Chicago is a vibrant city known for its stunning skyline, rich history, and diverse culture. Each season offers a unique experience, making it important to choose the right time for your visit. The best time to visit Chicago will be when it’s the right time for you. Understanding the climate, events, and activities available throughout the year can help you plan a memorable trip.
While we spent our three days in Chicago in the spring, there’s nothing stopping you from going at a different time in the year. From the chilly winters to the lively summers, each month comes with its own charm and opportunities. We will explore the best times to visit Chicago month by month, highlighting what you can expect in terms of weather, festivals, and attractions.
I hope you learn about the various offerings throughout the city so you can decide when its the best time to visit Chicago.
This post contains affiliate links. This means if you purchase something from a link, I may make a small commission, at no cost to you. This helps me keep the site running and free.
If you like this post, be sure to sign up for my e-mail list for travel inspiration (and get your FREE budget printable), or connect with me on Facebook, Instagram, Twitter, or Pinterest.
Best Season to Visit Chicago Weather-Wise
Each season in Chicago offers a unique experience with its climate and special events. From the cold, snowy winter months to the vibrant, warm summer, timing your visit can enhance your satisfaction and comfort while exploring Millennium Park, Wicker Park, and Michigan Avenue. Spring and fall are often considered the shoulder seasons and can offer a sweet spot of enjoyable weather and moderate crowds. Though no matter what time, it’ll always be windy! Luckily, public transportation runs year round no matter the weather so you can get around!
Winter (December – March)
Chicago’s winter is known for its chilly cold weather, with January being the coldest month. If you don’t mind bundling up, you can enjoy the city with fewer tourists and often at a lower cost. The average temperature stays around 30-40°F, and the city turns into a winter wonderland with snow decorating the streets and parks. This could be a perfect time for cultural enthusiasts to visit indoor attractions and enjoy Chicago’s rich arts scene without the usual crowds. Don’t forget to check out the holiday season magic if you’re visiting in December!
Spring (April-May)
As the cold weather subsides, Chicago starts to bloom in the spring, especially from late April and May. This period is an ideal time to wander through Lincoln Park or enjoy a beverage in one of the city’s beer gardens. Festivals kick off, celebrating the warm weather, and public transportation makes it easy to reach every outdoor activity. The average temperature ranges from 50ºF to 70ºF, making for a comfortable exploration of the Windy City before the arrival of the summer crowds. For those looking for a balance between nice weather and manageable tourist numbers, late spring in Chicago might just be your perfect time to visit. Just be sure to pack in layers because once the sun goes down it can get very cold!
Summer (June-September)
Summer is without a doubt the high season in the Windy City. The warmer months from June through September buzz with energy, as North Avenue Beach, Millennium Park, and many outdoor venues host a multitude of events, including the famous Chicago Gourmet and the Chicago Jazz Festival. Expect average temperatures in the low 80s Fahrenheit, perfect for all sorts of outdoor activities. However, be prepared for the city to be filled with visitors, resulting in higher hotel rates and busier attractions. Despite the humidity, experiencing Chicago in full swing during the summer months can be exhilarating.
Fall (October-November)
Fall is a charming time in Chicago, with cooler weather setting in, displaying vibrant foliage throughout Lincoln Park and Grant Park. Temperatures can range from the 40s to 50s Fahrenheit – ideal for enjoying the outdoor beauty without the summer heat. October is often drier, but as November approaches, anticipate more rainfall. The fall season offers unique experiences like marathons and Thanksgiving celebrations, and it’s a quieter time for those wanting to escape the tourist rush. If you’re looking for a peaceful visit with the chance to see Chicago’s beautiful autumn colors, this is the time to come.
Month-by-Month Guide to Chicago
January
During January, Chicago is often at its coldest, with average temperatures lingering around the 20s to 30s degrees Fahrenheit. Frequently blanketed by snow, the city offers a winter wonderland atmosphere. January is also the coldest month, so visitors should dress warmly. Special events like the annual Chicago Restaurant Week towards the end of the month provide an opportunity to enjoy indoor activities.
Be sure to check road conditions before heading out and take advantage of Chicago’s efficient public transportation to avoid cold weather.
February
In February, Chicago’s weather remains chilly with averages similar to January, so layering up is essential. The city celebrates Valentine’s Day with romantic events and specials across restaurants. February can offer quieter attractions, given that it is off-peak tourist season. A key event is the Chicago Auto Show, the largest auto show in North America held at McCormick Place.
The off-season means you’ll be able to save money on accommodation in the city. Be sure to enjoy some of the museums of Chicago as well!
