Christmas Parties Near Highland 2026

The American Writers Museum hosts Get Lit: Santa’s Book Fair. Attendees can purchase beer, wine, and a signature cocktail, and take photos with Santa Claus. The event supports the AWM’s Write In Youth Education Program.

Ring in the New Year with the unforgettable Pierogi Drop celebration in Whiting, Indiana. This tenth-year event offers a dual experience: an indoor party at the K of C Hall with live entertainment and Polish cuisine, and an outdoor spectacle...

Chicago's Christmas Bar Crawl is set for December 19th, 2026. The event offers 2-3 drinks or shots, no cover charges, and exclusive drink and food specials at participating bars. Attendees receive a stadium party cup, lanyard, Santa hat (for first...

A holiday pub crawl leads participants through River North's bars to the Christkindlmarket. The self-guided event includes a Santa hat, passport map, and a specialty shot at each bar with a beverage purchase.

Chicago's Holiday Cocktail Tasting Festival allows sampling of 8-10 spirits brands' unique holiday cocktail creations, with full cocktails or straight pours available. A small bite buffet, non-alcoholic options, and a live DJ are provided.

Chicago's Official Ugly Sweater Bar Crawl in the West Loop on December 5th, 2026, features hundreds of attendees at Fulton Market venues with drink and food specials.

A 0.5K fun run, the Holiday Winter Dash Beer Run, starts at Goose Island or Midwest Coast Brewing, with participants receiving a craft beverage at each location and a collector's pint glass or swag item. A portion of proceeds benefits...

On December 19, 2026, Chicago's largest holiday bar crawl transforms city bars with hundreds of participants dressed as holiday characters.

Savor a delightful Sunday Gospel Brunch at The Polo Inn, featuring a specially curated menu and live organ music until 2 PM. This unique dining experience offers a festive atmosphere perfect for a weekend treat.

Celebrate an annual holiday tradition at The Polo Inn's Christmas Brunch. This festive event takes place in the historic Old Eagle Room, featuring live organ music playing beloved Christmas favorites. Reservations are essential for this popular celebration, offering a unique...

Experience the magic of the season at Rudolph's Rooftop, a festive winter wonderland atop LondonHouse Chicago. Sip on holiday-inspired cocktails while enjoying breathtaking panoramic views of the city skyline. For an intimate celebration, book a private, heated igloo, perfect for...

Get ready for an unforgettable New Year's Eve at Howl at the Moon's spectacular celebration! They are hosting a night of high-energy entertainment and live music, promising a countdown like no other. Whether you prefer to start with a seated...

Create unforgettable holiday memories at American Girl Chicago's festive teatime tradition. Guests can indulge in a delightful spread of dainty tea sandwiches and sweet treats, complemented by a fun tableside craft activity. Special seating is arranged for dolls, making it...

Frosty's Christmas Bar transforms into a dazzling holiday spectacle, offering an immersive seasonal experience across three levels. Guests can enjoy festive cocktails and a full bar, dance to non-stop holiday music on two dance floors, and capture memories with life-size...