Things to Do in Chicago This Weekend October 21 23 2022 Thrillist
Things to Do in Chicago This Weekend: October 21-23, 2022 - ThrillistSkip to main contentLike Thrillist on Facebook.Follow Thrillist on Instagram.Follow Thrillist on Twitter.Follow Thrillist on Snapchat.Subscribe to Thrillist on YouTube.Follow Thrillist on TikTok.SUBSCRIBEGo to NavigationChicagoEventsEntertainmentAdvertiser Content From
Newport Theater
Kicking things up a notch from the standard sexy witch costume this Halloween is this vampire burlesque-inspired live show featuring leading lights in the local burlesque scene along with mistresses of ceremonies Sally Marvel and Sio Bast. Vampire costumes encouraged.
Cost: $15 - $40
Various locations
This weekend brings plenty of laughs along for the ride with a standout selection of visiting comics including Demetri Martin at the Vic, Michael Ian Black at Den Theatre, and D.L. Hughley at Chicago Improv Comedy Club. Choose wisely.
Cost: Varies
Gallagher Way
While there’s no October baseball at Wrigley Field, this family-friendly event pops up in the Gallagher Way space with live entertainment, Halloween slime, pumpkins, lawn games, haystack bowling, a strolling magic show, and enough Halloween candy to last until next Halloween. Or the car ride home.
Cost: Free admission
Prairie Center for the Arts
Seven years in the music business is a long time… let alone 70 years. Legendary Chicago blues label Delmark Records has been doing its thing for exactly that long, a feat it will be celebrating with a star-studded lineup of live blues acts including Mike Wheeler and Dave Specter.
Cost: $32 - $34
Subterranean
This event taking place downstairs at Subt not only features live performances, but also artist vendors, live painting, and a “celebrity guest.” Presented by WFAB 94.5, you might even discover a new radio favorite.
Cost: $20
Chicago Cultural Center
More than a dozen Chicagoland artists and bands will have the chance to showcase their talents in front of music industry A&R reps from record labels such as Motown Records and organizations such as Sofar Sounds. Masked Singer this ain’t.
Cost: Free
Various locations
Chicago Humanities Festival’s Fall Season kicks into high gear this weekend with a wide range of speakers from Phil Rosenthal and Jeff Garlin to April Ryan and Margo Price. Rosenthal will be offering cooking advice and Ryan will join in a conversation called “Black Women Will Save the World,” while Garlin will chat about his Chicago roots.
Cost: Varies
Theater on the Lake
Enjoy a beautiful fall Sunday at the lake equipped with the full arsenal of brunch delights including brunch bites, themed cocktails, lawn games, live demonstrations, and a Bloody Mary competition. Kick off the event early with yoga and a fun run on the lake.
Cost: $35 - $95
Reggie’s
This year’s annual Haunted House Trip will have guests traveling to Zion to experience the sprawling Dungeon of Doom with VIP front-of-line entry along with plenty of beers and booze on the bus to and from Reggie’s to help calm those nerves.
Cost: $60
Sleeping Village
This first-ever dog drag parade and costume contest hosted by Lucy Stoole will see pups strutting their stuff on the runway while competing for prizes, with pet portraits and doggie treat bags also available.
Cost: Free admission Want more Thrillist? Follow us on Instagram, Twitter, Pinterest, YouTube, TikTok, and Snapchat.Jay Gentile is an award-winning freelance journalist specializing in travel, food & drink, culture, events and entertainment stories. In addition to Thrillist, you can find his work in The Washington Post, The Guardian, CNN Travel, Chicago Tribune, Lonely Planet, VICE, Outside Magazine and more. Follow @thejaygentile.By signing up, I agree to the Terms and Privacy Policy.
Everything Fun You Can Do in Chicago This Weekend
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
By Jay Gentile Updated on 10/20/2022 at 2:58 PMAdvertiser Content From Gallagher Way ChicagoIf you like haunted houses, vampire burlesque, and Bloody Marys, you’ll love this weekend. But if you’d rather see some live comedy, speaker panels and a doggie drag parade, well, there’s that too. Here’s everything fun you can do in Chicago this weekend.Feast your eyes on some vampire burlesque at Theatres de Vampires
Friday, October 21Newport Theater
Kicking things up a notch from the standard sexy witch costume this Halloween is this vampire burlesque-inspired live show featuring leading lights in the local burlesque scene along with mistresses of ceremonies Sally Marvel and Sio Bast. Vampire costumes encouraged.
