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When Is the Best Time To Visit Chicago?

January 25, 2023 By CityPASS

If you're getting ready for your next vacation, you're probably thinking about several different factors: the weather, the attractions, and cool things to experience while you're there. Considering these factors can make or break your trip — especially if you're counting on special events or seasonal attractions. So when is the best time to visit Chicago?

The Windy City changes with the seasons when it comes to both weather and things to see and do. You're sure to be in for an unforgettable trip whenever you choose to visit, but there are some things to know before you book your getaway.

Key Considerations for Choosing When To Visit Chicago

People often ask when the best time to visit Chicago is since this city has quite a reputation for its unpredictable weather. Through cold weather and hot temperatures, Chicagoans have seen it all. Even so, this city offers limitless possibilities, no matter the season.

When you think about when to visit Chicago, you have to consider other key factors, including fluctuating hotel rates and the influx of other tourists at peak seasons. Do you want to travel to Chicago during the music festival season? Or would you rather go when crowds are calmer, and more locals are on the streets? These things could really affect the kind of getaway you have in the Windy City.

Average Temperatures and Chicago Weather

There's a joke among Chicagoans that the city has four distinct seasons, often all in the same day. Chicago's weather fluctuates frequently due to the “lake effect,” or the breezes that blow off of Lake Michigan. These breezes can cool down a hot night or bring warmer air during the cold season.

Springtime in Chicago can be unpredictable depending on the month, as temperatures can range anywhere from 31℉ in early spring to 71℉ later in the season, on average. Even so, this is a beautiful time to visit when all of the city's green spaces are in full bloom. Things heat up in summer when temps range from 71℉ to 91℉, often accompanied by humidity.

If you don't like the heat, fall weather might be your sweet spot. In early fall, you can enjoy sunny days in the high 70s, with the weather growing colder in November, when the temperature drops to about 43℉. After November, make sure you've packed your winter gear since it gets downright cold in Chicago, with an average daily high of 38℉. However, it's not unusual to experience freezing temps and plenty of snow.

Costs and Expected Visitors

The best time to travel to Chicago if you're looking to save a little cash is in the wintertime. As the temperatures drop, so do the flight and hotel prices. Many travelers opt to explore Chicago in the summer to enjoy the warm, sunny days, but traveling in January, the coldest month, is when you'll find the best deals and the lowest crowds.

Summer is the peak tourist season in Chicago since there are festivals and outdoor events just about every weekend from Memorial Day through Labor Day. While you'll enjoy the beautiful summer weather, you'll also have to face throngs of other tourists and higher hotel rates and airfare.

Attractions and Cultural Experiences

Chicago has tons to offer throughout the year, but some attractions only come around during certain seasons. Summer is packed with food and music festivals, while November and December are dedicated to Christmas and the holidays. Think about if there are specific things you want to see or do when you visit Chicago, like Lollapalooza in summer or the festive Christkindlmarket that runs through the holiday season.

Ideal Times To Travel to Chicago

To help you decide when is the best time to visit Chicago, here are some things that make each season in the Windy City special.

Outdoor Festivals (Summer)

Summer is loaded with many outdoor activities for tourists and locals to enjoy. Some popular festivals that are uniquely Chicago are the Chicago Blues Festival in June, the Taste of Chicago throughout June and July, and the Chicago Jazz Festival in late August or early September. These festivals are hot spots to hear the best sounds, try the tastiest foods, and discover the heart and soul of the city.

Holiday Season and Indoor Attractions (Winter-Early Spring)

If you're headed to Chicago in the colder months, there's still plenty to do. For example, this city is known for its top-notch museums, including the Art Institute of Chicago, the Field Museum, and the Museum of Science and Industry. The last one on this list is especially exciting during the holiday season when it hosts the famous “Christmas Around the World” exhibit featuring decorated Christmas trees representing various cultures and nations.

To get more of the Christmas spirit, be sure to check out Macy's on State Street, where you can see the themed Christmas windows, all kinds of decorations, and the Walnut Room decked out with holiday cheer. Another of the best holiday events is ZooLights at the Lincoln Park Zoo, an activity that's perfect for the whole family to enjoy.

Least Crowded (Fall and Spring)

The biggest benefit of visiting Chicago in the spring or fall is seeing the most famous landmarks with smaller crowds. Soar to great heights at Skydeck Chicago or 360 CHICAGO with shorter lines, and enjoy smaller crowds in the museums, aquarium, and zoo. Even though these are low periods for seasonal activities and festivals, you'll have more time to explore when you cut out the big crowds and long queues for the city's best and most famous attractions.

The Bottom Line: There's Never a Bad Time To Visit the Windy City

As you can see, visiting Chicago in any season of the year is a great idea. Different times of the year bring exciting events, fun festivals, and cultural activities that highlight the best of the city. To sweeten the deal, you can save on Chicago's top attractions by purchasing a Chicago CityPASS® ticket that gets you into five attractions, or the Chicago C3® ticket that gets you into three.

Chicago CityPASS® tickets save you up to off compared to buying individual entrances, and the Chicago C3® ticket saves you up to . A CityPASS® bundle is your ticket to the Windy City's top attractions — and to significant savings!

Nearby Lodging

To get the most out of your stay in Chicago, we recommend finding lodging near Chicago's top attractions. Use this map to find the right lodging for you:

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