Best Times to Visit Chicago – What To Prepare

5. Best Times to Visit Chicago1
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Do you want to know when to go to Chicago? Since I have spent the majority of my life in Chicago, I have created a month-by-month guide to assist you in determining the ideal time to visit Chicago based on your interests and preferred weather.

What Is The Best Times To Visit Chicago

Depending on what you hope to get out of your trip, there is a best time to visit Chicago.

If you want short lines and cheaper hotel and flight rates, and don’t mind cold weather, coming in January, February, or November might be the best choice for you.

If you want to visit Chicago in the summer to take part in food and music festivals, boat cruises, outdoor dining and rooftop bars, and beaches, June-August are the most popular months for tourists and locals looking to enjoy the best entertainment that the city has to offer.

If you want something in-between, coming in March-May or September-October means fewer crowds, average prices, and still plenty to see and do!

In this article, we break down the month-by-month guide so you can experience the best of Chicago no matter what month you choose to travel there.

Visiting Chicago In The Spring

Generally speaking, spring is a great time to visit Chicago because the weather starts to warm up, making it more pleasant to stroll around and take in the sights. However, the weather in the early spring can be very erratic. The season may continue into early spring, or the temperatures may be more tolerable and pleasant.

Pros: Warmer weather makes it easier to explore and go for walks.

Cons: You might still experience winter weather in the spring because the weather is so erratic, especially in March and early April. For spring break and St. Patrick’s Day, tourism increases in mid-March. celebrating St. Patrick’s Day. Bring a travel umbrella because it might rain even though it’s warmer outside.

Visiting Chicago In The Summer

Although some days can be uncomfortable hot and muggy, summer is the busiest and most popular season to travel to Chicago. Throughout the summer, there are a ton of free outdoor festivals, concerts, and events taking place all over the city. Free fireworks are only displayed twice a week at Navy Pier during the summer. On Chicago’s numerous patios and rooftops, you can also take pleasure in dining and drinking al fresco.

Pros: Summer is a busy season for festivals, concerts, and other events. It’s warm enough outside to visit the beach and enjoy the outdoors.

Cons: On some days, it might be too hot and muggy; there are more visitors in town, so the attractions are busier; hotel rates are higher; and crime is more prevalent.

Visiting Chicago In The Fall

Fall is typically the best time to visit in terms of good weather because the temperatures are usually better (still warm and less likely to rain). Fall temperatures vary and can be less predictable. Many of the same Chicago outdoor activities that you can enjoy in the summer (architecture river cruises, outdoor festivals, outdoor dining), but without the crowds, are still available in the early fall (September and early October). Temperatures in late autumn (late October and November) can feel like summer, fall, or even winter.

Pros: Typically, the most pleasant season is fall. Due to students going back to school, attractions are less crowded.

Cons: The fall season’s temperatures can vary greatly from year to year. Fall days that are colder than usual and feel more like winter may occur.

Visiting Chicago In The Winter

Although it’s not always the case, Chicago can get very cold—think of below-freezing temperatures and snow. Winters can occasionally be mild, and even during a colder winter, sporadic mild or warm days can occur. If you can, visit Chicago at a different time if you’re someone who doesn’t like the cold. There are plenty of indoor activities in Chicago, including museums, fantastic restaurants, tall buildings, shopping, theater, comedy clubs, and more, if winter is your only option. If you can arrange a last-minute trip, look at the weather predictions and decide to go if it won’t be too bad.

Nevertheless, if you don’t mind the cold, Chicago is a great place to visit in the winter because there are fewer tourists there, which means that everything will be less busy (aside from the busy holiday season between Thanksgiving weekend and New Year’s when people come to Chicago for holiday events and shopping). Keep an eye on the weather forecast for major snowstorms, which occur once or twice each winter even if you don’t mind the cold and snow. On your way in or out of town, you might experience flight cancellations and find it challenging to get around because of them.

Pros: In December and the first few days of January, Chicago offers a wide variety of holiday activities. Low season (January and February) means fewer people visiting attractions and generally less expensive lodging.

Cons: It can be difficult to enjoy outdoor activities when it is cold and snowy outside (although you might be lucky and have nice weather), the river or lake may be frozen, and there may not be any architecture cruises, lake cruises, or water taxis available.