Cost: $15 - $40
See a trio of funny dudes at stand-ups gigs around town
Friday, October 21 - Sunday, October 23Various locations
This weekend brings plenty of laughs along for the ride with a standout selection of visiting comics including Demetri Martin at the Vic, Michael Ian Black at Den Theatre, and D.L. Hughley at Chicago Improv Comedy Club. Choose wisely.
Cost: Varies
Bring the whole fam out to the Pumpkin Party at Gallagher Way
Saturday, October 22Gallagher Way
While there’s no October baseball at Wrigley Field, this family-friendly event pops up in the Gallagher Way space with live entertainment, Halloween slime, pumpkins, lawn games, haystack bowling, a strolling magic show, and enough Halloween candy to last until next Halloween. Or the car ride home.
Cost: Free admission
Commemorate a momentous milestone at Delmark Records 70th Anniversary Blues Revue
Saturday, October 22Prairie Center for the Arts
Seven years in the music business is a long time… let alone 70 years. Legendary Chicago blues label Delmark Records has been doing its thing for exactly that long, a feat it will be celebrating with a star-studded lineup of live blues acts including Mike Wheeler and Dave Specter.
Cost: $32 - $34
Check out live painting as you spit mad rhymes at Hip Hop Culture Fest
Saturday, October 22Subterranean
This event taking place downstairs at Subt not only features live performances, but also artist vendors, live painting, and a “celebrity guest.” Presented by WFAB 94.5, you might even discover a new radio favorite.
Cost: $20
See budding music industry stars at the Chicago Made A& R Auditions Showcase
Saturday, October 22Chicago Cultural Center
More than a dozen Chicagoland artists and bands will have the chance to showcase their talents in front of music industry A&R reps from record labels such as Motown Records and organizations such as Sofar Sounds. Masked Singer this ain’t.
Cost: Free
See Phil Rosenthal Jeff Garlin and April Ryan at Chicago Humanities Festival
Saturday, October 22 - Sunday, October 23Various locations
Chicago Humanities Festival’s Fall Season kicks into high gear this weekend with a wide range of speakers from Phil Rosenthal and Jeff Garlin to April Ryan and Margo Price. Rosenthal will be offering cooking advice and Ryan will join in a conversation called “Black Women Will Save the World,” while Garlin will chat about his Chicago roots.
Cost: Varies
Hit a massive brunch on the lake and maybe do a little yoga at Bloody Mary Fest
Sunday, October 23Theater on the Lake
Enjoy a beautiful fall Sunday at the lake equipped with the full arsenal of brunch delights including brunch bites, themed cocktails, lawn games, live demonstrations, and a Bloody Mary competition. Kick off the event early with yoga and a fun run on the lake.
Cost: $35 - $95
Take a road trip to Dungeon of Doom at the Reggie s Haunted House Trip
Sunday, October 23Reggie’s
This year’s annual Haunted House Trip will have guests traveling to Zion to experience the sprawling Dungeon of Doom with VIP front-of-line entry along with plenty of beers and booze on the bus to and from Reggie’s to help calm those nerves.
Cost: $60
Let your pooch get in on the fun at the Doggie Day Drag Parade & Costume Contest
Sunday, October 23Sleeping Village
This first-ever dog drag parade and costume contest hosted by Lucy Stoole will see pups strutting their stuff on the runway while competing for prizes, with pet portraits and doggie treat bags also available.
Cost: Free admission Want more Thrillist? Follow us on Instagram, Twitter, Pinterest, YouTube, TikTok, and Snapchat.Jay Gentile is an award-winning freelance journalist specializing in travel, food & drink, culture, events and entertainment stories. In addition to Thrillist, you can find his work in The Washington Post, The Guardian, CNN Travel, Chicago Tribune, Lonely Planet, VICE, Outside Magazine and more. Follow @thejaygentile.By signing up, I agree to the Terms and Privacy Policy.