Chicago events this weekend
Every curated Chicago event we're tracking right now — with photos, dates and neighbourhoods, each linking straight to the event's own page. Below it, an easier way to actually decide: HeyWeekend gives you and your person the same small set of nights, you each swipe, and anything you both like is settled.
Starting soon
The next few nights on the calendar.
Theatre & performance
Now through Sun, Nov 8Broadway Playhouse at Water Tower Place; 175 E. Chestnut St .Chicago, IL 60611
Fairs & festivals
Now through Sun, Nov 1Lincoln Park Zoo · Lincoln ParkFree
Galleries & art
Now through Sat, Oct 31Navy Pier, 600 E Grand Ave, Chicago, IL 60611, United States
One-of-a-kind nights
Now through Sat, Oct 31Navy Pier · Streeterville
Markets & food
Fri, Oct 23Hubbard Inn
All events
When
Where
Type
Showing 110 of 110 events
- Jekyll& Hyde(opens the event website in a new tab)
Now through Sun, Nov 8Broadway Playhouse at Water Tower Place; 175 E. Chestnut St .Chicago, IL 60611
Kokandy Productions’ critically acclaimed revival of the 10-time 2025 Jeff Award–nominated musical JEKYLL & HYDE will make its Broadway In Chicago debut at the Broadway Playhouse at…
The 37th Annual Rhinoceros Theater Festival Returns September 20 – October 26 at Four Chicago Venues(opens the event website in a new tab)Now through Mon, Oct 26Facility Theatre; 1138 N California Ave, Chicago, IL, 60622
Curious Theatre Branch, with co-producers Chicago Danztheater Ensemble, Chicago Dramatists and Labyrinth Club, are pleased to announce the 37th annual Rhinoceros Theater Festival, September 20…
- Fall Fest at Lincoln Park Zoo(opens the event website in a new tab)
Now through Sun, Nov 1Lincoln Park Zoo · Lincoln ParkFree
Chicago’s favorite free and family-friendly festival is back at Lincoln Park Zoo for another season of harvest-time fun! From September through October, stop by the…
“Dead Girl’s Quinceañera” – Tickets On Sale Fri Aug 7!(opens the event website in a new tab)Now through Sun, Nov 1Goodman Owen Theatre
TICKETS ON SALE AUG 7 September 26-November 1 By Phanésia Pharel Directed by Melia Bensussen Detective skills: unverified. Determination: unmatched. FACT: Maria was last seen at her…
- INCREDIBLE INSECTS: Interactive Live Bug Exhibit(opens the event website in a new tab)
Now through Sat, Oct 31Navy Pier, 600 E Grand Ave, Chicago, IL 60611, United States
This Halloween season, join us for the third year of Incredible Insects at The Butterfly House at Navy Pier: an interactive exhibit featuring wacky and…
Oil Lamp Theater Presents “Dial M for Murder”(opens the event website in a new tab)Now through Sun, Nov 1Oil Lamp Theater
Oil Lamp Theater is proud to announce the cast and creative team for its next production, Dial M for Murder, October 2 – November 1,…
BOO! at the Zoo(opens the event website in a new tab)Now through Sun, Oct 25Brookfield Zoo Chicago; 3300 Golf Rd
Get ready for a boo-tiful day of Halloween fun at BOO! at the Zoo, Brookfield Zoo Chicago's family-friendly fall tradition! Enjoy festive décor, not-so-scary surprises,…
Tin Drum Theatre Company Presents the Chicago Premiere, “A Dark Wood”(opens the event website in a new tab)Now through Sun, Nov 1Greenhouse Theater Center · Lincoln Park
Tin Drum Theatre Company announces the Chicago premiere of A Dark Wood, October 15 – November 1, written by Eric Coble and directed by Steve…
- Slightly Spooky October at Navy Pier(opens the event website in a new tab)
Now through Sat, Oct 31Navy Pier · Streeterville
Join us for free movies at Navy Pier in Crystal Gardens on Saturdays, October 17 and 24, plus trick-or-treating throughout the Pier on Halloween, October…
Fright at the Field(opens the event website in a new tab)Now through Sun, Nov 1The Field Museum; 1400 S Lake Shore Dr,
Spooky season has arrived at the Field Museum! Join us for Fright at the Field, a Halloween experience featuring the return of Underground MISAdventure, and…
