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Upcoming Chicago Events

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Zoo After Dark: Boos & Brews
Oct25
Festivals, Fairs & Special Events

Zoo After Dark: Boos & Brews

Join us for an unforgettable evening of thrills, chills, and specialty drinks at Zoo After Dark: BOOs & Brews, Brookfield Zoo Chicago’s exclusive Halloween event for…

Saturday, October 25th
6:00 p.m.9:30 p.m.
Brookfield Zoo Chicago
3300 Golf Rd
The Infinite Wrench
Oct25
Music & Comedy, Theatre & Performing Arts

The Infinite Wrench

Don’t miss the longest running late-night show in Chicago! At The Infinite Wrench you’ll see 30 original plays in 60 minutes written and performed by…

Saturday, October 25th
7:00 p.m.8:00 p.m.
The Neo-Futurist Theater
5153 N. Ashland Ave.
Teatro Zinzanni
Oct25
Music & Comedy, Theatre & Performing Arts

Teatro Zinzanni

Tickets are on sale Now at https://zinzanni.com/chicago/ for Love, Chaos, & Dinner ! Teatro Zinzanni returns to the vibrant Chicago Loop inside the velvet walls…

Saturday, October 25th
7:00 p.m.10:00 p.m.
Spiegeltent – Cambria Hotel
32 W. Randolph
Halloween Chicago Hauntings Ghost Tour: Explore Paranormal Activity with American Ghost Walks
Oct25
Festivals, Fairs & Special Events, Tours & Attractions

Halloween Chicago Hauntings Ghost Tour: Explore Paranormal Activity with American Ghost Walks

Join the acclaimed Original Chicago Hauntings Ghost Tour by American Ghost Walks. Discover the city’s most haunted sites, including the tragic Eastland disaster location and…

Saturday, October 25th
7:00 p.m.10:00 p.m.
Meeting Point: Inside the bar at the Congress Plaza Hotel
520 S Michigan Ave.
Chicago Composers Orchestra: refracted | mythos
Oct25
Music & Comedy

Chicago Composers Orchestra: refracted | mythos

Showcasing the depth and variety in contemporary American orchestral music through captivating works by American composers Soomin Kim, Paul Novak, Alexa Rinn and Evan Williams.…

Saturday, October 25th
7:30 p.m.8:15 p.m.
Baby Wants Candy! The Original Completely Improvised Musical
Oct25
Music & Comedy, Theatre & Performing Arts

Baby Wants Candy! The Original Completely Improvised Musical

“CRITICS’ PICK. TRULY AMAZING!” – New York Times “BEST VISITING IMPROV COMEDY!”– TimeOut NY “HIGHLY RECOMMENDED!” – The Onion “★★★★★” THEY ARE AN ENTERTAINMENT PHENOMENON AND I…

Saturday, October 25th
7:30 p.m.8:30 p.m.
The Second City
1616 N. Wells St.
Clued In
Oct25
Music & Comedy, Theatre & Performing Arts

Clued In

After getting a single suggestion, the cast of six professional comedians asks the audience to choose a detective. Enjoy as they invent a tale of…

Saturday, October 25th
7:30 p.m.8:30 p.m.
The Second City
1616 N. Wells St., Theater on the Second Floor
Improvised Shakespeare
Oct25
Music & Comedy, Theatre & Performing Arts

Improvised Shakespeare

Critically-acclaimed improvised comedy featuring the language and themes of William Shakespeare

Saturday, October 25th
7:30 p.m.9:00 p.m.
iO Theater
1501 N. Kingsbury St.
Chicago Symphony Orchestra: The Soldier’s Tale
Oct25
Music & Comedy, Theatre & Performing Arts

Chicago Symphony Orchestra: The Soldier’s Tale

Overview Step into the engrossing world of Stravinsky’s The Soldier’s Tale — a Faustian fable about a soldier-fiddler who makes a pact with the devil — in…

Saturday, October 25th
7:30 p.m.9:40 p.m.
Chicago Symphony Center
220 S Michigan Ave
The Nightmare Before Christmas In Concert
Oct25
Festivals, Fairs & Special Events, Music & Comedy, Theatre & Performing Arts

The Nightmare Before Christmas In Concert

Venue: The Auditorium Date: October 25, 2025 Time: 7:30 PM Tickets: $69.50-$99.50 What’s this?! Back by popular demand, see one of Tim Burton’s most celebrated films like never before!…

Saturday, October 25th
7:30 p.m.10:30 p.m.
Auditorium Theatre
50 East Ida B. Wells Drive
ComedySportz Chicago
Oct25
Music & Comedy, Theatre & Performing Arts

ComedySportz Chicago

Chicago’s longest running and best interactive improv comedy experience. ComedySportz is comedy played as a sport, not comedy ABOUT sports (whew). Refs, fouls, points, games…

Saturday, October 25th
8:00 p.m.9:30 p.m.
Malarkey Comedy Company
1501 N Kingsbury St
Ben Schwartz & Friends
Oct25
Music & Comedy

Ben Schwartz & Friends

Ben Schwartz and Friends will come to The Chicago Theatre on Saturday, October 25.

