Holiday events in Chicago, IL

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

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.

Sunday, Dec 6

World's Carols 2026

Stan Mansion

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

Tuesday, Dec 8

Ante Up Holiday Special

UP Comedy Club

Enjoy a night of longform improv comedy with multiple teams competing for laughs and prizes. A fun night out.

Tuesday, Dec 8

Ante Up Holiday Special

The Second City

Enjoy longform improv comedy at The Second City in Chicago with the Ante Up Holiday Special. A fun night for comedy fans.

Tuesday, Dec 8

Ante Up Holiday Special

The Second City Training Center

Join the Ante Up Holiday Special for improv comedy at The Second City Training Center in Chicago. Great for comedy lovers.

Tuesday, Dec 8

Chris White Trio + 3-person Choir: A Charlie Brown Christmas!

Winter's Jazz Club

Celebrate the holidays with a performance of A Charlie Brown Christmas at Winter's Jazz Club. Perfect for jazz and holiday fans.

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.

Wednesday, Dec 9

Caroline & Laura's Holiday Spectacular!

The Newport Theater

Join Caroline & Laura for their 10th Holiday Spectacular at The Newport Theater. A festive event filled with music and fun.

Friday, Dec 11

Holiday Festa

Vino &

Celebrate the season at Holiday Festa with festive bites and Italian wines. A perfect event for food and wine lovers.

Friday, Dec 11

Happy Holidays with Wicked Drawl

UncommonGround - Lakeview

Enjoy an intimate dinner show featuring Wicked Drawl at UncommonGround - Lakeview. A festive night for music lovers.

Saturday, Dec 12

Ugliest Christmas Sweater Party

Z Bar

Join the Ugliest Christmas Sweater Party at Z Bar in Chicago for a fun night of holiday spirit and prizes for the best sweaters.

Saturday, Dec 12

Breakfast With Santa

900 North Michigan Shops

Enjoy a festive buffet and holiday magic at Breakfast With Santa. A delightful event for families and kids.

Saturday, Dec 12

Sip & Savor: Wine & Cheese for the Holidays

Vino &

Learn about holiday wines and cheeses from experts at Eataly in Chicago during this tasting event.

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.

Saturday, Dec 12

Jay Bragg Presents: Christmas in New Vaudeville!

UncommonGround - Lakeview

Experience an intimate dinner show with Jay Bragg at UncommonGround - Lakeview. A festive night for music lovers.

Saturday, Dec 12

JIMMY BURNS & SOUL MESSAGE BAND – Delmark Holiday Party

Buddy Guy's Legends

Enjoy soulful sounds from Jimmy Burns & Soul Message Band at Buddy Guy's Legends during the Delmark Holiday Party. A night for jazz and blues lovers.

Sunday, Dec 13

Dine & Demo: Classic Italian Holiday Dishes

Vino &

Gather for an Italian holiday feast with a three-course meal and wine at Vino &. Great for food lovers and families.

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.

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.

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.

Thursday, Dec 17

Flash Class: Festive Wines

Vino &

Join our wine expert for a guided tasting of Italian wines perfect for the holiday table.

Saturday, Dec 19

Sip & Savor: Holiday Cocktails & Bites

Vino &

Join a hands-on cocktail-making class and enjoy perfect holiday bites. Ideal for those looking to learn festive drink recipes.

Sunday, Dec 20

Demo & Dine: Holiday Desserts

Vino &

Learn to make festive holiday desserts in this demonstration class. Great for those wanting to enhance their holiday baking skills.

Tuesday, Dec 22

Hands-on: Gnocchi al Burro e Tartufo

Vino &

Learn to make Gnocchi al Burro e Tartufo in this hands-on cooking class. Perfect for food lovers looking to enhance their culinary skills.

Wednesday, Dec 23

Holiday Fun with Fondue

Vino &

Join us for a fun evening of Italian fonduta cooking demonstration. A delightful experience for food lovers during the holidays.

Thursday, Dec 24

Christmas Eve

Lush Wine & Spirits - Roscoe Village

Celebrate Christmas Eve at Lush Wine & Spirits. Enjoy festive drinks and a warm atmosphere with friends.

Thursday, Dec 24

Hands-On: Make your Holiday Dessert: Tiramisù

Vino &

Learn to make Tiramisù for the holidays in this hands-on class. Perfect for those looking to impress at their holiday gatherings.