Plan a whirlwind group holiday trip to Chicago. See dazzling light displays at Navy Pier and Lincoln Park Zoo. Explore the authentic German Christkindlmarket in the Loop. Go ice skating in Millennium Park. And catch beloved holiday shows like A Christmas Carol and The Nutcracker. Our three-day itinerary makes it easy for your group to experience the best of Chicago’s favorite holiday traditions.
Day 1/Daytime
Introduce your group to Chicago’s famed architectural treasures. Book a private walking or bus tour with an expert guide from the Chicago Architecture Center. Be sure to allow time for viewing the fascinating exhibits at the Center before or after your tour.
Stroll the charming holiday windows along State Street followed by lunch in the legendary Walnut Room under the sparkling Great Tree at Macy’son State Street. Join the store’s Holiday Traditions Tour, offered from November to January, and learn the stories behind its animated holiday windows and fabulous decorations.
Bring your group to one of the city’s downtown ice skating rinks, boasting awesome city views as their backdrops. Glide on the winding Maggie Daley ParkIce Skating Ribbon. Or practice figure eights on the McCormick Tribune Ice Rink in Millennium Park. Advance ice skating reservations are required.
Day 1/Evening
Millennium Park hosts a series of winter events and activities that groups will enjoy. Bundle up for wintry selfies at the shiny Cloud Gate sculpture, affectionately known as “The Bean.” Attend the city’s official Christmas tree-lighting ceremony on Nov. 21, 2025. And catch holiday dance, music, and stage shows at the Harris Theater.
Book a dinner cruise aboard one of the City Cruises boats departing from Navy Pier. After the cruise, stay at Navy Pier for Light Up the Lake, held from late November to early January. Your group will be delighted by the outdoor light displays, holiday-themed drone shows, and craft and artisan vendors. Visiting on a Saturday? You’ll be treated to a light-up-the-sky fireworks display.
Chicago is known for its exceptional holiday theatre offerings. Reserve group seats and attend a classic version of A Christmas Carol at the Goodman Theatre, the funny Elf the Musical presented by Broadway In Chicago at the Auditorium Theatre, or a magical performance of The Nutcracker by the Joffrey Ballet.
Day 2/Daytime
Bring your group to Christkindlmarket Chicago, a tradition since 1996 that’s modeled after outdoor holiday markets in Germany. Join a behind-the-scenes Culture & Cheer Tour, shop for handmade gifts at the quaint wooden vendor stalls, sip hot cider or spiced wine, and dine on traditional German fare in the lodge, accompanied by a live oompah band.
With over 430 retailers offering everything from luxury goods to fast fashion, holiday shopping along The Magnificent Mile is a group must-do. Stop in the many boutiques that line this famous stretch of North Michigan Avenue. Don’t miss more shops inside upscale malls like the 900 North Michigan Shops, The Shops at North Bridge, and Water Tower Place.
Day 2/Evening
Spend the evening wandering through Lincoln Park Zoo’s glittering ZooLights holiday displays, featuring more than 3 million lights. The nighttime experience has been a Chicago holiday staple for the past 30 years. Your group can walk through a light tunnel, ride the Ferris wheel and carousel, or learn about the zoo’s animals during an indoor tour. Themed areas offer roasted s’mores, hot cocoa, mulled wine, and more.
Or visit the Frosty’s and Santa Baby pop-up holiday bars, known for their over-the-top holiday decorations and specialty drinks with names like the Clausmo and Angry Elf Martini. Make group reservations in advance.
Day 3/Daytime
The Griffin Museum of Science and Industry gets festive with its annual Christmas Around the World and Holidays of Light exhibits. The display started with a single tree in 1942. Today, the museum’s Grand Tree stands four stories tall in the domed Rotunda, and volunteers decorate over 50 smaller trees that reflect international cultures and traditions.
Head to Gallagher Way at historic Wrigley Field (home of the Chicago Cubs baseball team) to celebrate the season. Winterland at Gallagher Way brings an ice rink, rides, and games to the site of the famed venue. Winterland also offers a variety of exciting activities, including holiday movies and crafts, pictures with Santa, and more from Thursdays to Sundays in December until Christmas.
Day 3/Evening
Take your group to see the holiday favorite Home Alone Christmas movie scored live by members of the Chicago Symphony Orchestra at Symphony Center. Home Alone in Concert will be presented at 7:30 p.m. Dec. 12, 1:30 p.m. on Dec. 13, and 3 p.m. on Dec. 14, 2025.
Or get group tickets for a fast-paced professional sports match at the United Center. Cheer for a Chicago Bulls basketball game or watch the skates fly during a hockey game featuring the Chicago Blackhawks. Visit the United Center’s Atrium to shop for team gear and take group pictures with the statue of basketball superstar Michael Jordan.
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