When To Visit Chicago For Families And Kids

From June to September is when families most frequently travel to Chicago. This summer offers a variety of activities that are suitable for families.

However, if you are traveling with children, I advise booking your trip for August because attractions can be very pricey and crowded in the summer. This is the least expensive month of the summer season, and it will be less hot and muggy than July.

If you can coordinate your schedule with your children’s school schedules, April would also be a good time. There will still be a variety of family-friendly events to choose from, and the weather won’t be as hot. Additionally, there is always free admission to the Lincoln Park Zoo!

When To Visit Chicago For Food

Chicago is a fantastic location for foodies, just like any major city. Attend the Chicago Pizza Party in February to sample deep dish pizzas, or the Chicago Hot Dog Fest in August.

During Chicago Restaurant Week, a two-week event where you can enjoy fixed prices for multi-course meals from some of the city’s best restaurants, your visit may fall between mid-March and early April.

During the summer, Chicago hosts its two largest food festivals. In July, there is Taste of Chicago, a five-day event held in the Chicago Loop. In addition, the September Millennium Park hosts the Chicago Gourmet Festival, a high-end fine dining event.

When To Visit Chicago To Avoid Crowds

Winter is the best time to visit Chicago if you really want to stay away from the crowds and have a more relaxing vacation. In January and February, hotel occupancy rates are at their lowest level ever.

Despite the fact that Chicago winters are notoriously cold, now is a fantastic time to visit if you want to enjoy all of the indoor attractions this wonderful city has to offer without paying exorbitant prices. The restaurants and museums will be much less crowded than they are during other seasons, and theater tickets should be easy to come by.

In addition, visiting the sites during the week as opposed to the weekend is the best option if you want to deal with fewer crowds, regardless of the time of year.

5. Best Times to Visit Chicago2

When To Visit Chicago For Arts And Culture

In terms of arts and culture, Chicago is undoubtedly a center. More than 100 performances take place during Theater Week, which lasts ten days in February. Chicago Dance Month, which takes place in April, features more than 50 performances in addition to other activities and inexpensive classes.

The summer months in Chicago are known for their numerous music festivals. The most well-known of these is probably Lollapalooza in July, but there are numerous other music festivals of all kinds in between, including Riot Fest in September, Do Division in June, and many others.

On particular days, many renowned museums in Chicago, including the Money Museum and the Chicago Children’s Museum, offer free admission.

Faqs About When To Visit Chicago

The Wettest Month In Chicago Is Which?

In Chicago, May typically has the heaviest rainfall. During this month, precipitation totals are on average 4.76 inches. It is believed that the months of April, May, June, July, and August comprise the rainy season.

What Is Chicago’s Coldest Month?

Chicago experiences its most extreme cold in January. The average high temperature for this month from 2010 to 2019 was 31 degrees Fahrenheit, and the average low temperature was 17 degrees Fahrenheit.

What Is The Hottest Month In Chicago Each Year?

In Chicago, July is usually the hottest month. July’s average high is 73.9 degrees Fahrenheit. Although July and August are frequently very close in temperature, August is occasionally the hottest month. The average temperature in August is 72.5 °F, closely following.

How Long Do You Need To Stay In Chicago?

Visit Chicago for three to seven days at the very least. In addition to the museums in South Loop, the bars and restaurants in West Loop, the stores on Michigan Avenue, and other amenities, The Loop is home to a number of well-known landmarks. Take a look at our 5-day Chicago itinerary.

Is A Trip To Chicago Worthwhile?

There is no doubt that visiting Chicago is worthwhile. Whatever your interests, there is a lot to do. For fans of the arts, there are world-class museums, live theater performances, and sports teams as well as numerous outdoor festivals and other events that take place all year long.


The best times to visit Chicago are from April through May and from September to October, when the weather is warm, a variety of festivals are held, and the crowds are manageable. Chicago experiences its busiest travel and festival season in the summer as visitors from across the nation attempt to take advantage of the pleasant temperatures and wide range of activities.

If you want to find more interesting and beautiful places to vise, welcome to check our best-time-visit guide below!

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