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Music & Comedy
The National Parks at Metro
The National Parks are a husband and wife duo that capture the expansive beauty of the world through soaring melodies and evocative storytelling. The Provo,…
Saturday, October 4th
7:30 p.m. – 10:00 p.m.Metro ChicagoMusic & Comedy
Parker McCollum – What Kinda Man Tour
/w special guests Ashley Cooke & Hudson Westbrook
Saturday, October 4th
7:30 p.m. – 10:30 p.m.Credit Union 1 Amphitheatre
19100 Ridgeland AveMusic & Comedy
Ava Max – Don’t Click Play Tour
Ava Max is bringing the Don’t Click Play Tour to Huntington Bank Pavilion on Saturday, October 4!
Saturday, October 4th
7:30 p.m. – 10:30 p.m.Huntington Bank Pavilion at Northerly Island
1300 S. Linn White Dr.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 4th
8:00 p.m. – 9:30 p.m.Malarkey Comedy Company
1501 N Kingsbury StSaturday, October 4th
8:00 p.m. – 11:00 p.m.Auditorium Theatre
50 East Ida B. Wells DriveMusic & Comedy, Theatre & Performing Arts
Pásele
Celebrating Hispanic Heritage Month, ESCÁNDALO Comedy and iO Theater are bringing a new variety show, “Pásele,” featuring some of Chicago’s best Latine improvisers. The four…
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 4th
9:00 p.m. – 10:00 p.m.The Second City
1616 N. Wells St., Theater on the Second FloorMusic & Comedy
Ahamed Weinberg at The Comedy Bar
2-Item Minimum Per Guest Valid ID Required for Entry First Come, First Served Seating No Outside Food or Beverage Ahamed Weinberg is a Los Angeles-based…
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 4th
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 4th
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 5thThe Harris Theater for Music and Dance
205 East Randolph StreetFestivals, 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 5th
6:00 a.m. – 2:00 p.m.Wolff’s Flea Market
6920 N Mannheim RdFestivals, Fairs & Special Events
Division Street Farmers Market
Fresh seasonal produce, flowers, prepared foods, unique Chicago-made products and rare finds are available at the Division Street Farmers Market.
Sunday, October 5th
7:00 a.m. – 12:00 p.m.30 W. Division St.
30 W. Division St.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…
Festivals, Fairs & Special Events
Maxwell Street Market
Visitors to the Maxwell Street Market will experience an eclectic mix of foods and finds—including handmade crafts, resale housewares, clothing, and much more.
Sunday, October 5th
10:00 a.m. – 3:00 p.m.Maxwell Street Market
800 S. Desplaines St.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,…
Festivals, Fairs & Special Events
Ninth Annual Lincoln Park Wine Fest
Wines from Around the World Featured at 9thAnnual Lincoln Park Wine Fest in Jonquil Park October 3-5 Wine tastings, a food and beverage market, sommeliers on hand…
Sunday, October 5th
11:00 a.m. – 7:00 p.m.Jonquil Park
1001 W. Wrightwood AvenueFestivals, Fairs & Special Events
Simone’s Bar Sweet 16 Anniversary Celebration and 1st Annual Block Party
Event Name:Simone’s Sweet 16 Block Party Admission:Free Description (Event Overview):Celebrate 16 years of community, music, and culture at Simone’s Sweet 16 Block Party in Chicago’s…
Sunday, October 5th
11:30 a.m. – 10:00 p.m.Simone’s bar Simone’s Bar 960 W 18th Street, Chicago, IL 60608
960 W 18th StreetSports & 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 5th
12:00 p.m. – 3:00 p.m.Westin Chicago Northwest
400 Park Blvd.Festivals, Fairs & Special Events, Music & Comedy
Crossing Borders // La Caccina // Holocene
Ear Taxi Festival presents an ear taxi concert. Celebrate contemporary music with powerful performances from Crossing Borders Music, La Caccina, and Holocene. Crossing Borders’ program…
Sunday, October 5th
2:00 p.m. – 5:00 p.m.PianoForte Chicago
1335 South Michigan AvenueFestivals, 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 5th
2:00 p.m. – 5:00 p.m.Meeting Point: Inside the bar at the Congress Plaza Hotel
520 S Michigan Ave.Festivals, Fairs & Special Events, Theatre & Performing Arts
FashionBar The Shows: October 2025 – Modest, Formal, Evening Wear
The closing runway of October 2025, this event presents modest fashion alongside formal and evening wear collections, bringing elegance, refinement, and cultural expression to the…
Sunday, October 5th
2:00 p.m. – 6:00 p.m.Water Tower Place
835 N Michigan AveFestivals, Fairs & Special Events, Tours & Attractions
Resurrection Mary Chicago Halloween Ghost Tour with Pub Stop
Celebrate Halloween with American Ghost Walks on the Resurrection Mary Chicago Ghost Tour with Pub Stop. Discover the legendary spirit of Resurrection Mary on this…
Sunday, October 5th
2:00 p.m. – 6:00 p.m.Meeting Point: Veterans Memorial at Commissioners Park
7795 S 88th Ave.Music & Comedy, Theatre & Performing Arts
Clued In: Where There’s a Will, There’s a Way
YOU’RE INVITED…to bear witness to a fully improvised murder mystery. Six improvisers find themselves trapped on stage with a murderer, and nobody knows who the…

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