March
March in Chicago marks the beginning of spring, with weather starting to warm slightly, reaching average temperatures in the high 30s or 40s degrees Fahrenheit. It’s an exciting time with the city lavishly celebrating St. Patrick’s Day, including dyeing the Chicago River green. The month may still be windy, so visitors should come prepared with layers but especially gloves for your hands. The shoulder seasons offer more space and time to explore popular destinations like Millennium Park.
April
April sees further warming with average temperatures in the 50s degrees Fahrenheit, making it a more comfortable time for outdoor activity. The city blooms with spring and events such as baseball games and the Chicago Comic & Entertainment Expo add vibrancy. It’s a good time to visit spots like the Lincoln Park Zoo as the cold weather eases. Be sure to bring a mix of clothing options to accommodate fluctuating temperatures. We took a riverboat cruise as part of our Chicago CityPASS and while we were warm when the sun was up, as soon as the sun set, we were VERY cold!
May
As Chicago welcomes May, the average temperature rises to a more pleasant range of the 60s degrees Fahrenheit. Outdoor events begin to pick up, and public spaces like Grant Park and Maggie Daley Park become perfect places to visit. The Chicago Memorial Day Parade honors veterans with a grand parade through the city. For travelers, this marks the beginning of the ideal time to experience outdoor Chicago before the peak of tourist season.
June
June in Chicago brings warmer weather, with averages in the 70s degrees Fahrenheit, offering a sweet spot for visiting. The Grant Park Music Festival starts in June, offering free outdoor concerts. The city comes alive with activities along Lake Michigan, such as sunbathing at North Avenue Beach. Visitors in June should prepare for warm weather and long days. Don’t be afraid to hop on a bike and explore the city on two wheels! Our hotel, StayPineapple, provides bikes for their guests free of charge, but there are plenty of bikes for rent throughout Chicago.
July
July is one of the hottest months in Chicago, with average temperatures in the high 70s and 80s degrees Fahrenheit. It’s a prime time for the city’s outdoor festivities, including the Taste of Chicago in Grant Park and the Chicago Jazz Festival. The Fourth of July fireworks over Navy Pier are a must-see.
Be sure to stay hydrated and wear sunscreen when visiting Chicago in July! There are a lot of places to eat outside so you’ll be in the sun for longer than you think.
August
August maintains the warm weather with similar average temperatures to July. The month is packed with events, such as the Air and Water Show at the beachfront. Chicago also hosts the Chicago Gourmet food festival that showcases the city’s culinary delights. Travel advice for August includes planning ahead for events, as they can draw large crowds, and booking accommodations early to secure a spot.
Be sure to plan your itinerary in advance, especially if you want to attend any events. August is peak season in Chicago, so be sure to book accommodation early too!
September
As September arrives, average temperatures start to cool down slightly, making it an ideal time for those who enjoy warm, but not hot, weather. The city continues to buzz with events like the Chicago Jazz Festival and various neighborhood fests. September is the windiest month and still provides ample opportunity for outdoor activity. Be sure to pack a windproof jacket, especially if you’re taking a walking tour of Chicago!
October
The average temperature in October drops to a comfortable range in the 50s to 60s degrees Fahrenheit, offering beautiful fall scenery. Outdoor activities continue with events like the Chicago Marathon. October is an ideal time for exploring the urban outdoors, and travel tips include bringing a raincoat for the occasional showers. It’s the best time to visit Chicago to enjoy the fall foliage.
November
The temperatures in November further cool, heralding in the winter months with ranges between the 30s to 50s degrees Fahrenheit. The holiday season starts with the Magnificent Mile Lights Festival on Michigan Avenue. The city begins to dress up in lights and decorations, with fewer rain days than in October. Ahead of the holiday rush, November can be the perfect time to shop and enjoy the start of the festive atmosphere.
December
December sees Chicago fully in the embrace of cold weather, with average temperatures in the 20s to 30s degrees Fahrenheit. It’s the time for holiday markets, ice skating in Millennium Park, and New Year’s Eve celebrations. While it is among the coldest times to visit, indoor attractions such as the Chicago Cultural Center offer shelter and entertainment. Packing for the cold and taking advantage of Chicago’s festive spirit can make for an unforgettable end-of-year trip.
Final Thoughts
Visiting Chicago is always a splendid idea, and the best time to go depends on your preferences for weather, events, and ambiance. Whether you’re braving the cold to see the city sparkle during the holiday season or basking in the warm weather at one of the many summer festivals, there’s something for everyone. The shoulder seasons often provide the sweet spot for milder temperatures and fewer crowds.
No matter when you choose to visit the Windy City, you’re sure to find a bustling metropolis filled with outdoor activity, special events, and cultural experiences unique to Chicago.
Read More about Chicago
How to Spend Three Days in Chicago
Ultimate Guide to Public Transportation in Chicago
In Depth Review of Chicago CityPASS
Save “Best Time to Visit Chicago” for Later
