Arts & Culture in Chicago, IL

Friday, Dec 4

The Winter’s Tale

Navy Pier - Rooftop Terrace

Catch The Winter's Tale at Navy Pier, a captivating Shakespearean play. A must-see for theater lovers 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.

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

Decempurr Showcase

The Newport Theater

Enjoy a cozy plus size cabaret show at The Newport Theater in Chicago. Perfect for those who appreciate arts and culture.

Sunday, Dec 6

World's Carols 2026

Stan Mansion

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

Monday, Dec 7

Nabala Cafe Monday Movie

Nabala Cafe

Catch a movie at Nabala Cafe in Chicago. A cozy way to enjoy arts and culture.

Wednesday, Dec 9

A Midsummer Night’s Dream

Snow Dragon Shavery

Experience the festive spirit of Shakespeare's romantic comedy, a delightful treat for families this holiday season.

Wednesday, Dec 9

A Midsummer Night’s Dream

Navy Pier

Experience Shakespeare's magical comedy, A Midsummer Night's Dream, at Navy Pier in Chicago.

Wednesday, Dec 9

A Midsummer Night’s Dream

Navy Pier - Rooftop Terrace

Shakespeare's magical romantic comedy, A Midsummer Night's Dream, is a festive treat for the entire family this holiday season.

Thursday, Dec 10

The Winter’s Tale

Navy Pier

Experience Shakespeare's The Winter’s Tale at Navy Pier, a timeless romance for all ages.

Thursday, Dec 10

The Winter’s Tale

Navy Pier - Rooftop Terrace

Experience Shakespeare's The Winter's Tale, a timeless romance that takes you on a fairy tale adventure this holiday season.

Thursday, Dec 10

The Winter’s Tale

Snow Dragon Shavery

Experience Shakespeare’s timeless romance, The Winter’s Tale, in a fairy tale adventure at Snow Dragon Shavery. Perfect for arts and culture lovers.

Friday, Dec 11

Transcendent Frequencies: A Queer & Trans Electronic Open Mic Night

Nabala Cafe

Join us for a queer and trans electronic open mic night at Nabala Cafe. A vibrant space for local artists to showcase their talents.

Saturday, Dec 12

The Winter’s Tale

Navy Pier

Enjoy Shakespeare's The Winter’s Tale at Navy Pier. A classic tale of romance and adventure awaits.

Saturday, Dec 12

The Winter’s Tale

Snow Dragon Shavery

Experience Shakespeare’s timeless romance, The Winter’s Tale, in a fairy tale adventure at Snow Dragon Shavery. Perfect for arts and culture lovers.

Saturday, Dec 12

The Winter’s Tale

Navy Pier - Rooftop Terrace

Experience Shakespeare's The Winter's Tale, a timeless romance that takes you on a fairy tale adventure this holiday season.

Saturday, Dec 12

Holiday Craftathon - Presented by Spinsters

The Lincoln Lodge

Participate in a fun comedy craftathon at The Lincoln Lodge. Great for those looking to finish holiday projects.

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.

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.

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

T(ea) Haus Choreographer Showcase

The Newport Theater

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

Sunday, Dec 20

A Brunch of Drag

Simone's

Join us for a spooktacular Brunch of Drag at Simone's. Enjoy a lively atmosphere and great entertainment.

Sunday, Dec 20

Show & Tell for Grown-Ups: Monthly Showcase of Audience Favorites!

The Lincoln Lodge

Enjoy a showcase of audience favorite presentations at The Lincoln Lodge. A fun event for those who love sharing and learning.

Monday, Dec 21

Nabala Cafe Monday Movie

Nabala Cafe

Join us for a cozy movie night at Nabala Cafe, perfect for film lovers looking for a relaxed evening.

Tuesday, Dec 22

TBOYSKR1PCLUB

The Newport Theater

Join the pop-up skrip club and rent party at The Newport Theater for a night of community and fun. Perfect for local art lovers.

Tuesday, Jan 5

Giggle Hour

The Lincoln Lodge

Experience a unique poetry show that promises to be entertaining and not a total bummer at The Lincoln Lodge.

Sunday, Jan 10

Baddieville's Got Talent: Standup, Drag, Music & More

The Lincoln Lodge

Experience Chicago's wildest talent show featuring standup, drag, and live music at The Lincoln Lodge. A unique night out.