10 Things to Do in Chicago in Winter

Chicago is one of the cities with the coldest temperatures in the U.S. Therefore, here are a series of plans that will guarantee fun and comfort on this date.

Keyvis Montilva

Keyvis Montilva

9 min read

10 Things to Do in Chicago in Winter

Chicago in Winter | ©Sean Santry

When thinking about plans in Chicago, plans abound during all times of the year. Winter in this city is quite spectacular, with frequent snowfalls and a couple of celebrations that take place in style thanks to the festive nature of its inhabitants.

Here are all the activities I've compiled in a list so you can enjoy every second of your trip to the windy city during the winter months.

1. Make sure you have a night of sporting fun

At a Chicago Blackhawks game| ©Michael
At a Chicago Blackhawks game| ©Michael

The North American Hockey League season and the NBA regular season extend into the winter months. In turn, Chicago's United Center is home to the Chicago Blackhawks and the Chicago Bulls, two of the top teams within their respective sectors of the industry, so I assure you that attending a game of either team can be an extremely fun experience. In addition, both sports are easy to follow, even for non-fans.

Plus, it's a fun way to take a break from the cold winter temperatures that define the season. Attending a venue as modern and as large as the United Center is also a once-in-a-lifetime experience for many people because of all the food you can enjoy, while sipping a beer, enjoying a very American tradition.

Book your ticket for a Chicago Bulls game

2. Visit Chicago's most famous crime scene on Valentine's Day itself

Gangsters and Ghosts Tour| ©GTE
Gangsters and Ghosts Tour| ©GTE

On February 14, 1929, on a cold winter day, one of the most important massacres in the history of the American Mafia took place. It was motivated by confrontations between Al Capone's group against some members of the North Side Gang.

Many historians credit it with being one of the triggers that led to the prosecution of Al Capone as the biggest local mob leader. So its historical significance makes a visit to this corner of the city where the crime occurred an excellent plan for those who have followed the history of this mob figure.

It doesn't hurt to find out if Chicago tourist attraction passes offer any kind of discount for the Mafia Museum on Valentine's Day. Simply because this historic event is so closely associated with the city's tourism industry. There is also a mafia and crime tour of Chicago to learn more stories about the influence these underground organizations had on the city.

Book a mafia and crime tour of Chicago

3. Celebrate New Years Eve as the locals do

Fireworks at Navy Pier| ©Abraham J
Fireworks at Navy Pier| ©Abraham J

There are plenty of ways to celebrate the arrival of New Year's Eve in Chicago if you're in town during this time. Hotels often offer themed dinners and clearly the more commercial restaurants also have a special itinerary for such an important moment of the winter season as this.

However, there are certain traditions that locals follow to give a much more proper sense of the New Year's Eve without having to adapt to the conditions of a fancy dinner or an overpriced event.

Navy Pier and the Riverwalk are two corners of the city that fill up waiting for the fireworks that are detonated at midnight over the Chicago Bay, on Lake Michigan. Therefore, I advise you to approach these areas if you are looking for a plan that is quite similar to the one experienced in New York's Times Square.

Welcome the new year flying over Chicago by helicopter

On the other hand, if you are really interested in participating in something unique and budget constraints are not a problem for you, then you can choose to celebrate the first of January with one of the best helicopter tours in Chicago. This is the perfect way to welcome the new year in style, enjoying panoramic views of a city as big and modern as this one.

Book a helicopter tour in Chicago

4. Take a stroll along the frozen shores of Lake Michigan

On Frozen Lake Michigan| ©Allan Henderson
On Frozen Lake Michigan| ©Allan Henderson

Almost every city in the world has a space that has marked the configuration of its urbanism and that in a certain way is an iconic point of this community. In Chicago it is Lake Michigan and during the winter all its shores are frozen, offering its inhabitants a quite unique landscape that is worthy of being admired by any tourist who knows how to appreciate the beauty of its surroundings.

Several points of the city are very appropriate for you to propose a walk that allows you to enjoy the winter panorama, while you know a tourist and important area of Chicago. Concrete Beach, Navy Pier and the entire Museum Campus area. It is worth mentioning that in the Museum Campus you will also find the Field Museum of Natural History and the Adler Planetarium, two spaces dedicated to culture and history that are worth visiting.

On the other hand, Chinatown and Greektown are two immigrant neighborhoods that are relatively close to this public park area. Therefore, it is also a good idea to take part in one of the Chinatown food tours that focus on this type of food if you get an appetite after walking several miles of coastline.

Reserve your ticket to the Field Museum of Natural History

5. If you are in St Patricks Day you must go to the Riverwalk area

St Patricks Day in Chicago| ©Natasha Jelezkina
St Patricks Day in Chicago| ©Natasha Jelezkina

The winter season closes with one of the most representative events of this city, St. Patrick's Day. This date is very important because it is related to the Irish migrants, which is one of the cultural pillars of the city.

At the same time, the fact that every year green paint is added on the waters of the Chicago River, makes it an activity of great interest for tourists.

Many cruises in Chicago will be sailing some of the stretches of the river during this day with special modalities in which they will offer passengers meals of Irish cuisine along with a wide variety of craft beers. Although if you go as a spectator from the shores you can also have fun attending the Parade that takes place along the Magnificent Mile or entering some of the Irish bars in the area.