The Book Of Mormon(opens the event website in a new tab)Fri, Oct 23Cadillac Palace Theatre · Loop
The Book of Mormon is returning to Chicago for a limited limited engagement from Friday, October 23 through Sunday, November 1, 2026. From the creators…
17851980(opens the event website in a new tab)Fri, Oct 23The Salt Shed
[](https://do312.com/events/17851980) [The Salt Shed](https://do312.com/venues/the-salt-shed)
- judy-collins(opens the event website in a new tab)
Fri, Oct 23Old Town School of Folk Music · Old Town School of Folk Music
[Gary and Laura Maurer Concert Hall Presents](https://do312.com/events/2026/10/23/judy-collins-tickets) [Old Town School of Folk Music](https://do312.com/venues/old-town-school-of-folk-music)
- lissie(opens the event website in a new tab)
Fri, Oct 23Robert's Westside
[Presented by Robert's Westside.](https://do312.com/events/2026/10/23/lissie-tickets) [Robert's Westside](https://do312.com/venues/robert-s-westside)
- Chicago Wine Fest at Hubbard Inn – Tastings Included(opens the event website in a new tab)
Fri, Oct 23Hubbard Inn
Tix include 15 tastings, giveaways & more! There will be a variety of wines to try at this one of a kind venue! Wine not…
Travel Can Be Murder(opens the event website in a new tab)Fri, Oct 23Second City · Lincoln Park
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.
- Black Lagoon(opens the event website in a new tab)
Fri, Oct 23Albion Manor · Lincoln Park
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.
Inner Worlds: Visions from the Hirshhorn Collection(opens the event website in a new tab)Fri, Oct 23Wrightwood 659 · Lincoln Park
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.
Drunk Dracula(opens the event website in a new tab)Fri, Oct 23Loop
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.
Chicago Seadog Haunted River Tour(opens the event website in a new tab)Fri, Oct 23Chicago Seadog · Streeterville
Chicago Seadog, part of City Cruises Chicago, 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 Odyssey Reimagined(opens the event website in a new tab)Fri, Oct 23National Hellenic Museum · Greektown
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.
ART on THE MART(opens the event website in a new tab)Fri, Oct 23THE MART / Chicago Riverwalk
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.
Night of 1,000 Jack-o’-Lanterns(opens the event website in a new tab)Fri, Oct 23Chicago Botanic Garden
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.
Boo! at the Zoo(opens the event website in a new tab)Fri, Oct 23Brookfield Zoo · Brookfield
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.
WONDRA(opens the event website in a new tab)Fri, Oct 23Woodfield Mall
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.
Mary Cassatt: After Impressionism(opens the event website in a new tab)Fri, Oct 23Art Institute of Chicago · Grant Park
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.
Cutting and Pasting a World: The Paper Craft of Henry Darger(opens the event website in a new tab)Fri, Oct 23Intuit Art Museum · River West/West Town
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.
DETROIT ’67(opens the event website in a new tab)Fri, Oct 23eta Creative Arts Foundation
Detroit ’67 A Play by Dominique Morisseau Directed by Aaron Reese Boseman Running through November 1, 2026 ★★★★ “HIGHLY RECOMMENDED. THE CAST IS FIRE!” –Bonnie…
Howl-O-Ween Canine Cruise(opens the event website in a new tab)Fri, Oct 23First Lady · Loop
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.
Nightmare on Clark Street(opens the event website in a new tab)Fri, Oct 23Stolen Saddle · Wrigleyville
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.
Old Joliet Prison Flashlight Tour(opens the event website in a new tab)Fri, Oct 23Old Joliet Prison · Joliet
Explore the historic Old Joliet Prison under the cover of the night this spooky season. In the Flashlight Tour, guests will wander through the facility with just a flashlight as they learn about the prison's operations and dark history.
