The Ultimate Guide to Exploring Chicago in the Winter

Do not let multiple months of below freezing temperatures fool you, winter is actually the best time to visit Chicago. It is all in our ultimate guide!

Winter scene of Chicago

It is hard to imagine why anyone would visit “Chiberia,” as the city has been nicknamed. Locals will not argue with you (and certainly neither will Team Venta, we call Chicago home!), winter can be a tough time in the Windy City. But most Chicagoans will say the lake activities, beaches, music and street festivals during the summer make it worth braving the long winter. Despite its brutal months of harsh cold, snow, ice and wind, visitors still flock to Chicago throughout the winter.

There may be something more to the Windy City than just cold temperatures and freezing wind off the lake. Chicago was recently named the world’s best city for having it all, for the second year in a row! That should be reason enough to start planning your trip.

If you are thinking about visiting our friendly city this winter, or are a local needing some extra motivation to get out and about, look no further! We have put together the ultimate guide to enjoying and exploring winter in Chicago.

With all the fun activities we are about to suggest, you might actually forget about the negative wind chills!

Food Scene and Restaurant Week

Plate of food on table during Chicago Restaurant Week

For the foodies, Chicago is a mecca of some of the country’s, if not the world’s best restaurants. The food scene is incredible, no matter which neighborhood you choose to visit.

What is even convenient is that Chicago Restaurant week happens during the winter time. From January 26th until February 8th (2018), hundreds of Chicago restaurants partake in the event by offering pre-fixed menus. Prices range from $22 for brunch and lunch to $44 for dinner. There are over 370 participating restaurants this year! It is a great opportunity to get a taste of some of the best in the culinary industry.

Team Venta tip: Check out the hot new restaurants near our North American headquarters in the Fulton Market and West Loop neighborhood. There area is even nicknamed “Restaurant Row!”

Comedy Shows

Chris Rock performs comedy at Chicago Theater

Chicago has always been known for its strong comedy scene. With the star power that has come out of the famous Second City to the many open mic nights, Chicago is a great place to get your laugh on. Is there really a better way to spend a cold, snowy night, than laughing until it hurts at one of the city’s clubs?

Some of the city’s bigger performance venues like the Chicago Theater also host plenty of comedic talent. Plan your trip around your favorite comedian’s tour dates!

Check out these clubs for tickets and showtimes:

Zanie’s– featuring stand up

Second City – featuring sketch, improv

iO – featuring improv

Team Venta tip: Check out The Comedy Bar where you can enjoy a slice (or two) of delicious deep dish pizza at Gino’s East, then head upstairs for some of the funniest stand up comic routines.


Sue the T-Rex at the Field Museum in Chicago

Chicago is host to some of the world’s greatest museums. From housing the world’s largest, best preserved and most complete T-Rex skeleton ever found to an impressive collection of French Impressionist paintings, Chicago museums are not to miss. The nice part about Chicago’s museums is that a majority of the larger and more popular ones are located near one another, on what is called the Museum Campus. While not all of the city’s museums are located here, it does make it easier to travel from one to another.

This can easily be done with a special pass, called the City Pass Chicago or the Go Chicago Card.

Notable museums to visit:

Field Museum – for history buffs

Shedd Aquarium – for aquatic animal lovers

Museum of Science and Industry – for science and innovation enthusiasts

Chicago History Museum – for Chicagoans and visitors alike

Art Institute of Chicago – for art aficionados

Adler Planetarium – for star gazers

Some museums are free year-round while others offer plenty of free days or discounted days. To encourage visitors during the cold months, many of these dates fall during this time of year!

Team Venta tip: Visit the DuSable Museum of African American History: it is a fantastic collection of artifacts, photographs, stories and more promoting the appreciation of the achievements, contributions,. and experiences of African Americans.

Live Music

Live music in Chicago is popular among blues clubs

In addition to having a plethora of comedy clubs across the city, Chicago also boats a robust live music scene. Larger venues like The United Center and The Allstate Arena host big name acts with elaborate sets and shows. If you are looking for a smaller, more intimate show, there are plenty of venues throughout the city playing great shows almost nightly. From blues to rock to hip hop, there is something for everyone.

Check out some of these local favorites for a night of live music:

Kingston Mines

Tonic Room

The Hideout

Schuba’s Tavern 

Team Venta tip: Step back in time and check out The Green Mill, a jazz club straight out of the past! Prohibition era gangsters like Al Capone used to hang out there.

Art Galleries

Visit art galleries during the winter in Chicago

Have you noticed a theme yet? Chicago is an art lover’s city. Heading to an art gallery is a great way to support local artists, visit new neighborhoods and even meet new people. Chicago’s diverse population has created an eclectic art scene. Each neighborhood has its own feel and vibe, from high-end galleries to pop-up shows.

Check out these galleries to get your art fix:

The Renaissance Society 

Intuit: The Center for Intuitive and Outsider Art 

Stony Island Arts Bank

Richard Gray Gallery 

Team Venta tip: On your way over to say “hello” to us at our office, visit Mars Gallery for some colorful and exciting works of art in a unique space.

Professional Sports Games

Chicago professional basketball team Bulls
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We may be biased, but there is nothing quite like experiencing a Chicago professional sporting event in person. Our basketball and hockey teams have a long history of winning championships, which makes attending games an exciting experience.  Although the Chicago Bulls may not have won a national championship in recent years, the city’s other winter sports team, the Chicago Blackhawks have won 3 Stanley Cups trophies in the past 8 years. Whether you are a hockey fan or basketball fan, you do not have to worry about navigating to different arenas, as both teams share the United Center as their home stadium.

No matter which team you choose to support, you will surely have an exciting time. Games are high energy and offer a great alternative to staying in on a cold night.

Team Venta tip: Arrive early to check out the team memorabilia and the famous Michael Jordan Statue!

Visit the Venta Offices

Venta USA headquarters are in Chicago

We always like to let our Venta Community know we are available to take your orders and answer your questions in person. Stop in during our office hours and stock up on Venta products or chat with a sales rep. We are always happy to see you!

Our ultimate guide is always improving! There is so much to see in the incredible city of Chicago. We would love to hear what suggestions you have for great winter-time activities. Send us an email with your ideas! Email