Best Time of Year to Visit Chicago



What is the best time to travel to Chicago? That depends on your tastes, but most people share the opinion that Chicago has one of the most pleasant late springs and summers on the books. Take a moment to learn about why these times are the best times to visit Chicago. Then, if you’re planning a trip, take a moment to learn about “The Ledge,” a 360-degree view of the Chicago metroplex, Lake Michigan, and four other states, from the top of Willis Tower.

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Why Are Late Spring and Summer the Best Times to Visit Chicago?

The best time to travel to Chicago is subjective. Some of you may be traveling from the south to get a refreshing taste of winter, while others among you may be eager to see the leaves turn during those famous Chicago autumns. No matter which time you visit the city, you’ll find plenty to do, and each of Chicago’s seasons are quite distinct and offer their own charms. That said, most people will agree that the best time of year to visit Chicago is between May and September. Why is this, you ask? Let’s take a look at a few key reasons: 

Temperate Weather: 

The weather in Chicago from between May and September is practically room temperature, and even when it’s hot, the temps remain quite gentle.

  • May – Average Temps (Low/High):  48.4/70 °F
  • June – Average Temps (Low/High):  58.1/79.7 °F
  • July – Average Temps (Low/High):  63.9/84 °F
  • August – Average Temps (Low/High):  63/81.9 °F
  • September – Average Temps (Low/High): 54.3/74.8 °F

Street Life

During the fall and winter, you’ll see some pedestrians on the streets. The city never quite shuts down, no matter the weather. That said, during late spring and summer, Chicago turns into a thriving, hip, vivacious city that can compete with the best. Every block comes alive with vendors, shoppers, and street artists. Best of all, you’ll stumble upon street fairs every other block. That’s right. 

There seems to be an endless stream of block parties in this time of year, where you’ll find local artisans selling their wares, local restaurants cooking up something special, and local bands rocking like there’s no tomorrow. Believe it: when the weather is good, Chicago is a party city.

Beach Life

One more reason this time frame is the best time of year to visit Chicago is that you’ll be able to swim in Lake Michigan. Many tourists are surprised to learn that Chicago has some of the best beaches in the country. In fact, our coastline is often referred to as “The Third-Coast.” That’s because Lake Michigan is about the size of Western Virginia, and anyone standing on the coast of the Lake will agree that it’s so vast, it’s just like a trip to the ocean—minus the salt! 

In total, there are 24 beaches along the Chicago lake front. Nearly all of the beaches are close to restaurants, bars, and include wonderful views of both the Chicago skyline and of Lake Michigan. In particular, we recommend Montrose Beach, North Avenue Beach, Oak Street Beach, Ohio Street Beach. 

Let Skydeck Chicago Make Your Trip One to Remember 

Remember that, the best time to travel to Chicago is a matter of tastes. There are plenty of reasons why some tourists may claim autumn and winter as the best time to visit Chicago. Regardless of when you choose to visit, be sure to head to the top of Willis Tower for a 360-degree view of Chicagoland with Skydeck Chicago. 

And on your way up to the top? You and your family will make your way through an interactive museum designed specifically to give you ideas of all the fun things to do and places to visit throughout the Windy City. This museum easily ranks among the best in the city! If you have any questions, don’t hesitate to reach out