Jack's Pumpkin Pop-Up(opens the event website in a new tab)Fri, Oct 23River West/West Town
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.
Oktoberfest Nation(opens the event website in a new tab)Fri, Oct 23West Loop
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.
Vape! The Grease Parody(opens the event website in a new tab)Fri, Oct 23Apollo Theater · Sheffield & DePaul
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.
If Emmett Till Lived: Freedom on American Ground(opens the event website in a new tab)Fri, Oct 23Loop
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.
Gangsters & Ghosts Tour(opens the event website in a new tab)Fri, Oct 23
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.
Emma Stebbins: Carving Out History(opens the event website in a new tab)Fri, Oct 23Driehaus Museum · River North
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.
A Tale of Today Presents Brendan Fernandes: In the Round(opens the event website in a new tab)Fri, Oct 23Murphy Auditorium (Driehaus Museum) · River North
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.
Drunk Shakespeare Chicago(opens the event website in a new tab)Fri, Oct 23Loop
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.
- Jack O' Lantern World (Oct. 23-25):(opens the event website in a new tab)
Fri, Oct 23Paulus Park · Lake Zurich
Families can explore a glowing Halloween trail at Paulus Park in Lake Zurich, featuring illuminated pumpkins, creative carvings and festive displays. Enjoy a 45-minute outdoor walk filled with colorful Halloween creations.
The Infinite Wrench(opens the event website in a new tab)Fri, Oct 23Uptown
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.
Anne Frank The Exhibition(opens the event website in a new tab)Fri, Oct 23Hyde Park
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. Admission is free on Friday, June 12 in honor of what would have been Anne's 97th birthday. Guests can also enjoy the exhibit for free with the purchase of a general admission ticket for the rest of the weekend.
Zoo Brews: Howls and Growls(opens the event website in a new tab)Fri, Oct 23Lincoln Park Zoo · Lincoln Park
Come for the brews, stay for the boos! Zoo Brews: Howls and Growls is an adults-only Halloween party at Lincoln Park Zoo that lets you…
Lee Miller: Fearless(opens the event website in a new tab)Fri, Oct 23Art Institute of Chicago · Grant Park
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 Architecture Center River Cruise aboard First Lady(opens the event website in a new tab)Fri, Oct 23First Lady boat (Chicago Architecture Center River Cruise) · Loop
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.
Flyway City: Architecture for a Flourishing Ecosystem(opens the event website in a new tab)Fri, Oct 23Loop
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.
Creepy Cruise(opens the event website in a new tab)Fri, Oct 23First Lady · Loop
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.
62nd Chicago International Film Festival(opens the event website in a new tab)Fri, Oct 23
As the longest-running competitive film festival in North America, The Chicago International Film Festival brings more than 150 films from around the world to Chicago.…
Pokémon Fossil Museum(opens the event website in a new tab)Fri, Oct 23Field Museum · Museum Campus
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. Making its U.S. debut at the Field Museum in spring 2026, the international 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 soundscapes throughout.
- 420 Frankenstein(opens the event website in a new tab)
Sat, Oct 24de Maat Theatre at Second City
The creator of 420 Shakespeare is bringing Mary Shelley’s monster to life… with a little help from Mary Jane. On a dark and stormy night,…
Pretty Good Fest(opens the event website in a new tab)Sat, Oct 24LoopFree
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.
Día de los Muertos Xicágo(opens the event website in a new tab)Sat, Oct 24Harrison Park · Pilsen
In Pilsen, the National Museum of Mexican Art hosts this annual community gathering to honor Day of the Dead. Enjoy live music and performances, art activities, and a stunning illuminated ofrenda.
