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Most Chicago visitors find the ideal times to visit are late spring and early fall. In the spring, you soak up blossoms, blooms, and equable temperatures. Spring in Chicago may be short, but it's widely welcomed. Some Chicagoans, eager for warm weather, lie out on roof-deck lounge chairs in 55-degree April weather. Fall provides crisp, clear days with idyllic balmy interludes. Pleasant weather sometimes lingers into late November.
Chicago has a reputation for being extremely cold in the winter. Daunting days of –40 degree wind chills do sometimes occur. Salt trucks rumble over Chicago's frozen streets, and potholes large enough to swallow cars stop traffic. Summer isn't exactly a piece of cake, either. You may have strings of days when temperatures stay in the 90s and high humidity drains your energy.
But those are the extremes. Lake Michigan has a moderating effect on Chicago weather, air-conditioning the city in summer. (Of course, the lake also has a negative effect — the same breeze that cuts the humidity in the summer can bite straight through the thickest down jacket in the winter.)
Springtime in Chicago
Many of Chicago's 33 million annual visitors choose spring for their travels. But keep in mind that just because the days are warming up doesn't mean that the weather is necessarily nice. Strong winds can blow, and buckets of rain can fall during long strings of gray days. Spring is also the time of year (along with winter) when theater shows may close for a week. Performers need vacations, too.
Summer in the city
In Chicago, summer is festival time. Chicagoans jam-pack their summers full of outdoor activities — so much so that the choice of activities on weekends can be overwhelming.
Festivals can also be hot and cramped — then again, that's the point, right? — and because of the heat, everyone is at the lake, making the area a congested free-for-all: inline skaters skating into bikers who are biking into runners who are running into Fido, who just broke off his leash!
Remember that the air may be hot and humid, but you can usually count on a cool lake breeze. If you're venturing to the suburbs, however, the temperatures there can be 10 degrees higher.
A fall to remember
In Chicago, you get the best weather in the fall — still warm enough, but not so hot and humid. You have the best shot at an uninterrupted string of beautiful days. With openings for the opera and symphony seasons, the cultural scene is also back in swing. Then again, so is convention season. Your hotel room or restaurant table can be surrounded by dozens of computer geeks, dentists, or who knows?
Beware of unpredictable September or October heat waves. (Pack the shorts and sunscreen — just in case.)
Winter in the Midwest
Winter brings visions of softly falling snowflakes, but in reality those lovely snowflakes result in slick roads and salt trucks. While Chicago looks beautiful in winter, Michigan Avenue is packed, literally — so much so that making your way down the street can be a challenge.
After Christmas, a peaceful hush settles over the city. You can have Michigan Avenue to yourself on the weekdays and pretend that the city is all yours.
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