Lower West Side Christmas Parties 2026

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...

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.

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.

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.

On Saturday, December 5, this Wicker Park bar crawl invites attendees to embrace their naughty side before the holiday season. Participants receive a wristband for access to over eight venues, with no cover charges and exclusive food/drink specials. A coat,...

TRUCE's Holiday Cocktail Lab offers an interactive class on crafting festive holiday cocktails. Participants will learn to prepare components for entertaining, master garnishes, and balance holiday flavors. Attendees will make and enjoy two cocktails.

Adults over 60 can attend a Holiday Sweater Bingo Party & Luncheon with a buffet, bingo games, and entertainment.

Get ready for TBOX 2026, the 30th anniversary of Chicago's legendary '12 Bars of Xmas' pub crawl! This iconic event transforms Wrigleyville into a festive playground with thousands of participants in wild holiday costumes. Kicking off at 10 AM, the...

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

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 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...

Chicago's Wrigleyville neighborhood is the site of a New Year's Eve bar crawl offering an all-access pass to multiple parties. Attendees receive a map, drink specials, and a welcome kit. A pre-party check-in includes additional specials and a social meet-and-greet.

This New Year's Eve bar crawl in Wrigleyville offers admission to over 10 bars. Attendees receive free appetizer buffets, gift cards, live DJs, and a midnight champagne toast. The event is for groups and individuals seeking to visit multiple Chicago...

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...

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...

Celebrate the holiday season with a unique culinary experience at Royal Palms Chicago's Holiday Food Program. They partner with Mad Man Hospitality Group to offer delicious catering for cabana parties from late November through early January. Guests can pre-order gourmet...

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...

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...

Lincoln Park Zoo transforms into a festive wonderland for Adults Night Out: Holidaze. This exclusive 21+ event offers a magical evening under millions of twinkling lights, away from the usual crowds. Guests can enjoy complimentary Ferris wheel and carousel rides,...

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...

Get ready to ring in the New Year with an electrifying disco dance party at The Salt Shed! This event promises a night filled with the greatest hits from ABBA, alongside beloved disco anthems from the 70s and 80s by...