Things to do in Chicago

Friday, Dec 4

Krampus Karnival! presented by the Illumi-Naughtie Occult Burlesque

The Newport Theater

Experience a night of holiday horrors and revelry with the Illumi-Naughtie. Perfect for those who enjoy unique holiday events.

Friday, Dec 4

Thaddeus Tukes The Late Set

Andy's Jazz Club & Restaurant

Join Thaddeus Tukes for a late-night jazz set at Andy's Jazz Club. A great choice for jazz fans looking for a night out.

Friday, Dec 4

Matthew Skoller Chicago Wind feat. Precious Taylor

Rosa's Lounge

Experience a night of blues with Matthew Skoller and Precious Taylor at Rosa's Lounge, featuring late-night performances.

Saturday, Dec 5

Godfrey Holiday Cocktail Fest - Cocktail Tasting

IO Godfrey Rooftop Lounge

Enjoy a variety of seasonal cocktails at this unique tasting event. Perfect for cocktail lovers and holiday enthusiasts.

Saturday, Dec 5

The Winter’s Tale

Navy Pier - Rooftop Terrace

Experience Shakespeare's The Winter's Tale at Navy Pier. A timeless romance perfect for theater lovers.

Saturday, Dec 5

The Winter’s Tale

Navy Pier

Enjoy a performance of The Winter’s Tale at Navy Pier. A classic Shakespearean tale perfect for theater lovers.

Saturday, Dec 5

The Winter’s Tale

Snow Dragon Shavery

Experience Shakespeare's The Winter's Tale. A timeless romance perfect for theater lovers.

Saturday, Dec 5

Comedy Essentials: A One-Hour Standup Jumpstart

The Lincoln Lodge

Try standup comedy with a one-hour workshop at The Lincoln Lodge in Chicago.

Saturday, Dec 5

1st Set With The Pamoja Project

Andy's Jazz Club & Restaurant

Join the Pamoja Project for their first set at Andy's Jazz Club. A must-see for jazz lovers and foodies alike.

Saturday, Dec 5

SATURDAY DECEMBER 5: MATTY CHYMBOR

The Comedy Bar

Enjoy laughs with Matty Chymbor at The Comedy Bar, a great night for comedy lovers in Chicago.

Saturday, Dec 5

Powerpoint Night Live!

The Lincoln Lodge

Bring your friends, lovers, enemies, and fans together for an evening of slide-based edutainment! Learn. Laugh. Leave. <3

Saturday, Dec 5

Bria Skonberg - Jingle Bell Swing

Winter's Jazz Club

Enjoy a festive night of jazz with Bria Skonberg at Winter's Jazz Club in Chicago. Ideal for jazz lovers and holiday music fans.

Saturday, Dec 5

The Lawrence Arms 12th Annual War on Xmas

Metro

Catch The Lawrence Arms and special guests at Metro for their 12th Annual War on Xmas. Ideal for punk rock fans.

Saturday, Dec 5

A Holiday Cabaret with The Uptones

UncommonGround - Lakeview

Enjoy a seated dinner show featuring A Holiday Cabaret with The Uptones at UncommonGround - Lakeview. A festive experience for all.

Saturday, Dec 5

2nd Set With The Pamoja Project

Andy's Jazz Club & Restaurant

Catch the second set of The Pamoja Project at Andy's Jazz Club. A great night for jazz lovers and food enthusiasts.

Saturday, Dec 5

SATURDAY DECEMBER 5: MATTY CHYMBOR

The Comedy Bar

Enjoy laughs with Matty Chymbor at The Comedy Bar, a great night for comedy lovers in Chicago.

Saturday, Dec 5

OSCAR WILSON

Buddy Guy's Legends

Catch Oscar Wilson live at Buddy Guy's Legends. A night of blues not to be missed for music lovers.

Saturday, Dec 5

The Chicago Handshake

The Lincoln Lodge

Experience Chicago's only fully narrative stand-up showcase. Perfect for comedy lovers looking for unique performances.

Saturday, Dec 5

Rising Star 19-Year-Old Harrell "Young Rell" Davenport

Rosa's Lounge

Join 19-year-old Harrell "Young Rell" Davenport for a night of live blues music. Enjoy a relaxed atmosphere with special guests.

Saturday, Dec 5

Feelgood Saturday - DEC 2026

The Whistler

Dance to R&B, Rap, and Soul classics at Feelgood Saturday at The Whistler. Perfect for a lively night out.

Saturday, Dec 5

Top Shelf Comedy Showcase: Chicago's funniest standup comics

The Lincoln Lodge

Enjoy a night of laughs with Chicago's funniest standup comics. Ideal for comedy lovers seeking a good time.

Saturday, Dec 5

Thaddeus Tukes The Late Set

Andy's Jazz Club & Restaurant

Enjoy Thaddeus Tukes' late set at Andy's Jazz Club. A perfect choice for late-night jazz fans.

Saturday, Dec 5

Rising Star 19-Year-Old Harrell "Young Rell" Davenport

Rosa's Lounge

Catch Young Rell Davenport for a late-night blues set with guest musicians. Perfect for blues enthusiasts and late-night outings.

Sunday, Dec 6

World's Carols 2026

Stan Mansion

Rediscover ancient carols at Stan Mansion, celebrating Romanian and international traditions. A beautiful holiday experience.

Sunday, Dec 6

Mad-Good - Songbird Series - Celebrating Signature Voices of Jazz: Shirley Horn

Winter's Jazz Club

Join us for a tribute to Shirley Horn featuring Alyssa Allgood and a talented band at Winter's Jazz Club. A must for jazz enthusiasts.

Sunday, Dec 6

Dr. Fix Me LIVE in Chicago!

The Lincoln Lodge

Enjoy the longest running improv show, Dr. Fix Me, at The Lincoln Lodge. Perfect for fans of unscripted comedy.

Sunday, Dec 6

All Natural: Comedy with a Pregnant Pause

UP Comedy Club

Enjoy a night of stand-up comedy exploring the humor of pregnancy and motherhood. A relatable show for parents and friends.

Sunday, Dec 6

Maggie Winters Has No Ex (a work in progress show)

The Lincoln Lodge

Maggie Winters explores her life in this work-in-progress comedy show. Ideal for fans of stand-up and personal storytelling.

Sunday, Dec 6

All Natural: Comedy with a Pregnant Pause

The Second City

Enjoy a night of stand-up comedy exploring motherhood and pregnancy. A relatable show for all.

Sunday, Dec 6

All Natural: Comedy with a Pregnant Pause

The Second City Training Center

Experience a stand-up comedy show about the quirks of motherhood. Great for anyone connected to a mom.