Spooktacular: Lincoln Avenue(opens the event website in a new tab)Sat, Oct 24Lincoln Avenue, between Wrightwood and Webster · Lincoln Park
Get ready for two days of trick-or-treating fun in Lincoln Park! Spooktacular returns with a weekend of Halloween festivities for the whole family. Dress up…
I am the Wind(opens the event website in a new tab)Sat, Oct 24Theatre Y
Two lifelong friends sail into open water: one edging closer to the pull of oblivion, the other with a question neither can escape. Nobel laureate…
Red Bull Setlist(opens the event website in a new tab)Sat, Oct 24Lower West Side
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.
Manhattan Vintage(opens the event website in a new tab)Sat, Oct 24River West/West Town
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.
Chicago Bulls vs. Washington Wizards(opens the event website in a new tab)Sat, Oct 24United Center; 1901 W Madison St, · West Loop
Come cheer on the Bulls!
Chicago Fall Market(opens the event website in a new tab)Sat, Oct 24Artifact Events; 4325 N Ravenswood Ave
Markets for Makers is coming to Chicago on October 24 + 25 at Artifact Events (4325 N Ravenswood Ave, Chicago, IL 60613). Come shop 90+…
Howl-O-Ween Canine Cruise(opens the event website in a new tab)Sat, Oct 24Chicago’s First Lady Cruises; 112 E Wacker Drive
Where are the pet parents who count down to dressing up their dog every Halloween? This one’s for you! Our 2026 Howl-O-Ween Canine Cruise is…
The Séance: Live (and dead) in Chicago(opens the event website in a new tab)Sat, Oct 24Stars and Garters Theater; 3914 N Clark St
We play with the dead. The Séance returns to Chicago's Stars & Garters for Saturday nights this fall. Recreating the atmosphere and techniques of 19th-century…
Yes, Chef! Chicago: A Bear-Inspired Food Tour(opens the event website in a new tab)Sat, Oct 24Ground Up Coffee & Bites; 363 W Erie St,
This is the ORIGINAL Chicago food tour that takes you to the restaurants featured on the TV phenomenon, The Bear. We'll take you to the actual…
Arts in the Dark(opens the event website in a new tab)Sat, Oct 24Free
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.
Tedeschi Trucks Band – Future Soul 2026 Tour(opens the event website in a new tab)Sat, Oct 24The Chicago Theatre · Loop
Award-winning blues-rock powerhouse The Tedeschi Trucks Band will conclude their “Future Soul 2026 Tour” with a four-night stand in Chicago in October 2026.
- Halloweensteen 2026 – Chicago, IL(opens the event website in a new tab)
Sat, Oct 24Park West
The popular annual rock celebration Halloweensteen is returning to Chicago on Saturday, October 24, 2026. Hosted by South Side native singer-songwriter Michael McDermott, this festive…
Pandemonium, Please Hold(opens the event website in a new tab)Sat, Oct 24The Second City · Old Town
The Second City’s 114th Mainstage Revue Pandemonium, Please Hold is a loud, fast, and gloriously unhinged night of comedic mayhem. The Second City’s six-person cast…
- Lupillo Rivera – 90’s CORRIDOS TOUR(opens the event website in a new tab)
Sat, Oct 24Rosemont Theatre
Lupillo Rivera is bringing his 90’s CORRIDOS TOUR to the Rosemont Theatre on Saturday, October 24, 2026. This concert features a nostalgic lineup of regional…
“Hollywood Hit” at Dinner Detective Chicago(opens the event website in a new tab)Sat, Oct 24Courtyard by Marriott Chicago Downtown Magnificent Mile
The Dinner Detective is an interactive comedic true crime dinner theatre experience based on real cold cases. Feast on dinner, but beware… the killer is…
- Zar the Star at The Comedy Bar(opens the event website in a new tab)
Sat, Oct 24The Comedy Bar · River North
