Things to do in Chicago

Sunday, Dec 13

Old Town School's Blues Band showcase

Rosa's Lounge

Experience a showcase of blues music featuring students from the Old Town School of Folk Music at Rosa's Lounge.

Sunday, Dec 13

Anxiety Tonight! (Pigtails are Kosher)

The Newport Theater

Miriam Plotkin returns for her 15th year with a Jewish-themed comedy cabaret. A night filled with laughter and parody songs.

Sunday, Dec 13

Jamie Shriner: Home for the Holidays 12/13/26

The Lincoln Lodge

Join Jamie Shriner for a holiday-themed comedy show at The Lincoln Lodge. Perfect for holiday fun.

Sunday, Dec 13

Duncan Parker

Redhead Piano Bar

Enjoy an evening of live music with Duncan Parker at The Redhead Piano Bar. Perfect for a night out with friends or a cozy date night.

Sunday, Dec 13

Roast Battle Rosemont

Roast Battle Chicago

Enjoy a night of comedy with the Roast Battle in Chicago. Perfect for comedy lovers looking for a fun night out.

Sunday, Dec 13

TBA

Buddy Guy's Legends

Join us for a night of live jazz at Buddy Guy's Legends, featuring a free set followed by a headlining act, perfect for music fans.

Monday, Dec 14

Dinner with Santa at O'Toole's!

Timothy O'Toole's Pub Chicago

Bring the kids for a festive dinner with Santa, featuring a buffet and treats. A great holiday event for families.

Monday, Dec 14

MONDAY DECEMBER 14: LATE NITE MIC WITH VIK PANDYA

The Comedy Bar

Catch Vik Pandya hosting a night of comedy with open mic opportunities. Great for comedy fans and aspiring comedians.

Monday, Dec 14

Holiday Whoobie Whatty?!

The Newport Theater

Enjoy a variety show presented by DKG Production Company at The Newport Theater, featuring diverse performances.

Tuesday, Dec 15

TUESDAY DECEMBER 15: TOMATO THROW SHOW

The Comedy Bar

Experience an interactive comedy show where the audience decides the funniest acts. Perfect for comedy lovers looking for fun.

Wednesday, Dec 16

Dinner with Santa at O'Toole's!

Timothy O'Toole's Pub Chicago

Enjoy an evening with Santa featuring treats and goodie bags. A delightful holiday event for families.

Wednesday, Dec 16

WEDNESDAY DECEMBER 16: CHICAGO'S BEST COMEDY SHOW

The Comedy Bar

Join top comedians for a night of laughter and pizza at The Comedy Bar. Ideal for comedy enthusiasts.

Wednesday, Dec 16

the kates

The Lincoln Lodge

Enjoy a night of comedy with the kates, celebrating female humor and energy. Great for comedy fans.

Wednesday, Dec 16

Rosa's Blues Jam hosted by David Levit (of Million Dollar Blues Band)

Rosa's Lounge

Enjoy a night of blues with David Levit at Rosa's Lounge. Perfect for blues music fans.

Wednesday, Dec 16

Rosa's Blues Jam hosted by David Levit (of Million Dollar Blues Band)

Rosa's Lounge

Join David Levit for a late-night blues jam at Rosa's Lounge. A great night for music lovers.

Thursday, Dec 17

Rooftop Paint and Sip with Bottle and Bottega

Offshore Rooftop

Enjoy a cozy winter Paint and Sip event with a complimentary glass of wine. Perfect for art lovers and social gatherings.

Thursday, Dec 17

CRAZY BINGO - "Live, Laugh, Let's BINGOOO!!!" Edition

Ludlow Liquors

Join the CRAZIEST BINGO night in town at Ludlow Liquors. Cheer for your favorite numbers with friends.

Thursday, Dec 17

THURSDAY DECEMBER 17: OHJAY LAMONT & FRIENDS

The Comedy Bar

Enjoy a night of laughs with OhJay Lamont and friends. A great comedy event for those looking for entertainment.

Thursday, Dec 17

Thursday Night Stand Up Comedy

Laugh Factory

Catch a night of comedy at Laugh Factory in Chicago. Perfect for comedy lovers looking for laughs.

Thursday, Dec 17

T(ea) Haus Choreographer Showcase

The Newport Theater

Support diverse performers at this choreographer showcase. A great event for dance and arts enthusiasts.

Thursday, Dec 17

MANDALYN & THE HUNTERS

Buddy Guy's Legends

Experience live music with Mandalyn & The Hunters at Buddy Guy's Legends. Perfect for music lovers and night out.

Friday, Dec 18

Boogie Wonderland at Howl at the Moon

Howl at the Moon Chicago

Join the high-energy Boogie Wonderland event at Howl at the Moon. Perfect for fans of live music and disco vibes.

Friday, Dec 18

Boogie Wonderland (Chicago)

Howl at the Moon Chicago

Enjoy disco era throwback music and drink features at Howl at the Moon in Chicago. A fun night for lovers of retro music and cocktails.

Friday, Dec 18

FRIDAY DECEMBER 18: CHRISTIAN JOHNSON

The Comedy Bar

Enjoy a night of laughs with Christian Johnson at The Comedy Bar in Chicago. Perfect for comedy enthusiasts.

Friday, Dec 18

Buena Onda Comedy

The Lincoln Lodge

Attend Buena Onda Comedy for a night of Latin comedic talent and good vibes. A must for comedy fans.

Friday, Dec 18

I Said What I Said: A Reality TV-Themed Comedy Show

The Lincoln Lodge

Experience a night of reality and hilarity at The Lincoln Lodge's themed comedy show.

Friday, Dec 18

YOUNG REIL

Buddy Guy's Legends

Enjoy an exciting night with YOUNG REIL and an acoustic set at Buddy Guy's Legends. Ideal for jazz and blues enthusiasts.

Friday, Dec 18

Judah Friedlander Live In Chicago

The Lincoln Lodge

Catch Judah Friedlander performing all-new stand-up at The Lincoln Lodge, a unique comedy experience.

Friday, Dec 18

FRIDAY DECEMBER 18: CHRISTIAN JOHNSON

The Comedy Bar

Catch Christian Johnson performing stand-up at The Comedy Bar for a weekend of laughs in Chicago.

Friday, Dec 18

Cash Box Kings feat. Cameron Webb

Rosa's Lounge

Join Cash Box Kings for a blues night at Rosa's Lounge. A great event for blues enthusiasts.