Things to do in Chicago

Sunday, Oct 4

Mad-Good - Songbird Series - Celebrating Signature Voices of Jazz: Nancy Wilson

Winter's Jazz Club

Enjoy a night of jazz celebrating the iconic Nancy Wilson. A must for jazz lovers and music enthusiasts in Chicago.

Sunday, Oct 4

Dr. Fix Me LIVE in Chicago!

The Lincoln Lodge

Enjoy a hilarious improvised talk show inspired by classic daytime TV. Great for fans of comedy and unique performances.

Sunday, Oct 4

SUNDAY OCTOBER 4: KEVIN WILLIAMS

The Comedy Bar

Enjoy a night of laughs with Kevin Williams at The Comedy Bar. Perfect for comedy fans looking for a fun night out.

Sunday, Oct 4

Hot 5 Comedy Show

The Lincoln Lodge

Laugh with five of Chicago's hottest comedians at this entertaining comedy show.

Monday, Oct 5

Natalie Lynch & the Hired Guns

Broken Hearts

Experience an unforgettable night with Natalie Lynch & the Hired Guns blending country, rock, folk, and blues at Broken Hearts.

Monday, Oct 5

SIBLING BONDING Comedy Show

RED ROOM Comedy Club

Enjoy a night of laughs at the SIBLING BONDING Comedy Show at the RED ROOM Comedy Club. Great for comedy lovers.

Monday, Oct 5

The Ultimate Beyoncé Experience

The Newport Theater

Enjoy a tribute to Beyoncé at The Newport Theater. Perfect for fans of live music and tribute shows.

Monday, Oct 5

Sunday Night Stand Up Comedy

Laugh Factory

Catch up-and-coming comedians at Laugh Factory in Chicago. A fun night for comedy enthusiasts.

Monday, Oct 5

Jeopardy Bar League

Trader Todd's

Join the Jeopardy Bar League for a fun trivia night at Trader Todd's. Ideal for quiz enthusiasts.

Monday, Oct 5

Sunday Best

The Lincoln Lodge

Enjoy a 90-minute showcase featuring top Chicago comedians. A great way to spend a Sunday evening with laughter and fun.

Monday, Oct 5

Cuffed & Confused

UP Comedy Club

Explore the ups and downs of relationships in this sketch comedy show. A fun night of laughter awaits.

Monday, Oct 5

Pop Quiz Hot Shot

The Lincoln Lodge

Chicago's own pleasantly pointless pop culture panel show.

Monday, Oct 5

Skyler Higley

The Lincoln Lodge

Catch comedian Skyler Higley live at The Lincoln Lodge. A great night for comedy enthusiasts.

Monday, Oct 5

Hammered Herstory: Chicago's Funniest Drunk Comedy Storytelling

The Lincoln Lodge

Join the Hammered Herstory comedy show at The Lincoln Lodge for a night of storytelling and laughs. Great for comedy fans.

Monday, Oct 5

SUNDAY OCTOBER 4: JUSTIN WHITEHEAD

The Comedy Bar

Laugh the night away with Justin Whitehead at The Comedy Bar. A must-see for comedy enthusiasts in Chicago.

Monday, Oct 5

Comedians That Are Gay

The Lincoln Lodge

Experience a comedy show featuring talented queer comedians. A must-see event for comedy lovers in Chicago.

Monday, Oct 5

Surfin' Bird - Live

Skylark

Enjoy Surfin' Bird at Skylark, a lively music event capturing summer vibes. Perfect for those wanting a fun night out in Chicago.

Monday, Oct 5

DAVE WELD

Buddy Guy's Legends

Experience an electrifying night with Dave Weld at Buddy Guy's Legends, featuring a free jazz set before the main event.

Monday, Oct 5

Sunday Night Stand Up Comedy

Laugh Factory

Enjoy a night of comedy at Laugh Factory in Chicago. A great way to unwind and laugh.

Monday, Oct 5

Creepin’ It Real: A Spooky Sketch Show

UP Comedy Club

Enjoy a Halloween themed sketch comedy show in Chicago. Perfect for fans of spooky humor and comedy lovers alike.

Monday, Oct 5

Late Night Concert Series w/Andrew Toombs

Andy's Jazz Club & Restaurant

Enjoy a late-night concert featuring Andrew Toombs in a cozy jazz club. Ideal for jazz lovers and night owls.

Monday, Oct 5

Jeremy Bell

Redhead Piano Bar

Experience an exciting night with Jeremy Bell at the Redhead Piano Bar, perfect for late-night entertainment.

Monday, Oct 5

Tony Hays

Redhead Piano Bar

Join us for an electrifying night with Tony Hays at The Redhead Piano Bar, filled with great music and drinks.

Monday, Oct 5

Sundays and Mondays - Open for Special Events Only

Rosa's Lounge

Rosa's Lounge is open for special events on Sundays and Mondays. Contact us for event inquiries.

Monday, Oct 5

1st Set With The Heritage Jazz Orchestra

Andy's Jazz Club & Restaurant

Catch the 1st set with The Heritage Jazz Orchestra at Andy's Jazz Club in Chicago.

Monday, Oct 5

2nd Set With The Heritage Jazz Orchestra

Andy's Jazz Club & Restaurant

Enjoy the 2nd set with The Heritage Jazz Orchestra at Andy's Jazz Club in Chicago.

Monday, Oct 5

Monday Drink Special: $7 22oz Fatpours

Hopsmith Chicago

Enjoy $7 draft beers in 22oz mugs every Monday at Hopsmith. A great way to kick off your week.

Monday, Oct 5

Happy Hour in Gold Coast at Hopsmith

Hopsmith Chicago

Enjoy daily drink specials and happy hour at Hopsmith Chicago, known for its friendly staff and vibrant atmosphere.

Monday, Oct 5

Happy Hour

Woodie's Flat

Enjoy drink and food specials during Happy Hour at Woodie's Flat. A great spot to unwind after work.

Monday, Oct 5

1st Set With The Blueshift Big Band

Andy's Jazz Club & Restaurant

Enjoy live jazz music with The Blueshift Big Band at Andy's Jazz Club. A perfect night for jazz lovers in Chicago.