Chicago is one of my favorite American cities; even when winter is coming. Nicknamed the ‘Windy City’ for a reason, Chicago can dish out some pretty frosty weather, making even the local pigeons gather around fires just to keep warm. The famous Chicago River turns to ice. And the beloved Chicago Bean gets completely snow-capped. Despite its freezing temperatures, this already vibrant city seems to come to life even more during the winter holidays, and this guide will help you keep your mind off the cold and focused on enjoying the festivities.
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The Millennium Park Ice Skating Rink
Attracting over 100,000 ice skaters each year, the McCormick Tribune Ice Rink at Millennium Park is a great place to hang out, whether you want to show off your ice skating skills or simply enjoy the scenery.
Location: Millennium Park, McCormick Tribune Ice Rink, 201 E. Randolph St., Chicago, IL 60601 (view map)
Cost: Admission is FREE. Skate rental is $12.
The Cloud Gate AKA ‘ The Chicago Bean’
Looming right over the skating rink is one of Chicago’s most unique and interesting sculptures. It reflects Chicago’s magnificent skyline, and when the snow is falling, the Bean transforms into a giant snow globe. Be sure to snap a few photos of yourself with The Bean before heading off to your next destination.
Cost: FREE and available for your viewing pleasure year-round.
Location: Millennium Park, 201 E Randolph St, Chicago, IL 60601 (view map)
Christmas Around the World and Holidays of Light
Every year, The Museum of Science and Industry displays their annual exhibit “Christmas Around the World and Holidays of Light.” It features over 50 trees and displays, festively decorated by volunteers from Chicago’s ethnic communities to reflect their diverse culture and holiday traditions. Experience Christmas customs from all over the globe!
Cost: Included in museum admission
Location: 5700 S. Lake Shore Drive, Chicago, IL 60637 (view map)
Christkindlmarket Chicago
Now if you really want something festive to get into, make sure you visit the Chriskindlemarket at Dearborne and Washington St. This open-air Christmas festival, held every year in Chicago’s Daley Plaza, was inspired by the Christkindlesmarkt in Nuremberg, Germany. It brings the local charm of a cherished German tradition right to Chicago’s doorstep. Christkindlmarket Chicago has grown to become the largest open-air Christmas festival and one of the most popular winter attractions in the heart of the city. Get in the spirit of the holidays as you walk around the market, enjoying delicious traditional German food, and of course, drinks!
Cost: Admission is FREE. Bring cash for vendors.
Location: Daley Plaza, 50 W Washington St, Chicago, IL 60602 (view map)
Magnolia Bakery
About a block away from the Christkindlemarket, you can go warm up inside Magnolia Bakery, a charming and cozy dessert shop filled with holiday delicacies. Famous thanks to TV shows and movies like Sex and the City and The Devil Wears Prada, this bakery has turned into a pop culture icon. Be sure to try out Magnolia Bakery’s Famous Banana Pudding, a customer favorite.
Cost: View menu here
Location: 108 N. State St (Block 37), Chicago, IL, 60602 (view map)
Wildberry Pancakes and Cafe
If you’re on the hunt for a good brunch spot, I recommend Wildberry Pancakes and Cafe. Their holiday-themed menu options will make you melt.
Eat: The Eggnog French Toast is a nice holiday treat and the sprinkles they add on top are a nice festive addition.
Drink: The S’mores Latte and the White Hot Chocolate are just what the doctor ordered to warm you up after walking a few blocks in the Windy City.
Location: 130 E. Randolph St, Chicago, IL 60601 (view map)
Garrett Popcorn Shops
No matter what time of year you visit Chicago, you can’t leave without trying any of the foods this city is famous for: hotdogs, deep dish pizza, and Garrett Popcorn. If you visit a Garrett Popcorn Shop, there will probably be a line out the door. A patron of 30 years I interviewed described this popcorn as “the absolute best and extremely addictive.” If you’re feeling generous, you can purchase one of their tasty holiday bundles to give away as a Christmas gift!
Eat: The Holiday Mix. Their website describes this concoction as “smooth and creamy white chocolate covered CaramelCrisp® gently stirred with fresh Gingerbread CaramelCrisp®“ –sounds like a perfect holiday mix!
Location: Multiple locations in Chicago (view all locations on map)
The Magnificent Mile
If you need to do some holiday shopping in Chi-town, The Magnificent Mile is the place to be. The shops here are as diverse as the products they sell and cater to all kinds of budgets. You’ll find clothes, shoes, jewelry, cosmetics, art, electronics, home furnishings, and even pet boutiques. Venture over to The Magnificent Mile to find a Christmas gift for every person (or pet) in your life.
Location: N Michigan Avenue (view map)
The Signature Lounge
Visit the John Hancock Center at nighttime and take the elevator all the way up to the 96th floor, where you’ll enter the Signature Lounge. Here, you can enjoy a bird’s eye view of Chicago lit up for the holidays. While you’re up there, you can also dine on fine cuisine or just relax with one of their signature cocktails. Either way, you’re guaranteed to enjoy an amazing view of this stunning city.
Cost: The elevator ride is FREE.
Location: 875 N. Michigan Ave, Chicago, IL 60611 (view map)
Palmer House Hilton
Before you secure your accommodations, do your research and make sure you book a hotel that’s conveniently located near many of your planned activities. I recommend downtown Chicago’s Palmer House Hilton. As soon as I arrived here, I was immediately ready to celebrate the holidays! The hotel’s Christmas decorations were classy, festive, and made me feel right at home. Best of all, the location is perfect for exploring the city. Most of the attractions I’ve listed here are within walking distance of the Palmer House; after layering up for the cold weather, we were able to do most of our sightseeing on foot!
Cost: Get special offers and rates here
Location: 17 East Monroe St, Chicago, IL 60603 (view map)
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