Things to do in Chicago

Thursday, Oct 29

Jam Sandwich

UP Comedy Club

Enjoy a night of spontaneous improv comedy at The Second City with Jam Sandwich. A fun experience for comedy lovers.

Thursday, Oct 29

From Lava to Vine: A Volcanic Wine Dinner

The Village

Explore volcanic wines with a curated dinner at The Village. Perfect for wine enthusiasts and food lovers.

Friday, Oct 30

Lev Fer ONE NIGHT ONLY

The Lincoln Lodge

Enjoy a night of hilarious standup comedy with Lev Fer at The Lincoln Lodge. A great option for comedy fans.

Friday, Oct 30

THURSDAY OCTOBER 29: OHJAY LAMONT & FRIENDS

The Comedy Bar

Enjoy a night of laughs with OhJay Lamont and friends at The Comedy Bar, a must-see comedy event in Chicago.

Friday, Oct 30

Exotic Erotic presented by Gender F*cked Productions and KazMo Universe

The Newport Theater

Celebrate culture and community through burlesque and performance art at Exotic Erotic in Chicago. A unique night of entertainment.

Friday, Oct 30

Brew Comedy: New Material Night

Laugh Factory

Catch new material from comedians at Brew Comedy night at Laugh Factory. Ideal for comedy enthusiasts.

Friday, Oct 30

A Night With Xscape, Plies, Ann Marie, Case and Pleasure P

The Chicago Theatre

See Xscape: Symphony of Love with a live orchestra at The Chicago Theatre. A unique blend of R&B and orchestral music.

Friday, Oct 30

NIGEL MACK

Buddy Guy's Legends

Experience an electrifying performance by Nigel Mack at Buddy Guy's Legends. A great night for live music enthusiasts.

Friday, Oct 30

Research & Development

The California Clipper

Experience a night of techno and club music at The California Clipper. Ideal for electronic music fans.

Friday, Oct 30

Lev Fer ONE NIGHT ONLY

The Lincoln Lodge

Enjoy a night of hilarious standup comedy with Lev Fer at The Lincoln Lodge. A must-see for comedy fans.

Friday, Oct 30

Jen Porter

Redhead Piano Bar

Enjoy a late-night performance by Jen Porter at The Redhead Piano Bar in Chicago.

Friday, Oct 30

Halloween Party at Howl at the Moon

Howl at the Moon Chicago

Join the Halloween weekend party at Howl at the Moon with live music and a costume contest. A lively night for partygoers.

Friday, Oct 30

Halloween Party at Howl at the Moon Chicago

Howl at the Moon Chicago

Celebrate Halloween with live music and a costume contest at Howl at the Moon Chicago. A lively night for party-goers.

Saturday, Oct 31

DREW NICKENS & FRIENDS

RED ROOM Comedy Club

Enjoy a lively stand-up comedy showcase featuring Drew Nickens and friends at the RED ROOM Comedy Club in Chicago.

Saturday, Oct 31

Nervous Laughter Comedy Show: Laugh now, overthink later

The Lincoln Lodge

Experience a night of storytelling and standup comedy with local Chicago comedians at The Lincoln Lodge. Ideal for comedy enthusiasts.

Saturday, Oct 31

Don Lemon & DL Hughley: DL + DL 'Anything Goes'

The Chicago Theatre

See Don Lemon and DL Hughley perform their comedy show at The Chicago Theatre. Perfect for comedy fans looking for a night of laughs.

Saturday, Oct 31

HOP LATE NIGHT TIL 4AM with Touss + DJ Eves

Hopsmith Chicago

Dance all night with DJs Touss and Eves at Hopsmith Tavern. Ideal for party-goers and late-night enthusiasts.

Saturday, Oct 31

BLUES PEOPLE

Buddy Guy's Legends

Enjoy an electrifying night of blues with BLUES PEOPLE at Buddy Guy's Legends in Chicago. Perfect for live music fans.

Saturday, Oct 31

The Simple Remedy

Broken Hearts

Experience a night of storytelling through music with The Simple Remedy. Perfect for fans of soul and blues.

Saturday, Oct 31

Gay for Pay

The Lincoln Lodge

Experience a summer camp-themed night of standup, improv, and burlesque at The Lincoln Lodge in Chicago.

Saturday, Oct 31

Slightly Spooky Saturday

Navy Pier

Celebrate Halloween with trick-or-treating and live entertainment at Navy Pier. A festive event for families.

Saturday, Oct 31

Spellbound: Pole Dancing + Burlesque Show

The Newport Theater

Experience an evening of mystery and mysticism with a pole dancing and burlesque show at The Newport Theater.

Saturday, Oct 31

You Win Some, You Dim Sum: an uplifting comedy show

The Lincoln Lodge

Join Chicago Standups for an uplifting comedy show that celebrates everyday wins. Perfect for anyone looking for a good laugh.

Sunday, Nov 1

SATURDAY OCTOBER 31: SERGEI PUTINSKI

The Comedy Bar

The hilarious Sergei Putinski headlines a night of laughs at The Comedy Bar, right off the Magnificent Mile!

Sunday, Nov 1

The Rocky Horror Picture Show

The Chicago Theatre

See The Rocky Horror Picture Show at The Chicago Theatre for a spooktacular night. Perfect for fans of cult classic cinema.

Sunday, Nov 1

I|O Godfrey Halloween 2026

IO Godfrey Rooftop Lounge

Join the Halloween celebration at IO Godfrey Rooftop Lounge in Chicago. A must for fans of themed nightlife and music.

Sunday, Nov 1

Do The Needful - Live on Halloween

Skylark

Enjoy a vibrant Bollywood performance by Do The Needful this Halloween. Perfect for music lovers and dance enthusiasts.

Sunday, Nov 1

SATURDAY OCTOBER 31: GOOFAZZ HALLOWEEN COMEDY SHOW

The Comedy Bar

Join the Goofazz Halloween Comedy Show for a night of laughs and costumes at The Comedy Bar in Chicago.

Sunday, Nov 1

HALLOWEEN LATE NIGHT TIL 5AM with DJ N. Harmonix + Devinci Spinns

Hopsmith Chicago

Dance from 9 PM to 5 AM at Hopsmith Tavern with DJs N. Harmonix and Devinci Spinns. Perfect for Halloween party-goers.

Sunday, Nov 1

Brandon Good's Halloween Spooktackular with Roxy Swain as Dolly Parton

Broken Hearts

Enjoy a lively Halloween night with Brandon Good and Roxy Swain performing as Dolly Parton. Great for country music fans.