2-Item Minimum Per Guest First Come, First Served Seating No Outside Food or Beverage Valid ID Required at Entry Zar the Star is a New…
- Saturday Night Sketch(opens the event website in a new tab)
Sat, Oct 24iO Theater · Lincoln Park
Saturday Night Sketch brings Chicago’s best sketch comedy ensembles to the stage for a high-octane evening. From sharp political satire to mind melting absurdity, come…
- Main Character Syndrome(opens the event website in a new tab)
Sat, Oct 24iO Theater · Lincoln Park
Main Character Syndrome is a solo character showcase by Chicago’s funniest improvisers presenting original SNL-audition ready character sketches. From Tim Robinson to Cecily Strong, iO…
- Standup Throw Down: Millennials vs Gen X(opens the event website in a new tab)
Sat, Oct 24The Second City · Old Town
Millennials take on Generation X in a live stand-up comedy battle – and the audience decides who wins. Hosted by Chicago comedian Todd Glover, Standup…
- Thee Phantom and The Illharmonic Orchestra(opens the event website in a new tab)
Sat, Oct 24The Riveria Theater · Uptown
Thee Phantom and The Illharmonic Orchestra will perform live at the Riviera Theatre in Chicago, Illinois, on October 24, 2026. Led by pioneering hip-hop maestro…
University Symphony Orchestra: Annual Halloween Concerts(opens the event website in a new tab)Sat, Oct 24Mandel Hall, University of Chicago
Pictures of the Imagination Colorful, exuberant, and sometimes scary musical pictures by Franz Liszt, Anatol Liadov, and George Whitefield Chadwick spur the imagination – and…
- Blondshell – Scaring Strangers Tour(opens the event website in a new tab)
Sat, Oct 24The Vic Theatre
Blondshell is scheduled to perform live in Chicago, Illinois on Saturday, October 24, 2026, as part of her newly announced “Scaring Strangers Tour”. Supporting Act:…
- Don Giovanni(opens the event website in a new tab)
Sat, Oct 24Lyric Opera of Chicago · Loop
The path to damnation never sounded so sweet The 2026/27 Season kicks off with a thrilling fable of deceit and retribution. Sharp humor, high drama,…
Sleeping Beauty & Dvořák Cello Concerto(opens the event website in a new tab)Sat, Oct 24Loop
The crown jewel of cello repertoire, Dvořák’s heroic and soulful Cello Concerto marks the return of Jian Wang, a soloist with a lustrous sound and…
Sugar Plum Fairy, P.I.(opens the event website in a new tab)Sat, Oct 24Lifeline Theatre · Rogers Park
Step into the sugary, shadowy world of Sugar Plum Fairy, P.I., a fairytale noir mystery filled with crime and double crosses! During the dark days…
Beverly Theatre Guild presents “Rodgers & Hammerstein’s Cinderella”(opens the event website in a new tab)Sat, Oct 24Baer Theater at Morgan Park Academy · Beverly
64th season opener, Cinderella. This classic rags-to-riches fairy tale with the world’s favorite princess is scheduled to be performed on October 23rd , 24th ,…
El Evangelio Jornalero – Destinos: 9th Chicago International Latino Theater Festival(opens the event website in a new tab)Sat, Oct 24St. Agustine’s College
This production is produced by Repertorio Latino TC and Colectivo El Pozo, written by Raúl Dorantes and directed by Joaquín Catana and Roma Díaz. El…
Adirondack Chair Circle(opens the event website in a new tab)Sat, Oct 24Steppenwolf Theatre Company · Lincoln Park
A gaggle of suburban moms, armed with pickleball paddles and hard kombucha, are ready to take on the school board in the fight of their…
Topdog/Underdog(opens the event website in a new tab)Sat, Oct 24Steppenwolf Theatre Company · Lincoln Park
“Take thuh cards and show me whatcha got!” Brothers Lincoln and Booth, named in jest, are two Black men living in America just trying to…
