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The National Parks at Metro
Oct4
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 Chicago
Parker McCollum – What Kinda Man Tour
Oct4
Music & 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 Ave
Ava Max – Don’t Click Play Tour
Oct4
Music & 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.
ComedySportz Chicago
Oct4
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 St
The Psychedelic Furs
Oct4
Saturday, October 4th
8:00 p.m.11:00 p.m.
Auditorium Theatre
50 East Ida B. Wells Drive
Pásele
Oct4
Music & 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…

Saturday, October 4th
8:30 p.m.9:30 p.m.
iO Theater
1501 N. Kingsbury St.
Here 4 A Bit *Naughty Improv
Oct4
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 Floor
Ahamed Weinberg at The Comedy Bar
Oct4
Music & 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…

Saturday, October 4th
9:00 p.m.10:30 p.m.
The Comedy Bar
500 N. LaSalle St.
Best Of Annoyance Sketch
Oct4
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.
LET’S PLAY A GAME: Chicago’s scariest short-form show
Oct4
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.
Ear Taxi Festival
Oct5
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 5th
Wolff’s Flea Market Opening Day
Oct5
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 5th
6:00 a.m.2:00 p.m.
Wolff’s Flea Market
6920 N Mannheim Rd
Division Street Farmers Market
Oct5
Festivals, 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.
Glenwood Sunday Market in Rogers Park
Oct5
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 5th
9:00 a.m.2:00 p.m.
Glenwood Alfresco
Maxwell Street Market
Oct5
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.
Boo! at the Zoo
Oct5
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 5th
10:00 a.m.5:00 p.m.
Brookfield Zoo Chicago
3300 Golf Rd
Ninth Annual Lincoln Park Wine Fest
Oct5
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 Avenue
Simone’s Bar Sweet 16 Anniversary Celebration and 1st Annual Block Party
Oct5
Festivals, 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 Street
Rappel In Northwest Chicago
Oct5
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 5th
12:00 p.m.3:00 p.m.
Westin Chicago Northwest
400 Park Blvd.
Crossing Borders // La Caccina // Holocene
Oct5
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 Avenue
Discover HH Holmes for Halloween: The Devil in the White City Bus Tour by American Ghost Walks
Oct5
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 5th
2:00 p.m.5:00 p.m.
Meeting Point: Inside the bar at the Congress Plaza Hotel
520 S Michigan Ave.
FashionBar The Shows: October 2025 – Modest, Formal, Evening Wear
Oct5
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 Ave
Resurrection Mary Chicago Halloween Ghost Tour with Pub Stop
Oct5
Festivals, 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.
Clued In: Where There’s a Will, There’s a Way
Oct5
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…

Sunday, October 5th
4:00 p.m.5:30 p.m.
The Second City
1616 N. Wells St.
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