A perfect family-friendly holiday weekend in Chicago: a three-day itinerary

During the holidays, Chicago sparkles with seasonal traditions both big and small, making it a magical destination for a family holiday getaway.

Families can admire glittering department store windows, celebrated theatre productions, festive Christmas markets, and dazzling holiday light displays that transform the city into a holiday wonderland.

A perfect holiday weekend in Chicago includes exploring festive attractions, skating at a scenic outdoor rink, and discovering holiday surprises around every corner. This three-day itinerary pairs classic family-friendly holiday traditions with neighborhood favorites many visitors miss.

Day one: Classic Chicago holiday magic

Highlights include:

• Holiday windows at Macy’s
• Shopping at Christkindlmarket
• The city’s official Christmas tree in Millennium Park
• Holiday traditions at the Art Institute of Chicago

Start your holiday weekend in the heart of downtown, where many of Chicago’s most cherished traditions have delighted families for generations.

Begin the morning with a stroll along State Street to admire the intricate holiday window displays at the Macy’s department store, housed in the historic Marshall Field’s building. Stop inside for a peek at the Grand Tree.

Then head to Christkindlmarket, a bustling holiday bazaar inspired by traditional German Christmas markets, where you can shop for handcrafted gifts, sip a warm mug of hot cocoa, and share a sweet treat.

Next, enjoy a walk through the Loop to Millennium Park to see the city’s official Christmas tree. Part of a century-old Chicago tradition, this year’s soaring tree stands over 50 feet tall in the heart of the park.

For lunch, check out the Loop’s kid-approved options:

• The Berghoff, one of Chicago’s oldest restaurants, serves German-American comfort food.
• The Walnut Room, a historic restaurant known for its magical holiday decor
• The Dearborn, serving tavern fare and thin crust pizza across from Christkindlmarket
• Hello Kitty Cafe, a new spot offering cute sweets and a special afternoon tea

After lunch, stop at the Art Institute of Chicago to see the enchanting Thorne Miniature Rooms. These tiny dollhouse-sized rooms will leave kids and adults alike speechless.

While you’re there, don’t miss the spectacular Neapolitan Crèche, which fills an entire gallery with hundreds of handcrafted figures depicting a nativity scene. Due to the fragility of the silk and embroidery, the display can only be on view for a few weeks every year.

For an afternoon treat, stop by the historic Palmer House Hilton for a brownie in the hotel where the iconic dessert was created for the 1893 World’s Columbian Exposition, then savor it beneath the grand lobby’s festive holiday decorations.

As evening settles over the city, stroll north along Michigan Avenue, where The Magnificent Mile twinkles with more than one million lights wrapped around trees stretching from the Chicago River to Oak Street. Browse the shops, admire the holiday windows, and soak in the glow of one of America’s most delightful holiday streets.

Day two: South Side traditions and winter wonder

Highlights include:

• Christmas exhibits at the Griffin Museum of Science and Industry
• Ice skating and lunch in Hyde Park
• A holiday show for the whole family

Kick off your day of fun at the Griffin Museum of Science and Industry, home to the annual Christmas Around the World and Holidays of Light exhibit.

Since the 1940s, this tradition has showcased dozens of trees and displays representing cultures and holiday celebrations from around the globe. Be sure to pop into the museum’s massive gift shop, where shelves are packed with science kits, model trains, engineering toys, space-themed gifts, and unique stocking stuffers.

Head to the Gothic, ivy-covered campus of the University of Chicago, where you’ll find the scenic Midway Plaisance ice rink. Admission is free, and skate rentals are available for children and adults. The rink is open from November through February.

Enjoy lunch at Café Medici, a longtime Hyde Park gathering place tucked just off the University of Chicago campus.

At nearby 57th Street Books, one of Chicago’s best independent bookstores, you can browse a fine selection of colorful children’s picture books.

In the evening, get tickets to see a classic holiday show. Chicago’s stages are filled with mesmerizing productions all winter long, including:

• A Christmas Carol at the Goodman Theatre
• The Nutcracker by Joffrey Ballet at Lyric Opera House
• The Beatrix Potter Holiday Party at Chicago Children’s Theatre
• It’s a Wonderful Life: Live in Chicago! at American Blues Theater
• Hershel and the Hanukkah Goblins by Strawdog Theatre Company

Day three: Winter flowers and holiday lights

Highlights include:

• Holiday magic at a winter wonderland
• Winter Flower Show at Lincoln Park Conservatory
• ZooLights at Lincoln Park Zoo

Start your day outside Wrigley Field at Winterland at Gallagher Way. This family-friendly outdoor festival offers free admission. Rent skates and twirl around the ice rink, meet Santa at his workshop, or browse the miniature version of Christkindlmarket.

Next, head to the Lincoln Park Conservatory. The annual Winter Flower Show will be in full bloom, filling the glass-enclosed building with fragrant greenery and bright red poinsettias. It’s the perfect spot to warm up and be surrounded by natural beauty.

After your conservatory visit, enjoy lunch at R.J. Grunts, a longtime Lincoln Park favorite known for its burgers, hand-spun milkshakes, and giant salad bar.

As dusk falls, make your way to Lincoln Park Zoo for ZooLights, where millions of sparkling lights illuminate the zoo grounds, creating one of Chicago’s most magical holiday settings.

For a farewell dinner, head to the historic Old Town neighborhood and settle in at Topo Gigio for family-friendly Italian favorites or The Fireplace Inn, where a crackling hearth creates a warm and welcoming setting on a winter evening.

Before heading home, stop at The Fudge Pot, an Old Town institution since 1963, where kids can watch chocolatiers at work and choose from chocolate-covered pretzels, hand-dipped chocolates, and house-made fudge. It’s the perfect place to pick up a sweet treat for the ride home and a few stocking stuffers to remember your Chicago holiday adventure.