Winter is definitely one of the most wonderful seasons of the year in Chicago, when holiday lights are everywhere and the snow lends the city an additional sparkle.
Enjoy the season by choosing some of the many winter activities the city features, such as snowshoeing along the lake’s snowy shores, sliding down the hill, ice skating under the Bean, or visiting many photo-worthy places.
The snow season in the Windy City is the best time for strolling among Christmas lights with a mug of hot mulled wine, skating on one of the city’s various outdoor ice rinks, or snuggling in a museum café. After all, we all know that hot chocolate tastes better while wandering through snow-covered streets!
Here’s a list of some things you can do while on a winter trip in Chicago!
1. Take A Trip Around “The Loop”
The Loop is a business and tourist hub that many Chicagoans avoid due to the elevated railway’s round route around the city’s business and commercial sector. Even so, there’s a rich cultural and historical backdrop that makes exploring it worthwhile.
Visit the highest skyscraper in the city (it was actually the highest in the world until 1998) and go to the peak of it. The Sears Tower, formally known as the Willis Tower, is a 110-story building located right in the Loop community area in Chicago. Once you’re up there, you’ll get the chance to see the breathtaking panoramas of Lake Michigan and the city from the building’s Skydeck.
2. Visit A Christmas Market
We know winter is the best season to chill indoors while enjoying the warmth of your home. But what will Christmas be without a Christmas Market? If you’re planning to visit Chicago, we have good news for you! The city’s two Christmas markets, which are inspired by European customs, are excellent places to truly feel the holiday spirit throughout the colder months.
Take a walk through the heart of the city while smelling the aroma of roasting nuts and listening to Christmas songs. Don’t miss out on the baked pretzel or sausage, as well as the German specialty mulled wine, Glühwein.
Christkindlmarkts are among the best, most authentic, and only official Christmas markets in the US, so there’s no need to be concerned if you can’t make it to Germany this year.
3. Go Ice Skating At A Special Facility
One of the best parts about winter in Chicago is the multitude of lovely ice rinks that pop up all over the city. These seasonal rinks are a popular winter tradition for both locals and visitors.
If you’re about to visit Chicago this winter, you should definitely go to Millennium Park. A destination that should be on everyone’s list of stuff to do in Chicago during winter, this public park is a wonderful place where you’ll be surrounded by breathtaking views of Chicago, including the city’s famous Cloud Gate, commonly known as “The Bean”, covered in snow.
Stop for a spin on the winding Skating Ribbon in lovely Maggie Daley. This route is longer than a circuit around a regular ice skating rink, and the whole place is dotted with evergreen trees.
4. Curl With Buddies And Have Some Beverages
Take a trip to the quaint curling rink located on the deck atop the Gwen Hotel. Curling is a popular winter sport, and the iceless surface on the rooftop of the building allows guests to give it a try while sipping on a specialty cocktail. In the evenings, the rooftop terrace is lit by the fire pits, which give the whole place a cozy vibe. Relax there while enjoying the complete cuisine.
The Kaiser Tiger beer garden is another famous spot in Chicago, especially in the summer as it has bocce courts. But in the winter, the place is transformed into a curling rink. There are electric heaters to keep people warm between rounds, as well as hot cocktails to warm them up on a cold night in the beer garden.
5. Try Out Snowshoeing And Sledding
Bring your sled and get ready to have a lot of fun! The Soldier Field Sledding Hill is a parkland surrounding the old Soldier Field, and you definitely should go there if you love sledding. The 33-foot tall hill has a slope of 220 feet, so just imagine how much fun you and your friends will have there.
Even when the city doesn’t get enough natural snowfall, the Chicago Park District uses artificial snow to provide a snowy, fluffy sledding hill. There’s no better spot to enjoy a bird’s-eye view of Lake Michigan than from the peak.
You should also try snowshoeing on Northerly Island, an amazing man-made peninsula sticking outward from Lake Michigan.
6. Visit The Zoo Animals
You’d be surprised to know that the Lincoln Park Zoo is one of the best destinations to visit in Chicago during the winter. On the surface, the bitterly cold weather may seem like an odd pairing with a stroll through the Zoo, but we’d argue that those who miss out on visiting it are losing their chance to see something truly special.
During the wintertime, people will be able to see polar bears, penguins, and snow monkeys engaging in playful activities outside. There are also animal shelters that you can visit too — penguins, guinea pigs, and apes, all migrate indoors during the snowy months.
7. Take A Picture In The Snow
The early bird gets the worm… or the bean. The Millennium Park’s charm is multiplied ten times over during the winter. The Cloud Gate, commonly known as “The Bean”, is one of the most famous landmarks in Chicago; that’s why every tourist wants to snap a picture of it.
It’s quite easy to get a picture of Cloud Gate with no people around if you set your alarm and manage to be there before the whole place gets crowded. You should also take a picture of yourself on the reflected surface of the ice, and then go down the stairwell, where you’ll find a free ice skating rink.
This instant camera is a great tool to help you catch every lovely moment during your trip.
8. Visit the Indoor Gardens
Visit one of Chicago’s free-access indoor gardens to get out of the cold and warm up a little. The Lincoln Park Conservatory is a public attraction located in historic Lincoln Park that features multiple rooms packed with lots of exotic plants and flowers.
Another option would be to step out of the cold into the Garfield Park Conservatory, which hits all the senses — in the most exquisite way. Cacti stand sentry, flowers perfume the humid air, and a waterfall cascades into a lagoon.
Paths will get you through 2 acres of indoor gardens, including a room that will transport you back in time — think swamps, rocks, and ferns. It’s a beautiful (and warm) place to get lost.
9. Look At The Frozen Lake
The freezing of Lake Michigan, which creates a mesmerizing scenery, is one of the many reasons why Chicago is truly breathtaking during the winter months. Visit the Lakefront Trail for a spectacular view of the entire area and a close encounter with the skyline.
In addition, you can warm up a little before continuing your winter adventure by taking a trip to some of the city’s best retail areas (like The Magnificent Mile) and excellent museums (such as the Museum of Science and Industry, the Adler Planetarium, and the Peggy Notebaert Nature Museum).
You may also want to read 10 Epic US Winter Festivals You Shouldn’t Miss!
