The ultimate Chicago holiday itinerary: three days of festive fun

Chicago goes all out for the holidays, with something magical happening in every corner of the city. The season kicks off with the Christmas Tree Lighting Ceremony (a tradition for over a century) and things stay festive through the city’s spectacular New Year’s Eve celebrations.

Visitors can expect charming holiday markets, trees covered in twinkling lights, tons of fun seasonal events, and even a decked-out holiday train led by Santa and his elves that soars through the city.

If you’re looking for the perfect holiday getaway, this itinerary hits some of the classic Chicago experiences (like ice skating in the shadow of The Bean and shopping at a downtown Christmas market) along with a few off-the-beaten-path finds in Chicago’s welcoming neighborhoods.

Day one: classic Chicago holiday traditions

Top experiences:

• Art Institute of Chicago
• City of Chicago Christmas Tree
• Christkindlmarket
• Macy’s on State Street
• A holiday show (A Christmas Carol, The Nutcracker)

This is a packed day of top holiday sights, so bundle up and get ready for a magical start to your Chicago visit.

Start your day at the Art Institute of Chicago, the city’s world-class art museum. Spend some time wandering the museum’s many galleries, filled with priceless works and some of the world’s most famous paintings. The Impressionism gallery is particularly impressive. If you’re looking for the greatest hits, this guide tells you what to see in an hour.

Insider tip: Head to the museum entrance on Michigan Avenue to see the iconic bronze lions adorned with giant Christmas wreaths.

When you leave the museum, walk north up Michigan Avenue until you see the giant Christmas tree standing tall in Millennium Park. The massive tree shines brightly from mid-November through early January. Snap a photo, then walk a bit into the park to say hello to “The Bean” dusted in snow.

Insider tip: There’s skating in your schedule for tomorrow, but the Millennium Park ice rink and the unique Skating Ribbon are both nearby if you’re looking for more time on the ice.

Next, walk a few blocks west to Christkindlmarket Chicago. One of the city’s most beloved holiday traditions, Christkindlmarket is a bustling outdoor bazaar in the style of an authentic Christmas market. Grab a souvenir mug of hot cocoa or mulled wine and wander the booths of sweets, German treats, and handcrafted gifts.

If you have time, pop into the landmark Macy’s on State Street to see the Great Tree inside the Walnut Room.

End the night at a festive holiday show. Get tickets to A Christmas Carol at the Goodman Theatre, a heartwarming classic that’s become a tradition for generations of Chicagoans. Or see a uniquely Chicago spin on The Nutcracker, performed by the Joffrey Ballet at the stunning Lyric Opera House.

Day two: unique traditions on the South Side

Top experiences:

• Museum of Science and Industry
• Midway Plaisance ice rink
• Shopping and dining in Hyde Park

Begin your day at the Griffin Museum of Science and Industry, the largest science museum in the Western Hemisphere.

Alongside hands-on and interactive exhibits, the museum also hosts its annual Christmas Around the World and Holidays of Light. This fun seasonal showcase delves into holiday traditions from around the world with more than 50 decorated trees.

Next, lace up your skates and take a spin at the ice rink of the Midway Plaisance. This scenic spot is set against the dramatic backdrop of the University of Chicago campus.

Spend some time shopping and dining in the heart of Hyde Park. Browse for gifts at unique local businesses like design-focused The Silver Room, the carefully curated Call and Response Books, and mother-daughter-owned Suuri Designs.

Finally, find a warm spot to enjoy dinner and drinks. The award-winning Virtue is an excellent option, with warm Southern flavors and a welcoming atmosphere. Or grab a spot at the bar inside the Sophy Hyde Park, where a large fireplace keeps the vibe cozy.

Day three: rooftop curling and twinkling lights

Top experiences:

• Garfield Park Conservatory
• Curl & Chill at The Gwen
• ZooLights

In the morning, head to the Garfield Park Conservatory. The third-largest garden under glass in the world, the conservatory’s indoor gardens are the perfect serene escape from the hustle and bustle. Take time to admire the annual Winter Flower Show, when the soaring space is filled with festive plants and flowers.

Next, enjoy some friendly competition with a fun winter sport. Each winter, The Gwen Hotel in River North hosts a popular rooftop curling experience on its outdoor terrace. Enjoy seasonal cocktails and a curated menu, try your hand at curling, and warm up at the firepit table.

Afterward, spend some time holiday shopping along The Magnificent Mile, one of the world’s most iconic retail destinations. Admire the winter window displays, pop into stores, and stock up on unique gifts for loved ones (and yourself).

Finally, end your holiday weekend in Chicago with a local favorite — ZooLights at Lincoln Park Zoo. This evening event transforms the historic zoo into a true winter wonderland, with millions of twinkling lights on almost every surface. There will also be live entertainment, festive treats, and, of course, plenty of wildlife to meet. It’s a magical event, and the perfect way to wrap up your holiday weekend in Chicago.