Book a cruise on Lake Michigan

6. Don't miss a play or musical event.

Carol Christmas at the Goodman Theater| ©Mary Warren
Carol Christmas at the Goodman Theater| ©Mary Warren

The winter season is a busy time for Chicago's theatre and musical scene, as it is an ideal plan to escape the cold weather that characterizes these early months of the year. The Chicago Theatre usually has at least 2 shows with dates for the entire season and the occasional special concert on weekends.

The Chicago Symphony Orchestra'swinter concerts are another cultural event of the winter season that you should not miss, at least if you enjoy this type of music regularly.

Another ideal theatrical proposal is to enjoy the performance of Shakespeare in Chicago at The Lounge, located in Chicago's Loop district, one of the most recognized in the city.

7. Party on Presidents Day

Night Tour Bus| ©Alanscottwalker
Night Tour Bus| ©Alanscottwalker

Holidays are not common in the United States and when there are any they agree to coincide specifically on a Monday, just as happens with Presidents Day. This way you can enjoy a long weekend full of parties and fun.

Wicker Park, Old Town and River North are some of the neighborhoods where the nightlife is more interesting during this weekend that precedes the third Monday of February.

In turn, if you are looking for a good plan to tour the city comfortably on this holiday, do not hesitate to book the Chicago sightseeing bus. It is an ideal day, as there is hardly any traffic because many families have gone to the outskirts of the city to take advantage of this small vacation.

Book the Chicago sightseeing bus

8. Visit the Polar Animals at Lincoln Park Zoo

Zoolights at the Zoo| ©Robby Gragg
Zoolights at the Zoo| ©Robby Gragg

North of the city, in Lincoln Park, there is a zoo that opens its doors 365 days a year to all those who are interested in knowing what is behind the existence of many of the most important animals of the fauna of our planet. It is one of the largest spaces created for animal conservation in the country and, therefore, it is not surprising to know that inside you will find everything from black rhinoceroses to bears, gorillas and chimpanzees.

However, the real attraction of visiting this zoo during the winter season is the fact that all the animals you will see originally live at the North and South Poles and come out to enjoy the cold temperatures of the season, as they are similar to those they would have in their polar habitats.

So when you visit Lincoln Park Zoo during the winter you will have the opportunity to see live and direct polar bears, seals and penguins enjoying a snowfall. Without a doubt, this is one of the best things to see or do in Chicago with kids.

9. Skate on the curious ice rink at Millennium Park

McCormick Tribune| ©chrismetcalfTV
McCormick Tribune| ©chrismetcalfTV

Traditionally, Millennium Park is a must-see area of the city if you visit Chicago at any time of the year. However, winter is an even more special time to visit this place full of modernist sculptures and so close to the tallest skyscrapers in the city. From early November to mid-March, an ice skating rink is open, which stands out for its curious circular shape, like that of a ring.

It is preferable to go after sunset because there is a greater chance of encountering one of those beautiful snowfalls that characterize winter in Chicago and also to enjoy panoramic views of the illuminated skyscrapers.

In fact, this is one of the best things to do in Chicago at night during the winter season, because it combines a physical activity that will keep you warm, while you can be outdoors without having to settle for an enclosed, artificially heated facility. Keep in mind that in order to access the rink you must make an online reservation indicating the day, time and number of people who intend to simultaneously access this fun ice skating experience.

10. Tour Snowy Lincoln Park

Snowy Lincoln Park| ©Dottie B
Snowy Lincoln Park| ©Dottie B

Lincoln Park is another Chicago hotspot and a favorite place to go to enjoy the snow in some of the parks that are close to the periphery of Downtown.

As you can imagine, going to this park to play in the snow or to enjoy the views of Lake Michigan is also one of those excellent plans to see and do in Chicago during Christmas because of the economic savings.

It is an urbanized walking trail ideal for sports while being located very close to several neighborhoods with a vibrant cultural and gastronomic offer that can occupy the rest of your day without any inconvenience.

Temperatures in Chicago during the winter

Christmas Eve in Chicago| ©Tracy Reddington
Christmas Eve in Chicago| ©Tracy Reddington

Chicago is a fairly cold city and, as such, you can expect temperatures to be around 0° Celsius for most of your winter trip. For example, the usual high for the month of February is 4 or 5 degrees Celsius, while by the end of March everything starts to become more moderate with temperatures that are a little closer to 10 degrees Celsius.

Still, that shouldn't limit you from enjoying all the things to see and do in Chicago.

Book a Chicago street art tour

Chicago's winter tourist crowds

Millennium Park Tree Lighting| ©Emma Krupp
Millennium Park Tree Lighting| ©Emma Krupp

With the exception of Christmas and St Patricks Day weekend, it is unusual for tourism in Chicago to be unsustainable and overwhelming. However, you can't overlook the fact that it is the third largest city in the entire United States and the tourist influx is always significant throughout the year.

Book a minibus tour of Chicago

What to pack to visit Chicago in winter?

Preparing your luggage| ©Marissa Grootes
Preparing your luggage| ©Marissa Grootes

Clearly, it is essential that you pack plenty of winter clothing in your luggage if you intend to visit Chicago comfortably during the winter months.

Don't overlook this recommendation, as this is a city where snowfall usually lasts for several days and snow will be a reality for most of your trip.

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