A Holly Jolly Guide to Chicago During the Holidays

“With such a diverse population from all over the world, you can find so much to celebrate during the holiday season. 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 even invented in the city back in 1939 by Montgomery Ward (a former department store).

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

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 ways to enjoy the festive season. Sheehy suggests advance ticket purchases, explaining that: “This event is extremely popular and sells out quickly, so if you would like to partake, 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 “decorations spill out of every conceivable corner of the premises. This event does require purchasing an entry ticket, but the lowest-price admission ticket also includes a drink with purchase,” Sheehy said.

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 decorations and will also simultaneously give you that authentic Chicago feeling, especially if you try their original Christmas in Your Mouth shot.”

But the most important place to visit for Chicago’s festive eats? Sheehy advises heading to the Christkindlmarkt (there are three different locations) to sample everything from schnitzel and pretzels to potato pancakes and hot spiced wine.

The aforementioned Christkindlmarkt is the ideal place for festive foods as well as purchasing festive souvenirs, such as ornaments, holiday decor, and other handmade gifts.

Sheehy also advises picking up a festive souvenir mug at the 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 in all its holiday grandeur, stopping in 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 window displays, pick up a box of their famous Frango Chocolate Mints.”

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 Christmas decorations are a treat for any Chicago visitor … or even local.

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 located along the Chicago River. The London House is also a Chicago favorite with unbeatable views overlooking the Chicago River,” she suggests.

Walking along Chicago’s Magnificent Mile and State Street to admire the holiday decorations is sure to get visitors 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 glittering lights. A favorite of Sheehy’s, it offers “ice skating, 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 provide a jolly experience for guests of all ages,” she says.

She also provides some arrival advice. “The easiest way to get to Jack Frost from The Loop or the Magnificent Mile is to take a taxi or rideshare. You can also 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 should also head to the famous Millennium Park. “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 ribbon. It’s like a frozen lazy river in the heart of Chicago."