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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 RdMusic & 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.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. RandolphFestivals, 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.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.Episcopal Cathedral of St. James
65 East Huron StreetMusic & 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…
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 FloorMusic & Comedy, Theatre & Performing Arts
Improvised Shakespeare
Critically-acclaimed improvised comedy featuring the language and themes of William Shakespeare
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 AveFestivals, 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 DriveMusic & 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 StMusic & 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. StateMusic & 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 FloorMusic & 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.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.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 26thThe Harris Theater for Music and Dance
205 East Randolph StreetFestivals, 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…
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 RdFestivals, 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…
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 RdFestivals, 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 AvenueSports & 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.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 OrchardFestivals, 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.

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