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A Holly Jolly Guide To Chicago During the Holidays

Tour guide Brooke Sheehy explains why Christmas in Chicago is one of the best times to visit the Windy City.

Hi, I'm Lori!

Lori Zaino is a bilingual, Madrid-based freelance writer and editor with bylines in CNN, NBC, Business Insider, and The Points Guy. An avid traveler, she’s visited more than 60 countries—and has written about most of them.

There’s a wealth of Christmas things to do in Chicago during the holiday season, according to Windy City-based tour guide Brooke Sheehy, who says the Illinois hub “has so many holiday traditions, some dating back to the late 1800s.”

After getting a BFA in acting from the Chicago College of Performing Arts at Roosevelt University, Sheehy traveled around Southeast Asia and Australia. Three years ago, she moved back to Chicago and began leading tours, discovering her love for food tours in particular.

Now, she guides the Holiday Hike Tour, where she helps visitors explore Chicago’s food culture, twinkling lights, and holiday traditions. Here, expect to sample Chicago specialties such as deep-dish pizza, Chicago’s famous hot dogs, Italian beef, brownies, and hot apple cider, before wrapping up at the city’s beloved Christkindlmarkt. This tour is a must for those seeking festive things to do in Chicago at Christmas.

What makes Chicago great for the holidays

Brooke, pictured, has led this festive tour in Chicago for several years.
Brooke has led this festive tour for several years.Foto: Brooke Sheehy

You’ll be blown away by the Windy City at Christmas.

“With such a diverse population from all over the world, you can find so much to celebrate during Christmas in Chicago. I love learning about more of the traditions here in the city and then sharing the spirit of the season with each guest on my tour,” Sheehy says.

It turns out Chicago’s holiday cheer dates back quite a while—Rudolph the Red-Nosed Reindeer was invented in the city back in 1939 by one of Montgomery Ward’s (a former department store) copywriters who was asked to create a Christmas story as a seasonal promo.

And the city remains joyful and bright today thanks to plenty of Chicago Christmas decorations, according to Sheehy. “Lincoln Park Zoo hosts a free display of over one million twinkling lights, the Museum of Science and Industry decorates Christmas trees in the styles of over 50 cultures, and the Joffrey Ballet presents the Nutcracker.”

Where to try Chicago’s top holiday sips and snacks

The Chicago Christkindlmarkt is one of the best spots for festive food.
The Chicago Christkindlmarkt is one of the best Chicago Christmas markets for festive food.Foto: EQRoy / Shutterstock

Discover Chicago’s famous food, seasonal-style.

While the Holiday Hike guides you through some of Chicago’s most quintessential foods, visiting Macy’s Walnut Room for Christmas Tea is one of the most popular things to do in Chicago at Christmas. Sheehy suggests buying advance tickets, explaining that, “This event is extremely popular and sells out quickly, so if you would like to go, mark your calendar for the day when tickets go on sale.”

For something a little less highbrow, consider Frosty’s Christmas Bar near the North/Clybourn CTA Red Line stop, where, according to Sheehy, “Decorations spill out of every conceivable corner of the premises.” Adding, “This event does require purchasing an entry ticket, but the lowest-price admission ticket also includes a drink with purchase.”

She also recommends checking out Butch McGuire’s. “This Irish pub located off of the Clark/Division CTA Red Line has a full menu, a full bar, and is full of holiday cheer! They never skimp on the holiday displays and will also simultaneously give you that authentic Chicago feeling, especially if you try their original ‘Christmas in Your Mouth’ shot.”

But, according to Sheehy, the most important place to visit for Christmas dining in Chicago is Christkindlmarkt (there are three different locations) to sample everything from schnitzel and pretzels to potato pancakes and hot spiced wine.

Where to go Christmas shopping in Chicago

Do some seasonal shopping at Macy's on State Street in Chicago.
Do some seasonal shopping at Macy's on State Street.Foto: Nagel Photography / Shutterstock

Surprise your friends and family with the best gifts.

The aforementioned Christkindlmarkt—a favorite among Chicago holiday markets—is the ideal place to try festive foods and buy souvenirs such as ornaments, holiday decor, and other handmade gifts.

Sheehy also advises picking up a festive souvenir mug at this Chicago Christmas market. “Purchase them with an order of hot chocolate, hot apple cider, or mulled wine. With three different holiday classics and two distinct mug designs, you’re sure to find something to gratify the entire family.”

Shoppers should also stroll the Magnificent Mile Lights Festival—one of the biggest Christmas events in Chicago—and stop by some big-name retailers. “The most iconic store around the holidays is Macy’s on State Street. Since you’re already planning on going there for the architecture and holiday displays, pick up a box of their famous Frango Chocolate Mints.”

Where to stay in Chicago this Christmas

The historic Palmer House Hotel is a particularly Christmassy option.
The historic Palmer House Hotel is a particularly Christmassy option.Foto: Bobby's Bike Hike

Keep warm out of the winter winds.

One of Chicago’s most famous institutions is the Palmer House Hotel. Originally built in 1871, the hotel was destroyed just a couple of weeks later in the Great Chicago Fire. Rebuilt in 1875, the hotel’s long history and beloved Chicago Christmas decorations are a treat for visitors and locals alike.

The hotel is also a favorite of Sheehy’s. “The Palmer House Hotel located in the Loop is my top choice to stay in the city. Its lobby is decked out with a giant [Christmas] tree and many gorgeous decorations.”

Another option to consider is the London House Hotel on the Chicago River. The London House is also a Chicago favorite with unbeatable views overlooking the Chicago River,” she suggests.

Top holiday activities in Chicago

Go to the ice skating rink by the Bean this Christmas in Chicago.
Go to the ice skating rink by the Bean this Christmas in Chicago.Foto: Radoslaw Lecyk / Shutterstock

Feel jingle-bell jolly in the Windy City.

Chicago’s most festive attractions and activities include walking along Chicago’s Magnificent Mile on Michigan Avenue, and State Street. Here, visitors can admire the Christmas lights in Chicago which will put everyone in your party in the holiday spirit. Sheehy advises bundling up with layers, though, as Chicago winters are no joke.

Another seasonal activity is the Jack Front Winter Pop-Up, home to 10,000 twinkling lights. A favorite of Sheehy’s, it offers “ice skating rinks, bumper cars, winter tubing, and all the Instagram-worthy photos your heart could possibly desire. It also has a full bar to sweeten the ticket price and is one of the best things to do in Chicago at Christmas for guests of all ages,” she says.

She also provides some insider intel. “The easiest way to get to Jack Frost from The Loop or the Magnificent Mile is to take a taxi or rideshare. Or you can travel like a local and take the CTA Red Line to North/Clybourne and then take a leisurely 15-minute walk to the event space.”

Fans of ice skating rinks should also plan to visit the famous Millennium Park—an absolute must when it comes to experiencing Christmas in Chicago. “Go for a spin on the ice rink under the majestic gaze of the Bean. Or, cross over the futuristic bridge from Millennium Park to Maggie Daley Park to skate the ice skating ribbon. It’s like a frozen lazy river in the heart of Chicago."

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