Why Chicago Might Be the Most Magical City at Christmas

Chicago has it all at Christmas: magical twinkling lights along Michigan Avenue, steaming mugs of glühwein at Christkindlmarket, and ice rinks with skyline views. As lifelong Chicago residents (and insatiable Christmas fans), these are the ways my family celebrates Chicago in Chicago.

Bundle up and get ready to celebrate the season!

1. Chicago’s Christmas Tree

The city’s Christmas tree stands in Millennium Park, just waiting for visitors to come by and take a beautiful nighttime selfie, organize the kids for a Christmas card photo or simply stand and marvel at the beautiful lights.

Chicago’s official Christmas Tree will be illuminated on November 21 at 6 p.m. near the intersection of Michigan Avenue and Washington Street. It stays lit into early January, offering a warm, magical backdrop for winter strolls.

SheBuysTravel Tip: It can be cold walking around the Loop at night in December. Book a room at the Fairmont Hotel across the street from Millennium Park. That makes it easy to go back and warm up when you need a break, or to tuck into one of the Fairmont’s comfy beds for a long night’s slumber at the end of the evening.

2. The Magnificent Mile Lights Festival and Parade

The annual Wintrust Magnificent Mile Lights Festival is the official kick-off of Christmas in Chicago. The highlight is a spectacular parade down North Michigan Avenue with fabulous floats, giant helium balloons, marching bands from across the country, popular celebrities, musical performances, and, of course, Santa Claus on Wintrust’s grand finale float,

As the parade makes its way down the Magnificent Mile (that’s Chicago’s premier shopping district), it turns on the Christmas lights along the way, block by block. It’s a magical experience, followed by a fireworks spectacular over the Chicago River.

Led by Grand Marshals Mickey and Minnie Mouse, the 2025 parade steps off at 5:30pm from Oak Street and travels south on Michigan Avenue, with fireworks over the Chicago River starting around 7:15.

SheBuysTravel Tip: Stay at a hotel on the Magnificent Mile and you might even be able to watch the parade from the comfort (and warmth) of your room. My favorite Mag Mile hotel is the InterContinental Chicago. The Chicago Marriott Downtown is another great option.

3. Take a Holiday Cruise

This section is sponsored by City Cruises.

It’s one thing to walk around the city admiring the millions of twinkling lights. But it’s a special experience to celebrate the holidays on the water.

City Cruises offers a host of special holiday-themed cruises where you can enjoy a meal and entertainment while cruising Lake Michigan with views of Chicago’s magnificent skyline. Even better, you can do it all from the warmth of the boat’s indoor spaces – or the open-air decks if you prefer. Choose Lake Michigan cruises or “Premier Plus” luxury cruises on the Chicago River.

Here’s a taste of the cruises offered this year:

• Thanksgiving Cruise: Booking the lunch cruise means you don’t have to cook or wash dishes, just enjoy your loved ones and the city sights. 
• Christmas Cruises: Choose from Christmas Eve and Christmas Day dinner cruises.
• New Year’s Eve and New Year’s Day Cruises: Ring in the new year on the water with dinner, drinks and dancing.

SheBuysTravel Tip: The holidays are magical in Chicago, so they draw a crowd. Book your holiday cruise early – they sell out fast! Book your City Experiences holiday cruise by November 9 and use code HOLIDAY50 to get 50% off your second ticket for Thanksgiving, Christmas, or New Year’s Eve sailings!

4. ZooLights at Lincoln Park Zoo

ZooLights at Lincoln Park Zoo is an absolute, no-doubt-about-it, must-do during Christmas in Chicago, The charming Lincoln Park Zoo dresses up for the holiday with 3 million lights from November 21, 2025–January 4, 2026.

This is a ticketed event ($7-20 per person; free on select Mondays) that supports the zoo’s world-class animal care, global conservation efforts, and innovative learning programs.

This is one of my absolute favorite Christmas events in Chicago. It feels as though even the animals are excited about Christmas as you walk among the giant 3D light displays, musical light shows, ice carvings and strolling carolers.

SheBuysTravel: My favorite hotel close to the zoo is the boutique Hotel Zachary near Wrigley Field, the home of the Chicago Cubs. It’s an Uber ride away, but well worth it.

5. Christkindlmarket Chicago

A holiday tradition since 1996, Christkindlmarket attracts vendors from all over the world who come to Chicago to sell German-inspired food, hot chocolate and one-of-a-kind holiday gifts. From handmade items like knit hats and cuckoo clocks to foods like strudel and sausage, the sights and smells of the Christmas market are the stuff that Christmas dreams are made of.

Held November 21 through Christmas Eve at Daley Plaza, Christkindlmarket is rich in warm German tradition and flair. It is very crowded and busy here, especially in the evenings, so this may not be the best activity for little ones.

Read More: Best Chicago hotels for families.

6. See a Christmas-Themed Show

Our two annual favorites:

• A Christmas Carol at the Goodman Theater. This classic retelling of the ghosts of Christmas past, present and future can be a little dark, so may be too scary for little ones. This year’s performances run from Nov. 15 through New Year’s Eve.
• The Nutcracker presented by the incomparable Joffrey Ballet at the Lyric Opera House. Another classic show, expect the audience to include lots of little girls dressed up in their ballerina finest, Shows are Dec. 5-28.

