Holiday events in Chicago, IL

Monday, Nov 23

Hometown Heroes Comedy Show

The Lincoln Lodge

Join us for the Hometown Heroes Comedy Show at The Lincoln Lodge, featuring local comedians for a night of laughs.

Tuesday, Nov 24

Guided Tasting: Cheese for your Holiday Table

Vino &

Enjoy a guided tasting of delicious cheeses paired with wines. A delightful experience for food and wine lovers.

Wednesday, Nov 25

Enjoy Winter at the Pier

Navy Pier

Experience winter festivities at Navy Pier with attractions and shows. Great for holiday fun and family outings.

Wednesday, Nov 25

Wine and Cheese: Perfect Holiday Picks

Vino &

Join us at Eataly to learn about holiday wines and cheeses from experts. Perfect for food lovers and holiday hosts.

Wednesday, Nov 25

Hands-On: Make your Holiday Dessert: Tiramisù

Vino &

Get hands-on with our chef to prepare Tiramisù for your holiday table. A fun workshop for dessert lovers.

Wednesday, Nov 25

Housegiving: A House Music Celebration

Navy Pier

Join the Housegiving celebration at Navy Pier for a night of music and community spirit. A free event for house music fans.

Wednesday, Nov 25

Hands on: Build your Holiday Salumi & Formaggi Board

Vino &

Craft a professional charcuterie and cheese board in this interactive workshop. Perfect for food enthusiasts.

Wednesday, Nov 25

Chris White Trio - A Charlie Brown Thanksgiving!

Winter's Jazz Club

Enjoy a special performance by Chris White Trio at Winter's Jazz Club for a festive Thanksgiving celebration.

Wednesday, Nov 25

Black Wednesday in Pilsen

Simone's

Experience Black Wednesday at Simone's with two rooms and two vibes. A lively night for holiday celebrations.

Wednesday, Nov 25

Blackout Wednesday!

Cell Block Chicago

Join us for Blackout Wednesday at Cell Block Chicago with DJ TheoCratic and no cover charge. A festive night out for adults.

Thursday, Nov 26

Thanksgiving

Lush Wine & Spirits - Roscoe Village

Gather with friends and family for a Thanksgiving celebration filled with food and wine at Lush Wine & Spirits.

Thursday, Nov 26

Thanksgiving Grand Feast

Prime & Provisions Steakhouse

Celebrate Thanksgiving Day with a grand buffet featuring carving stations and traditional sides. Perfect for families and friends.

Thursday, Nov 26

Thanksgiving

ROOF

Elevate your Thanksgiving football tradition at ROOF with a festive atmosphere and great views.

Thursday, Nov 26

Thanksgiving

Mother Hubbard's Sports Pub

Celebrate Thanksgiving with a feast at Mother Hubbard's Sports Pub with friends and family.

Thursday, Nov 26

Thanksgiving

5 Rabanitos Restaurante & Taqueria

Celebrate Thanksgiving Day with a feast at 5 Rabanitos, perfect for friends and family gatherings.

Thursday, Nov 26

Thanksgiving

5 Rabanitos Hyde Park

Bring your friends and family for a celebratory Thanksgiving feast at 5 Rabanitos Hyde Park.

Thursday, Nov 26

Thanksgiving Dinner in Chicago 2026 | A Grand Ballroom Celebration

Trump International Hotel & Tower® Chicago

Experience a memorable Thanksgiving dinner buffet at Trump International Hotel & Tower in Chicago.

Friday, Nov 27

Thanksgiving Feast for 10 People at Home

Fairmont Chicago, Millennium Park

Enjoy a luxurious Thanksgiving feast prepared by our culinary team. Perfect for families celebrating the holiday at home.

Friday, Nov 27

Rudolph Runs Wild

The Second City

Enjoy a festive interactive show with family-friendly comedy and songs. Perfect for kids and adults looking for holiday fun.

Sunday, Nov 29

Wintrust Community Markets

Navy Pier

Shop local at Wintrust Community Markets featuring unique finds from Chicago-area artists and small businesses this holiday season.

Tuesday, Dec 1

A Midsummer Night’s Dream

Navy Pier

Experience Shakespeare’s enchanting comedy at Navy Pier, perfect for families and theater lovers.

Tuesday, Dec 1

A Midsummer Night’s Dream

Navy Pier - Rooftop Terrace

Experience Shakespeare's A Midsummer Night's Dream at Navy Pier. A magical romantic comedy suitable for the whole family.

Tuesday, Dec 1

A Midsummer Night’s Dream

Snow Dragon Shavery

Experience Shakespeare’s magical romantic comedy, A Midsummer Night’s Dream, a delightful treat for the entire family this holiday season.

Wednesday, Dec 2

Sip & Savor: Wine & Cheese for the Holidays

Vino &

Learn about wines and cheeses for the holiday season at Eataly with expert guidance.

Thursday, Dec 3

Sleigh, Sip & Paint - Paint-Your-Own Nutcracker!

Timothy O'Toole's Pub Chicago

Create your own nutcracker at this holiday-themed painting event at O'Toole's. Ideal for those looking for a fun night out.

Thursday, Dec 3

Sip & Savor: Holiday Cocktails & Bites

Vino &

Join a hands-on cocktail-making class with festive drinks and holiday bites.

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

Holidays in the Market Tour: Eat, Shop, Learn

Vino &

Taste and learn about holiday celebrations in this marketplace tour. A delightful experience for food lovers.

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

Sip & Savor: Wine & Cheese for the Holidays

Vino &

Learn about holiday wines and cheeses from experts at Vino &. A delightful event for food and drink enthusiasts.