When to Visit Chicago

Planning your visit to Chicago? Consider seasonal changes in weather and pricing when planning to explore this world-class city.

Every season gives Chicago a different air and appeal. Summer is the city’s most popular, which means streets teeming with tourists, higher wait times at restaurants and peak prices for most hotels. On the flip side, the wonderful weather brings al-fresco dining; neighborhood and downtown festivals galore; flowers everywhere; twice-weekly fireworks at Navy Pier; splendid boat cruises along the Chicago River and Lake Michigan; beach-time fun, from sand volleyball to surfing to simply sunning; and the general vitality of a city that is sincerely grateful for the chance to toss coats, hats, gloves and other cumbersome clothing. If you’re visiting, be sure to ask hotels about any special summer packages, because tourist season also inspires special offers that can make the most of your budget.

The fall has its color-scape of changing leaves and the real feel of autumn, with breezy nights and lingering warm-weather days. Plus, Chicago hotels often begin off-peak rates after Labor Day, so the period before daylight savings time ends (usually the first weekend in November) can offer a perfect balance of pleasant weather and pleasing prices. Halloween is a big deal here, with a city-sponsored festival and pumpkin patches that pop up even around the city. It’s also the time that theaters, sports teams and dance companies often kick off their seasons. Just know that from September through November, there are often large conventions that fill up hotel rooms throughout the city.

From the moment Halloween wraps until after the New Year, Chicago is a whirlwind of holiday sparkle. From hot sales up and down the Mag Mile to tree lightings to visits with Santa, there are plenty of reasons to bundle up and get out. Note, though, that this marks a different peak season for the hotel industry and prices tend to climb once again. Until Christmas Eve, which is so slow that great deals can be found for those who want them. And though we can’t guarantee every Christmas is a white one, it’s without doubt the most festive time of the year. In terms of hotel prices, New Year’s Eve is yet a different story, with special packages making for sometimes pricey nights.

Spring takes a little while to appear—sometimes not until mid-May—and it never seems to last long enough, but it also presents fair temperatures and the pretty budding of flowers and trees. March and April can be a bit chilly still (it’s even been known to snow), but the city can get busy with convention groups during these months as well, so be aware as you make plans. As Memorial Day hits, the beaches and pools open, and city fests begin in earnest. It also marks the beginning of peak tourist time as far as pricing goes.

It’s a silly old joke, but it truly does apply to Chicago: If you don’t like the weather, wait five minutes. The city’s unpredictable climate stems partly from its location halfway between the equator and the North Pole and in the center of the continent. Winters are particularly annoying for their crazy ups and downs; you wake up shivering to negative windchills and by the afternoon, it’s pushing 40. One day it snows 6 inches, and the next day melts it all away (no complaining there). The best winter weather tip is to be prepared: Wear layers, and never underestimate the biting winds.

Which brings up the city’s notorious nickname: the Windy City. It often seems perfectly suited, but Chicago actually ranks only about 75th on a nationwide list of the windiest cities. Although the term may have been used first to describe the gusts off Lake Michigan, the name stuck as a reference to city boosters who tooted Chicago’s horn to win the 1893 World’s Columbian Exposition. But that doesn’t mean it isn’t windy. Plenty of breezy days blow umbrellas inside out, and canyonlike wind tunnels between downtown buildings keep moms holding tight to little hands and can force even grown men to walk at an angle.

Despite grumbles from locals that Chicago has merely two seasons—“winter and road construction” (the city is, indeed, amok with road construction from May to October)—Chicago is a four-season town, however loosely interpreted by Mother Nature that may be. Spring, in particular, seems to laugh heartily at the calendar, usually shuffling in around mid-May, bringing rain showers and thunderstorms. Even into June, you’ll still want to carry a light jacket, especially when attending an outdoor evening concert.

July tends to be Chicago’s hottest month, and August surprisingly the wettest. Both are often accompanied by unpleasant, Gulf of Mexico-born humidity, sending curly heads into a frizz and making straight-haired ones fight for their lives. That’s why the lakefront is so cherished. Meteorologists talk about “lake-effect” breezes that typically result in cooler temps by the lake during warm months and warmer breezes on colder days. Thank goodness for the fall, often cited as Chicago’s best season, when trees show off their rainbow of colors, humidity takes a dip, and temperatures still hover around 70. Come November, it’s back to snow country and airflow from Arctic Canada. Silk long underwear helps.

This information originally appeared in the "Insiders' Guide to Chicago" and is ©2012, Morris Book Publishing/Globe Pequot Press.