Visit Chicago in the summer or the fall.
We repeat, visit Chicago in the summer or the fall.
The Midwestern American winters are nothing to scoff at. They are downright frigid, and besides, there isn’t much going on during Chicago’s LONG and beaten winter months. We say LONG because while other places in the world are celebrating the beginning of spring, Chicago is participating in Winter Part 2, as the city is still owned by snow and freezing rain. So What is the weather like in Chicago Illinois year-round?
Well, let’s be fair to Chicago’s Winter Part 1 and Winter Part 2 because the summer weather isn’t that great either. It is suffocating in its humidity, and the hot, muggy weather, along with big crowds of folks partaking in festivals and other major attractions, can make for a miserable experience if you don’t have the right attitude.
So, we’ll be clear, Chicago didn’t become the second-most visited city in America because of its weather. This iconic city brings in 55 million visitors a year because of its impressive culture, cuisine, and sports, not the depressing weather.
The Basics of Chicago, Illinois, Weather and When to Visit
If you aren’t visiting Chicago for one of the many music or cultural festivals in the summer, the best time to visit is in the fall. The autumn months are normally sunny, but not hot, and the crowds are thinner as summer vacations have come to a close. The fall window is small, though, and includes late September to mid-November. The end of November does see snow sometimes, so if you are unwilling to slog through the snow with the locals then schedule a trip before then, just to be safe.
If you are open to fluctuating weather conditions that bring a mix of cold and warm weather, then April isn’t a bad time to go to Chicago. The lines are shorter at the major attractions and the hotel prices are lower, but you might be wrestling with snow plows and snow boots.
The most important thing when visiting Chicago is to plan ahead and make reservations early. The inexpensive and moderately-priced hotels sell out fast, especially on the weekends in the months of June, July, and August. You’ll also want to be on the lookout for conventioneers. Large conventions lock up hotels with thousands of people and send the price of available rooms soaring. Big conventions include the Restaurant Show in May and the Housewares Show in March. During those weeks, major hotels in downtown Chicago are booked solid, so you will be on the outskirts of town looking inward.
Take a look here for a searchable list of every convention in the City for the next 18 months to see if there is a clash. Total numbers of over 30,000 spell doom for your trip!
See the bottom of the article for some Chicago festivals that might catch your fancy or cause you to choose another time to go:
The Reason for “The Windy City” Nickname- It might not be what you expect.
As you head into Chicago, you surely are aware of the city’s nickname, “The Windy City.” In an article focused on Chicago weather – like this one – you should know the reason for this moniker. Assumptions are always made that it has something to do with the tireless winds that push across Lake Michigan to knock you over upon arrival. However, that theory is only partially true.
Besides being a very windy city, the nickname stuck because of its reputation of having boastful citizens and politicians, or “windbags” full of “hot air.” In fact, legend claims that New York Sun editor Charles Dana cautioned its readers to ignore the “nonsensical claims of the Windy City” in an 1890 article. See, New York and Chicago had a serious rivalry at the time, and the two cities were competing for the 1893 World Fair, which Chicago won.
The metaphorical jab by Dana stuck, it seems, but even historians are unclear which came first, the Lake Michigan breeze or the Chicago citizenry boasts. If it were only the wind that mattered, Boston would hold the crown, for it is the windiest city in America, with average wind speeds of 12.4 mph. Chicago comes in 12th, with an average of 10.3 mph. However, it is a little windier on the edge of the lake, so when you are flying into Chicago O’Hare, expect some turbulence.
Monthly Weather Conditions in Chicago, Illinois
People in Chicago wait for those perfect days between hot and humid summers and relentlessly cold winters. Those in-between days make this friendly town even friendlier because it is hard to beat this iconic city when the sun is out and the breeze blows back the humidity.
However, there is nothing predictable about Chicago weather in the spring and autumn months. Packing appropriately is essential. It might rain, it might snow, or you might get an 85-degree day. In many cases, you will wake up needing a winter coat, rain boots, and an umbrella, and downsize to a short-sleeve T-shirt by mid-afternoon.
The sunniest part of the year in Chicago is the four-month period from mid-June to the end of October. The clearest days of the year are at the end of August, but even then, it is clear, mostly clear, or partly cloudy only 68 percent of the time. The rest of the year, the sky is overcast nearly 60 percent of the time. Overall, Chicago has only 189 sunny days per year, while the U.S. average is 205.
May is the rainiest month of the year in Chicago, and the city sees 122 rainy days a year. October is the driest month. While there are numerous incidents of snow flurries in Chicago per year, the city averages 11 days a year in which at least one inch of snow accumulates. If you stay from the beginning of December to the beginning of March, you are likely to see some snow.