Saturday, October 25th
8:00 p.m.10:00 p.m.
The Chicago Theatre
175 N. State
Here 4 A Bit *Naughty Improv
Oct25
Music & Comedy, Theatre & Performing Arts

Here 4 A Bit *Naughty Improv

Join us again for a whose line styled night of explosive laughter that will titillate your “funny” bone. Fast paced short form improv, hilarious songs,…

Saturday, October 25th
9:00 p.m.10:00 p.m.
The Second City
1616 N. Wells St., Theater on the Second Floor
Best Of Annoyance Sketch
Oct25
Music & Comedy, Theatre & Performing Arts

Best Of Annoyance Sketch

Enjoy the best sketch comedy Chicago has to offer! The Annoyance Theatre has been at the crux of the comedy scene in Chicago for over…

Saturday, October 25th
9:30 p.m.10:30 p.m.
The Annoyance Theatre
851 W. Belmont Ave.
LET’S PLAY A GAME: Chicago’s scariest short-form show
Oct25
Music & Comedy, Theatre & Performing Arts

LET’S PLAY A GAME: Chicago’s scariest short-form show

Who’s Line is it Anyways meets Fear Factor in LETS PLAY A GAME, a new short form show that’s a unique blend of comedy, chaos,…

Saturday, October 25th
10:00 p.m.11:00 p.m.
Annoyance Theatre & Bar
851 W. Belmont Ave., 2nd Fl.
Ear Taxi Festival
Oct26
Festivals, Fairs & Special Events

Ear Taxi Festival

The Ear Taxi Festival 2025, themed “The Composer’s Voice,” is a landmark event showcasing contemporary concert music across Chicagoland from October 3 through November 2,…

Sunday, October 26th
Salute to Cobra Kai
Oct26
Festivals, Fairs & Special Events

Salute to Cobra Kai

Come to the ultimate Salute to Cobra Kai Convention in the Chicago area, to celebrate the hit Netflix series and reignite your karate spirit! Bring…

Sunday, October 26th
Westin O’Hare Hotel
6100 North River Road
Wolff’s Flea Market Opening Day
Oct26
Festivals, Fairs & Special Events

Wolff’s Flea Market Opening Day

Wolff’s Flea Market announces opening day April 20, 2025. Join us for our 34th season outdoors at the Allstate Arena, Rosemont. Sundays 6am-2pm through October…

Sunday, October 26th
6:00 a.m.2:00 p.m.
Wolff’s Flea Market
6920 N Mannheim Rd
Glenwood Sunday Market in Rogers Park
Oct26
Festivals, Fairs & Special Events

Glenwood Sunday Market in Rogers Park

The nonprofit Rogers Park Business Alliance (RPBA) announces 23 local vendors for the 16th anniversary season of the Glenwood Sunday Market, which will operate every…

Sunday, October 26th
9:00 a.m.2:00 p.m.
Glenwood Alfresco
Boo! at the Zoo
Oct26
Festivals, Fairs & Special Events

Boo! at the Zoo

Get ready for a fang-tastic time at BOO! at the Zoo, Brookfield Zoo Chicago’s family-friendly Halloween celebration. This event is packed with not-so-scary thrills, festive decorations,…

Sunday, October 26th
10:00 a.m.5:00 p.m.
Brookfield Zoo Chicago
3300 Golf Rd
Fall Market in Chicago: 170+ Makers, DIY, Food & More
Oct26
Festivals, Fairs & Special Events

Fall Market in Chicago: 170+ Makers, DIY, Food & More

Markets for Makers is coming back to Artifact Events in Chicago on Saturday Oct 25 & Sunday Oct 26 from 11am – 5pm both days!…

Sunday, October 26th
11:00 a.m.5:00 p.m.
Artifact Events
4325 North Ravenswood Avenue
Rappel In Northwest Chicago
Oct26
Sports & Recreation, Tours & Attractions

Rappel In Northwest Chicago

Conquer your limits at 168 feet up and rappel down the Westin Chicago Northwest in Itasca Illinois. Professional equipment provided and no experience needed. Trained…

Sunday, October 26th
12:00 p.m.3:00 p.m.
Westin Chicago Northwest
400 Park Blvd.
Spooktacular 2025 | Clark Street
Oct26
Festivals, Fairs & Special Events

Spooktacular 2025 | Clark Street

Grab your costumes and candy buckets – it’s time for another full weekend of trick-or-treating at Spooktacular in Lincoln Park.  Join the Lincoln Park Chamber…

Sunday, October 26th
1:00 p.m.4:00 p.m.
Lincoln Park
Clark Street, From Armitage to Diversey, Diversey from Lakeview to Orchard
Discover HH Holmes for Halloween: The Devil in the White City Bus Tour by American Ghost Walks
Oct26
Festivals, Fairs & Special Events, Tours & Attractions

Discover HH Holmes for Halloween: The Devil in the White City Bus Tour by American Ghost Walks

Join American Ghost Walks for an immersive 3-hour experience on The Devil in the White City Bus Tour in Chicago. Uncover the chilling tale of…

Sunday, October 26th
2:00 p.m.5:00 p.m.
Meeting Point: Inside the bar at the Congress Plaza Hotel
520 S Michigan Ave.
bean-night

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