Holiday events in Chicago, IL

Friday, Nov 13

A Midsummer Night’s Dream

Navy Pier

Enjoy a festive performance of Shakespeare's A Midsummer Night’s Dream, a delightful treat for families this holiday season.

Friday, Nov 13

A Midsummer Night’s Dream

Snow Dragon Shavery

Enjoy Shakespeare's magical romantic comedy, perfect for the holiday season and family entertainment.

Friday, Nov 13

A Midsummer Night’s Dream

Navy Pier - Rooftop Terrace

Enjoy Shakespeare’s A Midsummer Night’s Dream at Navy Pier, a delightful family-friendly performance this holiday season.

Saturday, Nov 14

Slightly Spooky Movies at the Pier

Navy Pier

Enjoy free indoor movies at Navy Pier's Crystal Gardens featuring family-friendly films on October 17, 24, and 31. Great for families and movie lovers.

Saturday, Nov 14

A Midsummer Night’s Dream

Navy Pier

Experience Shakespeare's magical comedy, A Midsummer Night’s Dream, perfect for families this holiday season.

Saturday, Nov 14

A Midsummer Night’s Dream

Navy Pier - Rooftop Terrace

Enjoy Shakespeare’s magical romantic comedy, perfect for families during the holiday season.

Saturday, Nov 14

A Midsummer Night’s Dream

Snow Dragon Shavery

Enjoy Shakespeare’s magical comedy, A Midsummer Night's Dream, at Snow Dragon Shavery. A family-friendly performance.

Sunday, Nov 15

A Midsummer Night’s Dream

Snow Dragon Shavery

Enjoy Shakespeare’s magical comedy, A Midsummer Night's Dream, at Snow Dragon Shavery. A family-friendly performance.

Sunday, Nov 15

A Midsummer Night’s Dream

Navy Pier - Rooftop Terrace

Enjoy Shakespeare’s magical comedy, A Midsummer Night’s Dream, perfect for families and theater lovers this holiday season.

Sunday, Nov 15

A Midsummer Night’s Dream

Navy Pier

Enjoy Shakespeare’s magical comedy, perfect for families and fans of classic theater during the holiday season.

Sunday, Nov 15

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, Nov 16

Halloween Pottery: Carve Your Own Clay Pumpkin

Color Cocktail Factory Pottery, Date Nights & Art Classes in Chicago

Join this fun beginner-friendly class to create your own clay pumpkin. Suitable for kids and adults alike.

Monday, Nov 16

MONSTER POTTERY! HALLOWEEN LANTERN CLASS

Color Cocktail Factory Pottery, Date Nights & Art Classes in Chicago

Make and paint a fun monster lantern for Halloween in this creative class. Ideal for all skill levels.

Monday, Nov 16

Throw A Pumpkin On The Wheel

Color Cocktail Factory Pottery, Date Nights & Art Classes in Chicago

Make a Halloween pumpkin in this beginner-friendly pottery class. All experience levels welcome.

Tuesday, Nov 17

Vino Days Wine Around

Vino &

Experience over 20 wine tastings and holiday bites. Ideal for wine lovers preparing for the festive season.

Wednesday, Nov 18

Wine and Cheese: Perfect Holiday Picks

Vino &

Learn about holiday wine and cheese pairings from experts. A must for anyone preparing for festive gatherings.

Wednesday, Nov 18

A Midsummer Night’s Dream

Navy Pier

Enjoy Shakespeare’s A Midsummer Night’s Dream, a festive family-friendly performance.

Wednesday, Nov 18

A Midsummer Night’s Dream

Snow Dragon Shavery

Experience Shakespeare's magical romantic comedy, A Midsummer Night's Dream, perfect for the whole family.

Wednesday, Nov 18

A Midsummer Night’s Dream

Navy Pier - Rooftop Terrace

Experience Shakespeare's magical comedy, A Midsummer Night’s Dream, at Navy Pier. A festive treat for the whole family.

Thursday, Nov 19

Friendsgiving Float-In

Trump International Hotel & Tower® Chicago

Celebrate Friendsgiving with rom-com classics and a festive buffet at this unique float-in event.

Thursday, Nov 19

Vino Days Wine Around

Vino &

Experience over 20 wine tastings and holiday bites at Vino &. Perfect for wine enthusiasts.

Thursday, Nov 19

A Midsummer Night’s Dream

Snow Dragon Shavery

Enjoy Shakespeare's magical comedy, A Midsummer Night's Dream, perfect for the whole family in Chicago.

Thursday, Nov 19

A Midsummer Night’s Dream

Navy Pier

Enjoy Shakespeare's magical comedy, perfect for families and fans of classic theatre. A delightful holiday treat for all ages.

Thursday, Nov 19

A Midsummer Night’s Dream

Navy Pier - Rooftop Terrace

Enjoy Shakespeare's magical comedy, A Midsummer Night's Dream, at Navy Pier. A festive treat for families and theater lovers.

Friday, Nov 20

Christkindlmarket Opens

Lush Wine & Spirits - Roscoe Village

Celebrate the arrival of mulled wine season at Christkindlmarket in Chicago. A must-visit for holiday enthusiasts and wine lovers.

Saturday, Nov 21

Lights Festival Starts Here

The Shops at North Bridge

Celebrate the Wintrust Magnificent Mile Lights Festival with shopping, dining, and festive fun. Enjoy exclusive promotions and holiday experiences.

Saturday, Nov 21

RiverNorth Pole 2026 | Santa, Live Reindeer & Holiday Magic for St. Jude

Trump International Hotel & Tower® Chicago

Join us for a family fun day with Santa and Mrs. Claus at the River North Pole event.

Saturday, Nov 21

Wine and Cheese: Perfect Holiday Picks

Vino &

Learn about wines and cheeses for the holiday season at Eataly. Great for foodies and holiday planners.

Saturday, Nov 21

A Front-Row Affair | The Magnificent Mile Lights Festival At Rebar

Trump International Hotel & Tower® Chicago

Experience Chicago's Lights Festival from a unique vantage point at Rebar. Ideal for holiday enthusiasts.

Saturday, Nov 21

Winter Fireworks

Navy Pier

Catch Navy Pier's free winter fireworks show every Saturday at 8 PM from November 28 to December 26. A festive experience for all.