Here are the weather conditions you should expect to see from January to December, with average highs and lows, precipitation, and humidity as calculated at Midway International Airport:
What You Should Pack for a Trip to Chicago, Illinois
When packing clothes for Chicago, think “layers” because of the unpredictable weather. The following are tips for what to pack before heading to the Windy City:
- From fall to spring bring winter gear in the form of coats, hats, gloves, and scarves.
- In the winter, bring a set of thermal underwear, which helps block the chill. Thermals are a Chicago staple and your first line of defense against the cold. You won’t regret your decision to throw on a set before heading out of your hotel room.
- Your shoes should consist of casual, comfortable walking shoes and a set of rain or snow boots, depending on the time of year you plan to visit.
- There are some great spots for swimming in Lake Michigan, but the water temperature is usually pretty chilly even in the summer months. The best time to bring a swimsuit and flip-flops is August, with water temperatures topping out in the upper 70s, sometimes reaching 80 degrees.
- Regardless of the time of year, if you plan to travel to Chicago, bring a water-resistant jacket with a hood, and an umbrella.
- When visiting Chicago in the summer months, bring light breathable clothes because the humidity is a beast, along with a light jacket or sweater for the late evenings and early mornings.
No one visits Chicago for the weather unless they are a masochist. People visit Chicago because it is an iconic metropolitan city with a lot of history and culture – as far as American cities go. It also has a great festival scene that covers the things humans love the most from culinary and cars to music, art, and dance. Not to mention, the sports teams like the Bulls, Bears, and Cubs.
Chicago really has it all, and that is why so many people flock to the city, but the weather doesn’t always cooperate with the enthusiasm of its residents and tourists. If you find a few sunny days with low humidity, feel blessed, but be prepared for the worst and pack appropriately, and always do what the locals do, suck it up, and have fun anyways.
Chicago’s Festival Dates:
January or Early February
- Chicago Restaurant Week: For two weeks, you can sample food at discount prices at the very best Chicago restaurants.
- Chinese New Year Parade: Outside of China, you might not see a better celebration of the ancient Asian calendar, which dates back 4,000 years.
- Chicago Auto Show: The world’s biggest assembly of cars takes place in the Windy City, with around 1,000 automobiles on display, which is something akin to car porn.
- St. Patrick’s Day Parade: If you want to mingle with folks at 7 a.m. for a green beer, you will find them on the day of the annual St. Patrick’s Day Parade, which redefines “day drinking.” Here, the city dyes the Chicago River a blazing green, and bars are full of messy drunkards by noon. But this might be the best place in the world to experience Paddy’s day, even superior to Dublin!
- In June, the festival season kicks into gear, including the famous Chicago Blues Festival, which is a FREE, 3-day event that brings the biggest names in blues into town to get down with Chicago’s suburbanites. There is also the Ravinia Festival, a celebration of the symphony, chamber ensembles, and pop artists, the Chicago Gospel Festival, Chicago Pride, the Old Town Art Fair, and Wells Street Art Festival, which are held on the same weekend, and the Taste of Chicago, the largest FREE outdoor food festival in America that takes place over five days.
- Pitchfork Music Festival: Big headliners come around for this annual music festival at Union Park.
- Lollapalooza: This music festival used to tour America, but it is now an annual event that made Chicago its permanent residence. For nearly 30 years, this iconic event that ushered in a new age of summer festivals brings some of the biggest names in alternative rock and hip-hop.
- September is busy with the FREE Chicago Jazz Festival that cranks up on Labor Day Weekend, Riot Fest, a punk rock extravaganza with carnival rides and sideshows, and the much more civilized Chicago Gourmet that brings out celebrity chefs, and food and wine tasting.
- The tenth month of the year winds down the festival season with a film and dance. The Chicago Film Festival is a 2-week extravaganza premiering independent films from around the world and brings actors and directors into the fold for Q&A sessions. And Dance Chicago is one of the largest dance festivals in the world that runs for 6 WEEKS and brings around 50,000 dancers for competitions and workshops.
November and December
- If you can stand the beginnings of the winter season, you will be thrilled by the holiday atmosphere of the city of Chicago. The city really brings good holiday vibes with big city lights and bustling shoppers in big coats and hats. There are parades and tree lighting and the Magnificent Mile Lights Festival where thousands of lights kick off the season, along with carolers, Santa and his elves, and fireworks. It’s not quite Christmas in New York, but it’s a close second!
Have Your Say?
What time of year did you go to Chicago? What was the weather like? Did you brave the long Midwestern winters is head there during the summer months? Let us know if you have any comments or questions about our weather article below. We do love to hear from you!