If you’re planning on visiting Chicago, you’ll be glad to hear that the city features plenty of things to do. Tourists are sure to never be bored thanks to world-class museums, live music events, award-winning food, and architectural marvels. Though you’ll find Chicago to be lively year-round, your experience in the city can vary greatly depending on the time of year you visit. Weather fluctuations and seasonal events play a big role in how you’ll enjoy everything Chicago has to offer.

Here at American Auto Insurance, our team of locals wants to help you plan your next trip to the Windy City. Read on to learn what it’s like to visit Chicago across the different seasons and discover which season is best for tourists. We’ll discuss key factors, including what the weather is like and which events you can check out during your stay.

Visiting Chicago in the Winter

A view of downtown Chicago taken at the Bean aka Cloud Gate

Chicago by Pedro Szekely is licensed with CC BY-SA 2.0

As you might expect, Chicago has a continental climate that features cold winters. Be sure to bring your mittens, gloves, boots, and winter coats if you visit anywhere from December to February. December is a little warmer with an average low of 23 F and an average high of 36 F with these figures dropping to 18 F and 32 F in January. If you’re able to bear the cold, winter can be a magical time to visit.

December is particularly popular among tourists who want to embrace the holiday spirit. You can go ice skating at Millennium Park while viewing the city’s Christmas tree or check out a performance of “A Christmas Carol” at Goodman Theatre. Many tourists visit Christkindlmarket at Daley Plaza, which is a German-themed Christmas market. If you forget winter clothes and need to do some shopping, be sure to go to Macy’s and meet Santa while you’re at it. You can also ring in the new year at a hotel ballroom like The Drake Hotel or London House on Magnificent Mile.

Even if you visit after the holidays are over, you can still have a fun Chicago winter. Ice skating at Millennium Park is still open in January, and the annual Chicago Auto Show takes place in February. You can also take advantage of indoor museums, theaters, and restaurants.

Visiting Chicago in the Spring

Those who prefer a little bit of warmer weather might want to put off their trips to Chicago until the late spring. The lowest temperatures are March’s average low of 29 F and average high of 43, and it’s only uphill from there. Especially if you visit earlier in the spring, err on the side of caution by packing for the possibility of rain and unusually cold temperatures. Tourists who come in March will get a kick out of the city’s St. Patrick’s Day celebrations. You can see the green-dyed Chicago River and participate in pub crawls and parades.

The Major League Baseball season starts in late March, so consider watching a White Sox or Cubs game. Another spring activity includes the Garfield Park Conservatory Spring Flower Show, which is perfect for celebrating the end of winter. You’ll also appreciate Maifest Chicago in May if you want to experience a German festival with plenty of food and live music.

Visiting Chicago in the Summer

Summer is one of the busiest times to visit Chicago. In addition to crowds, expect temperatures to fluctuate between the low 60s to the low 80s. High humidity and strong breezes from Lake Michigan can throw things off, so be sure to pack clothes for warmer and cooler weather. June is a great month for festival enthusiasts, as you can experience everything from the Chicago Blues Festival to the Taste of Chicago food festival.

Celebrate the Fourth of July by watching fireworks at Navy Pier or Oak Street Beach. Other July highlights include the Pitchfork Music Festival and the Square Roots festival. Outdoor events persist into August, with the annual Chicago Air and Water show taking place along North Avenue Beach and the Lakefront. Barbecue lovers should be sure to check out the annual Ribfest in Northcenter.

Visiting Chicago in the Fall

The temperatures start to cool down during the Chicago fall. September begins with an average high of 73 F, which drops to 47 F by November. The crowds aren’t as dense, as the end of the busy tourist season correlates with the end of summer. You can find live music at Millennium Park in the form of the Chicago Jazz Festival. Celebrate the start of the National Football League season by watching a Bears game at Soldier Field. If football isn’t your thing, wait until October to see a Bulls or Blackhawks game at the United Center.

October is also a good time to go on a haunted history tour of the city. Keep in mind that the Chicago Marathon causes hotels to fill up fast, so plan accordingly. Another highlight is the Chicago Thanksgiving Parade on Thanksgiving morning, so consider watching it live from State Street instead of from your TV.

What’s the Best Time To Visit Chicago?

While the best time to visit Chicago is subjective, we think the fall is a clear winner. It allows you to avoid the frigid winter temperatures and overwhelming summer crowds while still offering plenty to do. Here’s a closer look at some Chicago fall events to consider attending:

  • Oktoberfest. Chicago is a great place to celebrate Oktoberfest thanks to the city’s historically German population. This event provides everything from live entertainment to craft beer tastings.
  • Chicago Film Festival. Whether you’re a film buff or want to experience the city from a new perspective, consider going to the Chicago Film Festival. It’s North America’s longest-running competitive film festival and seeks to highlight diverse pieces of international cinema.
  • Magnificent Mile Lights Festival. The annual Magnificent Mile Lights Festival kicks off the holiday season through its all-day celebration. A parade takes place down North Michigan Avenue along with family-friendly activities.

We hope this guide helps you plan your next trip to Chicago accordingly. If you know of any other seasonal activities tourists should know about, be sure to let us know here at American Auto Insurance or give us a call at 773-286-3500. Our team appreciates your contributions to helping others enjoy our beautiful city.


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