Chicago is home to a plethora of world-class theater, arts and music. From Cirque du Soleil’s “Twas the Night Before” to “Elf, the Musical,” holiday-themed performances abound.

SheBuysTravel Tip: I always like to be close to my hotel at the end of a long day and late night of having fun. The show you choose should determine the hotel you choose. If you are going to the Goodman, for example, stay at Royal Sonesta Chicago Downtown. If you’re going to the Nutcracker, stay at the Hyatt Place Chicago Loop.

7. Ice Skating with a Skyline View

Ice skating is one of the best ways to stay warm in Chicago in the winter, The big rink is the McCormick Tribune rink at Millennium Park, just below the Bean. There’s also skating at Maggie Daley Park, just across the BP Bridge. There, it’s a skating ribbon that snakes around the climbing walls.

Skating is free if you bring your own skates. Rentals are available at both locations.

Read More: Review of theWit Chicago Hotel:: Fab River Views in the Windy City

8. Christmas Around the World at theGriffin Museum of Science and Industry

Seeing the Christmas trees from around the world is one of my earliest memories of Christmas in Chicago. My parents took my brother and me every year.

At the holidays, Christmas Around the World and Holidays of Light Exhibit (running November 8, 2025 January 6, 2026) transforms the museum’s giant rotunda into a forest of perfectly decorated Christmas trees. With the 45-foot Grand Tree in the center, more than 50 trees and holiday displays represent different cultures and traditions from around the globe.

The museum (my favorite of all of Chicago’s world-class museums) is in Hyde Park, about seven miles south of the Loop. While there are hotels in that charming neighborhood, which is also home to the University of Chicago, I recommend heading back downtown for the night.

9. The Great Tree at Macy’s Walnut Room

Visiting Macy’s on State Street is one of my favorite Christmas memories. Each year, my mom, aunts and girl cousins would start by admiring the gigantic holiday window displays outside of Macy’s (then called Marshall Field) before making our way into the department store to dine in the historic Walnut Room adorned by a giant 60-foot Christmas tree.

SheBuysTravel Tip: Make reservations before your visit or risk waiting in line for three hours or more on the day of your visit. 

10. Shop Til You’ve Checked Everyone Off Your Holiday List

What is more festive than holiday shopping? Chicago’s Magnificent Mile, the city’s premier shopping district, is the place to find high-end shops like Gucci, Bloomingdale’s, Burberry and Neiman Marcus. It’s the Midwest’s equivalent to Beverly Hills’ Rodeo Drive or New York’s 5th Avenue!.Kid-friendly stops include American Girl Place.

Neighborhoods like Lincoln Square, Andersonville and Bucktown offer boutique finds for a truly one-of-a-kind gift.

11. Ride the CTA Holiday Train and Bus

Each year, the Chicago Transit Authority decks the halls of a train and a bus and sends it out to surprise riders.

On the train, Santa waves to riders from his sleigh on an open-air flatcar carrying his reindeer and decorated holiday trees. Each train car is wrapped with holiday images and thousands of twinkling lights.

The 60-foot Holiday Bus plays Christmas music and Santa Claus yells a jolly “Ho-ho-ho!” from the roof hatch.

Both the train and the bus run on a schedule you can find here.

Where to Celebrate Christmas in the Suburbs

Each of the following is at least a 30-minute drive from the city. While you could take public transit (the train system in Chicago is robust and reliable), you still need an Uber to get to your final destination. It’s easiest to drive to these Christmas attractions.

12. Holiday Magic at Brookfield Zoo

Brookfield is the bigger Chicago area zoo, located in the southwest suburb of Brookfield. At Christmas, the zoo shines with 2 miles of lights, a 41-foot-tall Christmas tree, a 600-foot Tunnel of Lights, an ice skating rink and a scavenger hunt to find the hidden gnomes.

Some of the animal houses are open during the Holiday Magic lights festival. That makes it easy to duck inside and warm up. The festival begins on November 21, 2025 and runs on select nights through January 4, 2026.

13. Lightscape at Chicago Botanic Gardens

This dazzling Christmas light show replaces Wonderland Express, which delighted my family for years. But the new show, complete with singing trees, is a feast for the eyes. It runs November 14, 2025 through January 4, 2026.

The Chicago Botanic Garden is in north suburban Glencoe.

14. Illumination: Tree Lights at The Morton Arboretum

The 50 acres of the Arboretum are transformed into a spectacle of color, light and sound, including 150 colorful lanterns. Walk along a one-mile paved path to hear festive music and see the thousands of lights. Stop along the way to warm up by a fire and roast marshmallows for s’mores, or stop in one of the concession tents for a snack and beverage. It runs November 13, 2025 through January 3, 2026.

The Morton Arboretum is located in the western suburb of Lisle.

15. Drive-Thru Christmas Lights in Chicago

If you don’t like the cold, Light of Christmas is for you! It happens at Rate Field, home of Chicago’s South Side baseball team, the White Sox. It runs from November 20, 2025 through January 7, 2026. This enchanting experience features more than 1 million synchronized lights that you can enjoy from the warmth of your own vehicle. Prices range from $23.49-$54.99 per car, and the hours are 5-9pm.