10 Things to Do in Chicago in Winter

Chicago is one of the coldest cities in the US, so here are some plans that will guarantee you 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 you think of plans in Chicago, they abound at 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.

Below, I've listed all the activities I've compiled 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 American Hockey League season and the NBA regular season extend into the winter months. At the same time, Chicago's United Center is home to the Chicago Blackhawks and Chicago Bulls, two of the top teams in their respective sectors of the industry, so you can be sure that attending a game of either team can be an extremely fun experience. Plus, both sports are easy to follow, even for non-fans.

Plus, it's a fun way to escape 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 and enjoying a very American tradition.

Book your ticket to 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's day, one of the most important massacres in the history of the American Mafia took place. It was motivated by clashes between Al Capone's group and 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 took place 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 organisations had on the city.

Book a mafia and crime tour of Chicago

3. Celebrate New Years Eve like the locals do

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

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

However, there are certain traditions that locals follow to give the New Year's Eve celebration a much more authentic feel 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 Chicago Bay on Lake Michigan. So, I suggest you head to these areas if you're looking for a plan that's quite similar to what you'd experience in New York's Times Square.

Greet the New Year with a helicopter ride over Chicago

On the other hand, if you're really interested in participating in something unique and budget constraints are not an issue 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 in the new year in style, enjoying panoramic views of a city as big and modern as this one.

Book a helicopter tour of Chicago

4. Take a ride over 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 freeze over, offering its inhabitants a quite unique landscape that is worthy of being admired by any tourist who appreciates 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 get to know an important tourist area of Chicago. Concrete Beach, Navy Pier and the entire Museum Campus area. It is worth noting 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 well worth a visit.

On the other hand, Chinatown and Greektown are two immigrant neighbourhoods that are relatively close to this public park area. It's also a good idea to join one of the Chinatown food tours that focus on this type of food if you're feeling peckish after walking several kilometres of waterfront.

Book a ticket to the Field Museum of Natural History

5. If you're 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. If you're a spectator on the shore, you can also enjoy the Parade along the Magnificent Mile or go into some of the Irish pubs in the area.

Book a cruise on Lake Michigan

6. Be sure to catch a play or musical event.

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

The winter season is a busy time for Chicago's theatre and music scene, as it's a great way to escape the cold weather that characterises the early months of the year. The Chicago Theatre usually has at least 2 shows with season-long dates and the occasional special weekend concert.

The Chicago Symphony Orchestra'swinter concerts are another winter cultural event you shouldn't 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 renowned in the city.

7. Party on Presidents Day

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

Holidays are rare in the United States and when they do occur, they are arranged to coincide specifically on a Monday, just like 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 neighbourhoods where the nightlife is most interesting during this weekend that precedes the third Monday in February.

Also, if you are looking for a good plan to tour the city comfortably on this holiday, don't hesitate to book the Chicago sightseeing bus. It's an ideal day, as there's hardly any traffic as many families have gone to the outskirts of the city to take advantage of this little holiday.

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

Just north of the city, in Lincoln Park, is a zoo that is open 365 days a year to anyone interested in learning about what lies behind the existence of many of our planet's most important wildlife. It is one of the largest conservation zoos in the country and it is not surprising to learn that you will find everything from black rhinos 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'll see originally live at the North and South Poles and come out to enjoy the cold temperatures of the season, which are similar to those they would have in their polar habitats.

So when you visit Lincoln Park Zoo during the winter you'll have the chance to see 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 Millennium Park's curious ice rink

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 city's tallest skyscrapers. From early November to mid-March, an ice skating rink is open that is notable for its curious circular, ring-like shape.

It's best to visit after sunset because of the greater chance of encountering one of the beautiful snowfalls that characterise 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. Please note that in order to gain access to 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 favourite place to go to enjoy the snow in some of the parks that are close to the edge of Downtown.

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

It's an urbanised hiking trail that's ideal for sports while being close to several neighbourhoods with vibrant cultural and gastronomic offerings that can fill 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 February is around 4 or 5 degrees Celsius, while the end of March starts to become more moderate with temperatures approaching 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's 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 influx of tourists is always significant throughout the year.

Book a minibus tour of Chicago

What to pack when visiting Chicago in winter?

Packing your luggage| ©Marissa Grootes
Packing your luggage| ©Marissa Grootes

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

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

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