Uptown Christmas Parties 2026

Participants dress up in colorful holiday costumes, pajamas, onesies, or ugly sweaters to tour participating Wrigleyville bars. Crawlers can take signature cereal shots of crunchy cereal poured overhead, pose with novelty picture frames, and collect silly themed stickers. The festivities...

Guests indulge in a holiday buffet featuring a feast of festive seasonal treats and enjoy a personal encounter with Santa Claus to share their Christmas wishes. Admission also includes entry to explore the zoo's illuminated grounds during Holiday Magic.

Guests enjoy a festive holiday afternoon tea service held in the Christmas Room. The event features views of the Magnificent Mile parade commencement during the Festival of Lights. Live carolers perform holiday music during the tea service.

Perched high above the Chicago River, this rooftop experience features panoramic views of the skyline and the Magnificent Mile amid twinkling lights and seasonal holiday decor. Guests can gather inside fully enclosed, heated private igloos or enjoy the festive atmosphere...

Guests relax amid festive holiday décor and sweeping views of the Chicago River while enjoying an afternoon tea curated with Chicago’s Rare Tea Cellar. The multi-course service features savory selections such as mini lobster rolls, roast beef Yorkshire puddings, and...

Participants don ugly holiday sweaters and visit multiple bars and nightclubs across Chicago's West Loop. Registered crawlers receive event wristbands granting waived cover charges, holiday-themed drink specials, and select food discounts. Entertainment across venues includes live DJs, a costume contest,...

Participants tour multiple Wicker Park bars using a single wristband that grants cover-free entry along with food and drink specials. The evening includes an ugly sweater photo contest, a holiday scavenger hunt, and an on-site photographer documenting the crawl. Attendees...

Guests can dress up in holiday attire, meet with Santa, and capture the occasion with a photo. The annual tradition features a family-style breakfast served at The Lawn Grill. Attendees also take home a holiday goodie bag.

Local independent Chicago bookstores gather at the American Writers Museum for a holiday-themed book fair for adults. Attendees can browse titles, take photos and listen to holiday stories with Santa, and purchase beer, wine, or the featured Red Nose winter...

Celebrate the season with Mallinckrodt Community Center over a catered luncheon and live entertainment. Attendees have chances to win fabulous door prizes throughout the event. Guests can also participate in the holiday sweater contest by wearing their most festive attire.

Distillery and spirit brand stations mix custom holiday cocktails and provide printed recipe cards for guests to replicate drinks at home. Attendees can order each tasting as a mixed drink or a straight neat pour. The gathering also features a...

Participants complete an untimed 0.5k walk or run along neighborhood sidewalks between Goose Island and Midwest Coast Brewing. Registration provides a craft beverage at both taprooms along with a choice of a collector's pint glass or series swag item. Post-run...

Guests participate in festive rounds of bingo hosted by performer Muffy Fishbasket at Double Clutch Brewing Company. All ticket proceeds are donated to Chicago Drag Story Hour and St. Jude Children's Research Hospital.

Participants receive hands-on instruction from David Mor to craft and drink two elevated holiday cocktails. The class covers preparing drink components in advance, garnishing and presentation, scaling recipes for groups, and balancing warming seasonal flavors with freshness. Each guest also...

Guests are invited to don their most festive holiday sweaters and accessories for an afternoon celebration. The gathering features a lunch buffet, live entertainment, and interactive games of bingo with prizes.

Participants dress in Santa suits, elf outfits, ugly sweaters, or other festive attire to visit participating bars across the city. After checking in, crawlers receive an event wristband and route map granting entry to all stops. Attendees explore the participating...

Participants embark on a self-guided pub crawl through holiday-decorated bars and Christmas-themed pop-ups in Chicago's River North neighborhood, making their way toward the Christkindlmarket. Crawlers travel at their own pace and choose their own venue order. Passes include admission to...

Participants tour multiple Chicago bars dressed in holiday costumes and festive attire. Admission includes drink vouchers, waived cover charges at all participating spots, a souvenir cup, a lanyard, and a digital crawl map. The event also features dedicated mid-party and...

Celebrate high above the city with sweeping indoor views of the Chicago River and skyline. Guests enjoy music, passed appetizers, a four-hour open bar, party favors, confetti, and a champagne toast. Visitors can also head out to the outdoor rooftop...

Participants receive an all-access wristband granting entry to multiple participating bars, lounges, and nightlife venues across Wrigleyville. Admission includes a pre-party social, a digital pub crawl map, event handouts, and drink specials along with welcome shot coupons at select locations....

Participants move between more than ten neighborhood venues within walking distance in Wrigleyville. Admission includes access to all participating bars, complimentary appetizer buffets, live DJs, drink specials, and gift cards to spend during the event. The festivities also feature party...

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,...

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...

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 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...

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...

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...