Jekyll& Hyde(opens the event website in a new tab)Sat, Oct 24Broadway Playhouse at Water Tower Place
Kokandy Productions’ critically acclaimed revival of the 10-time 2025 Jeff Award–nominated musical JEKYLL & HYDE will make its Broadway In Chicago debut at the Broadway Playhouse at…
Vampire Playlist – Destinos: 9th Chicago International Latino Theater Festival(opens the event website in a new tab)Sat, Oct 24El Schomburg
Vampire playlist by Concrete Content. Written by Xitlali Celeste, Angelica Davila, Pedro Arturo Jimenez, Luis Antonio Mora, Cielo Santiago Muñoz, Amelia Roque, Dani Suarez, Erik Ventura,…
America@250 – Now is the Time: Artists Go to Work(opens the event website in a new tab)Sat, Oct 24Court Theatre · Hyde Park
On July 4, 2026, America turned 250 years old. To reckon with the 250th anniversary of the Declaration of Independence is to reckon with freedom…
The Haunted Museum(opens the event website in a new tab)Sat, Oct 24Institute for the Study of Ancient Cultures
Do you dare enter the Haunted Museum? Guided demon hunts, spooky stories, creepy crafts, mummification demonstrations, and more! Dress up in your costume and experience…
Best of Second City(opens the event website in a new tab)Sat, Oct 24The Second City · Old Town
Find out for yourself why The Second City has been the first name in laughter for over sixty years! From the stages that launched the…
- The Best of IO(opens the event website in a new tab)
Sat, Oct 24iO Theater · Lincoln Park
Celebrate 45 years of improvisational excellence with the Best of iO Improv. This show brings together two teams of our very best improvisers, each delivering…
- The Wrecks – Finally : OUTSIDE Tour(opens the event website in a new tab)
Sat, Oct 24House of Blues · River North
Alternative rock band The Wrecks will bring their national fall headline run, the “Finally : OUTSIDE Tour,” to the House of Blues Chicago on Saturday,…
Holy Ghost Bingo: God, Goblins, & Games!(opens the event website in a new tab)Sun, Oct 25Stars & Garters Theater
Holy Ghost Bingo: God, Goblins, & Games is a Halloween-themed interactive comedy play written by Vicki Quade, one of the authors of the hit comedy,…
Marquee: Musical Improv(opens the event website in a new tab)Sun, Oct 25iO Theater · Lincoln Park
Musical theatre and improv collide as Marquee presents you with an hour of fully improvised musical comedy, spontaneously creating entire scenes, songs, and stories based…
Tartuffe(opens the event website in a new tab)Sun, Oct 251020 W Sheridan Road Chicago, IL 60660
Moliere’s Tartuffe is a five-act comedy satirizing religious hypocrisy, where the charlatan Tartuffe frauds the gullible Orgon by faking piety, seizing control of his home,…
T A K E | Visceral Dance Chicago(opens the event website in a new tab)Sun, Oct 25The Space at Rockwell
An immersive work set to an electronic recorded score mixed with live music, takes the audience “on a journey from darkness to light” TAKE is…
The Longest Johns Live In Concert(opens the event website in a new tab)Sun, Oct 25The Vic Theatre
The Longest Johns are performing live in Chicago on Sunday, October 25, 2026, at The Vic Theatre. The English folk band, famous for spearheading the…
Remy Bumppo Theatre Company Presents “Mud Row”(opens the event website in a new tab)Sun, Oct 25Theater Wit · Lakeview
Remy Bumppo Theatre Company is pleased to announce the cast, creative and production teams for the first production in its 2026 – 2027 season, Mud…
Matt Rife Live In Chicago – Stay Golden 2025-26 World Tour(opens the event website in a new tab)Sun, Oct 25United Center · West Loop
Comedian Matt Rife will perform live at Chicago’s United Center on Oct. 25, 2026.
