-to-form guitar arrangements featured in It's the Great Pumpkin, Charlie Brown. 

North Center's Timber Lanes Bowling Alley is hosting a Big Lebowski costume contest (with prizes!) and concert this spooky season. Tickets include bowling and live performances by the bands The Bart Attacks and Rochambeau, and solo acts Marty Bennett and Damon Groen.

The masterminds behind the irreverent long-running comedy show Drunk Shakespeare are unleashing their latest monster mash-up, Drunk Dracula, on the city during the month of October. The premise is simple, but no less hilarious: Dracula gets drunk, unsuspecting citizens fight for survival and Bram Stoker’s vampire classic gets a boozy makeover that’s equal parts unhinged and fun.

Looking for a great way to start your weekend? Lululemon ambassadors and local run leaders host a free weekly run club every Saturday morning. Runs start at the brand's Rush Street store in the Gold Coast, before heading down the Lakefront Trail and back to the store for post-run snacks. The run route is 3 miles, but multiple distances and durations are offered as well. Dogs, strollers and runners of all experience levels are welcome—just be sure to sign up in advance.

Spooky season will get a bit boozier this year thanks to this horror-themed cocktail pop-up at the Albion Manor, where Halloween lovers can sip expertly mixed cocktails amid metal music and goth decor. Drinks are imbued with playful touches and include choices like Abyssa’s Obsession made with pumpkin-infused rums, and the tequila-based Bone Temple. Want to recreate the creepy vibe at home? Several of the drinks are served in Halloween glassware that’s available for purchase onsite.  

Take a spooky step back in time to the age of Oak Brook's early settlers at the annual Cemetery Walk through Bronswood Cemetery. Guides will lead small groups down a half-mile path illuminated by lanterns as they share the tales of the community's pioneers. The one-hour walk includes a rest at the halfway point where guests can take a break and enjoy complimentary refreshments.

Chicago's largest Oktoberfest celebration is returning to the heart of Fulton Market. Located just behind Restaurant Row at 171 N. Peoria St., this lively six-week German fest is pouring Hofbräu München beer imported directly from Germany. Guests can also expect Bavarian pretzels, brats, live German music, carnival games and more. 

Dovetail Brewery and Begyle Brewing Company are teaming up once again for their annual fall bash in celebration of Oktoberfest. Taking place outside in the shared lot between the breweries, Oktoberfestiversary features special beer tappings (alongside favorites from Dovetail and Begyle), live music and delicious bites from food trucks, including Bad Johnny's, El Zorro Tacos and Soul & Smoke. A $5 suggested donation benefits local food pantry The Friendship Center.

Explore notable Impressionist Mary Cassatt's works in the first exhibit in more than 25 years dedicated solely to the American artist at the Art Institute. Known for her works depicting mothers with children and intimate caretaking scenes, Cassatt was the only American to join the French Impressionists. After Impressionism showcases paintings, pastels and prints from the time in her career when she began to take her art in a new direction.

A Gen Z version of Grease takes the stage at the Apollo Theater this season. Vape! The Grease Parody is an Off-Broadway spoof of the iconic 1978 musical, complete with playful takes on the original storylines, modern references and, yes, vapes instead of cigarettes.

Celebrate Oktoberfest over the course of three weekends at The Northman Beer & Cider Garden, which is bringing a host of festivities to its Riverwalk digs this September and early October. Expect giant pretzels and German sausages, beer steins and polka music, and scenic waterfront views with a European vibe.

Lincoln Park exhibition space Wrightwood 659 presents an engaging show that features the works of three trailblazing women: Yayoi Kusama, Niki de Saint Phalle and Mary Bauermeister. Inner Worlds showcases large-scale works, mixed-media works, sculptures and more by the artists, who are acclaimed for their approaches to perception and embodiment. Highlights of the exhibit are two of the late Kusama's Infinity Mirror Rooms.

This exhibition poses a devastatingly powerful question: What if Emmett Till had not been brutally lynched in Mississippi in 1955? Through photography, the exhibition imagines an alternate history in which Till lived—moving from images inspired by the last meal his mother packed before his trip south to meditations on the life he might have experienced, from the rise of the Chicago Bulls to the ongoing fight for civil rights.

This weekly “live magazine” is a cavalcade of culture, politics and wit featuring journalists, actors, comedians and musicians offering idiosyncratic reports on the news of the day. Head to Uptown’s iconic Green Mill for drinks, hot takes and laughs; the longstanding Saturday afternoon edition tends to run about two and a half hours.

For more than 30 years, the Neo-Futurists have been delighting late-night crowds with performances that pack 30 miniature plays into a 60-minute show. The company's signature show is more unpredictable than ever these days, with a handful of compact new plays premiering every week. Within the span of 10 minutes, you may be treated to a poignant monologue about everyday life or an irreverent diatribe delivered by a pantsless member of the cast—all inspired by the experiences of the performers on stage. Always changing and evolving, it's the rare show that truly offers something different everytime you show up to see it.

Whether you’re parenting a pint-sized Pokémon devotee or a nostalgic millennial still clinging to a holographic Charizard card for its “possible resale value” (guilty), the Pokémon Fossil Museum is designed to surprise and delight. Having made its U.S. debut at the Field Museum in May, the immersive exhibition invites visitors to compare Fossil Pokémon like Tyrantrum and Archeops with real-world fossils—including SUE the T. rex. Expect Pokémon models, real fossil-excavation tools and immersive activations throughout.

Explore music from around the globe during this annual festival, now in its 24th year, which brings a wide array of performers to venues across the city for free musical performances. Experience sounds and subgenres from regions like Brazil, South Korea, Senegal and more. For a full list of performances, visit the festival's website. 