Deep Schwa(opens the event website in a new tab)Sun, Oct 25iO Theater · Lincoln Park
Chicago’s longest-running Harold team returns to iO to bring their unique blend of chaos and creativity to iO’s signature form The Harold melding games, songs, and scenes…
Sleeping With Sirens – An Ending In Itself Tour(opens the event website in a new tab)Sun, Oct 25The Salt Shed
Alternative rock band Sleeping With Sirens will bring their headline An Ending In Itself Tour to Chicago on Sunday, October 25, 2026. The newly announced…
Vladimir(opens the event website in a new tab)Sun, Oct 25Theater Wit · Lakeview
About this show In a world where facts are manipulated and fear is currency, the truth becomes dangerous. As a new authoritarian government tightens its…
The Factory Theater Presents the World Premiere of “Radical Futures”(opens the event website in a new tab)Sun, Oct 25The Factory Theater · Rogers Park
The Factory Theater and Artistic Director Michael Jones are proud to announce the first production of its 32nd season, the world premiere of B.Z Florida’s…
I.A. Inteligencia Actoral – Destinos: 9th Chicago International Latino Theater Festival(opens the event website in a new tab)Sun, Oct 25Aguijón Theater
I.A. Inteligencia Actoral by Aguijón Theater. Written by: Flavio González Mello. Directed by: Marcela Muñoz A couple of weeks before a theater company opens Hamlet, its…
Brett Goldstein – Chicago, IL – Sex, Death & Small Talk Tour(opens the event website in a new tab)Sun, Oct 25The Chicago Theatre · Loop
Brett Goldstein is bringing his brand-new stand-up comedy tour, “Sex, Death & Small Talk,” to Chicago on Sunday, October 25, 2026, at 7:00 PM.
Refracted Theatre Company Presents “I’m Gonna Marry You Tobey Maguire”(opens the event website in a new tab)Sun, Oct 25The Den Theatre · Wicker Park / Bucktown
Award-winning Refracted Theatre Company is proud to announce the cast and creative team of I’m Gonna Marry You Tobey Maguire, written by Samantha Hurley and…
Omar(opens the event website in a new tab)Sun, Oct 25Lyric Opera of Chicago · Loop
Where memory is preserved, legacy endures. MacArthur “Genius Grant” recipient Rhiannon Giddens and celebrated co-composer Michael Abels deliver a profoundly moving story about the strength…
- Sleeping Beauty & Dvořák Cello Concerto(opens the event website in a new tab)
Sun, Oct 25220 S. Michigan Ave. · Loop
The crown jewel of cello repertoire, Dvořák’s heroic and soulful Cello Concerto marks the return of Jian Wang, a soloist with a lustrous sound and…
The 11pm Show(opens the event website in a new tab)Any weekendiO Theater · Lincoln Park
Continuing the rich tradition of late night improv, join the veteran cast of THE 11PM SHOW every Friday at 11PM as they perform late night, artistic improv…
Harold Night(opens the event website in a new tab)Any weekendiO Theater · Lincoln Park
See the show that started it all, and experience the iO Theater’s groundbreaking, signature improv form: The Harold! This long-running, weekly improv tradition is double-headlined…
360 Sky Yoga(opens the event website in a new tab)Any weekend360 Chicago · Streetervillefrom-$55
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 arrive 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.
- weeklies/2026/10/23(opens the event website in a new tab)
Any weekendThe Green Mill
[Every Fri](https://do312.com/events/weeklies/2026/10/23) [The Green Mill](https://do312.com/venues/the-green-mill)
The Paper Machete(opens the event website in a new tab)Any weekendGreen Mill · Uptown
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.
Wicker Park Farmers Market(opens the event website in a new tab)Any weekendWicker Park Bucktown Chamber of Commerce (at the park) · Wicker Park
If dozens of vendors aren't enough of a draw for you to come to the lively Sunday market at this West Town neighborhood’s namesake park, maybe the weekly complimentary market programming—which includes free yoga, meditation and storytime for kids—will be. The market is also committed to sustainability, with plastic-free vendors and composting. On Thursdays through October 29, check out the market at Walsh Park from 4pm to 8pm.
How HeyWeekend works
- 1. Pick the dates you're both free.
- 2. You each swipe through the same handful of curated nights, privately.
- 3. Anything you both say yes to becomes a match — no negotiating, no long threads.
Stop sending each other links
HeyWeekend learns what you both like and hands you a short list instead of a search page. Invite your person with one link, swipe, and let the matches decide.
Start your weekend