Explore a host of galleries and programming at this monthly event that showcases West Town’s dynamic arts community. On the first Friday of every month, galleries and arts-based businesses stay open until 8pm.

Originally established in the late 1800s, the Maxwell Street Market brought vendors, musicians and cooks to an open-air flea market where shoppers could find just about anything they wanted. The market introduced the Maxwell Street Polish sausage, provided a venue for rising Chicago blues musicians and was immortalized in a scene in The Blues Brothers. These days, the market sets up on Maxwell Street, between South Halsted Street and South Union Avenue on Sundays, where visitors will find vendors hawking their wares, an abundance of delicious Mexican food and occasional performances by local bands and dance troupes. 

Ready to explore Chicago's amazing architecture while floating on the river? The Chicago Architecture Center River Cruise takes place aboard a First Lady boat, transporting guests on a 90-minute tour that traverses three branches of the Chicago River and explores the stories behind more than 50 buildings that make up the city's iconic skyline.

Each Sunday, a small horde of farmers, vendors and shoppers descends on Wicker Park for the neighborhood's farmers market, which features fresh regional goods. The Wicker Park Farmers Market runs from 8am to 2pm on Sundays from May 3 through October 25. On Thursdays through October 29, check out the market at Walsh Park from 4pm to 8pm.

The Whistler’s monthly lit series pops up on the second Wednesday of every month, bringing an evening of readings, workshopping and discussion to the Logan Square cocktail bar. Each show is followed by an installment of the Relax Attack Jazz Series, a free event with a constantly rotating bill.

Every Wednesday, the Old Town School of Folk Music hosts a showcase of world music and dance. Featuring both local and touring talent, you're sure to hear something new and exciting at this long-running series. Before the show, be sure to peruse the Old Town School of Folk Music Store, where you can rent instruments, learn about lessons and peruse a wide selection of books.

Find your flow with the whole family in the cozy confines of the Peggy Notebaert Nature Museum at a Brain to Belly Kids Yoga session! This creative class flows through several fun poses, each one complementing the month's children's story. Children (ages two to eight) and their grown-ups will enjoy moving, breathing and connecting together while bringing the story's plot to life. Bonus: Your ticket includes full access to all museum exhibits, so stick around after class!

Escape the planet with exhibits about the first lunar missions, the solar system and more, plus immersive shows in the dome theater. Stationed just a stone's throw away from the Adler, the Doane Observatory is also home to the largest public telescope in the area and gathers 7,000 times more light than the human eye. Every Wednesday, the Adler stays open late from 4pm-10pm so that folks can visit after work or school. And best of all, admission is free on those nights for Illinois residents.

Just when you thought the state's largest mall couldn't surprise you anymore, Woodfield Mall announces WONDRA, a sprawling new immersive experience. Inside, you’ll wander through enchanted meadows that respond to the sound of your voice, stumble across bioluminescent landscapes and drift into crystal caves and celestial gardens that blur the line between digital spectacle and raw wonder. Every corner is crafted to ignite curiosity and inspire a sense of awe we, whether you’re a kid seeing it all for the first time or an adult who forgot what it feels like to play.

As the Driehaus Museum’s first artist-in-residence, Brendan Fernandes will transform the Murphy Auditorium into a dynamic site for sculpture, movement and sound. Inspired by the Judson Dance Theater, Fernandes’ Scores for the Murphy Auditorium will unfold as an episodic residency throughout 2026, with performances and public programs announced over time.

Head to 360 Chicago on Saturdays for yoga with a killer view. Instructor Britta Eumann will lead an hour-long class on the 94th floor of 875 North Michigan Avenue (formerly the John Hancock Center) that’s suitable for all ages and skill levels—you just need to bring your own mat and arrived properly dressed. Registration is $55 and includes a cocktail or coffee, plus admission to the observation deck so you can stick around and snap some photos after you're done striking poses on the mat.

"Flyway City: Architecture for a Flourishing Ecosystem," designed by Studio Gang and led by world-renowned architect Jeanne Gang, explores solutions to prevent the estimated one billion annual bird-glass collisions in the U.S. Through a variety of architectural models, interactive media and local artifacts, the exhibition demonstrates how urban design can coexist harmoniously with nature. 

This immersive exhibition recreates the Secret Annex where Anne Frank, her family and four others hid during the Nazi occupation of the Netherlands. Chicago is only the second U.S. city—and the first in the Midwest—to host the experience, which includes rarely seen artifacts from Frank’s life. Visitors can walk through the reconstructed hiding place while learning about Anne’s childhood, the rise of Nazi Germany and the Frank family’s years in Amsterdam. The exhibition offers a powerful look at the risks, courage and daily realities of those who lived in hiding.

Intuit Art Museum joins the national Handwork 2026 celebration with an exhibition investigating Henry Darger’s relationship to traditional American paper crafts. Drawing on research by art historian Dr. Mary Trent, the exhibition demonstrates how Darger adapted common practices—such as making paper dolls and scrapbooks—into a complex, mixed-media narrative style. By showcasing Darger’s source materials alongside his final works, the exhibition highlights how he reclaimed these institutionalized hobbies to express the interior lives and struggles of the marginalized.

You’ve probably seen a Shakespeare play before, but never like this. Five professional actors come together for each performance of Drunk Shakespeare. The twist? One of them has had five shots before the show and is trying to stay on track while the other four actors do their best to hold the performance together.

Located inside The Den, a 1920s greystone-turned-hotel in Lakeview, the Blind Wolf Speakeasy is an intimate, approachable bar, event venue and home to a free weekly comedy show. Blind Wolf Comedy hosts a rotating roster of Chicago comics each Wednesday at 8pm, as well as open mic nights on Thursdays at 7:30pm. There's no cost to attend, but you can reserve a seat through their Instagram page.