The best times to go to Chicago

Famous for its icy winters, steamy summers and packed calendar of festivals, Chicago has something going on in every season. Yet while visitors will find something new every month or even week of the year here, some things remain constant: the city’s lively nightlife, cultured museums and animated neighborhoods are in full force all year long.

Events such as Lollapalooza and the Chicago Blues Festival have put the city on the national – and international – festival map. Other major events fill every month of the year, from championship sports to special museum openings, cultural fairs and community festivals.

Chicago shines in the summertime, when locals get relief from hot, humid days at lakeshore beaches and leafy, breezy parks. The calmer spring and fall have their own charms, while frigid winter sees lower tourist numbers – and plenty of snow and ice along the lakefront, as well as holiday magic.

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If you’re looking for a city break with phenomenal art and architecture, truly globe-spanning cuisine and exuberant festivals, the Windy City will keep you busy at any time of year. These are the best times to visit Chicago.

November to April is best for holiday celebrations and hotel deals

Weather in Chicago in winter: It’s cold. In winter, daily high temperatures in Chicago average around freezing – and can get much colder. Snow is the norm, with an average of about 40 inches falling per season.

Chicago winters are famously frigid and blustery, with a bitter wind blowing in from Lake Michigan usually taking many degrees off the just-above-freezing highs. Trees and bushes along the lakeshore become encrusted in ice, while plumes of steam rise over the skyscrapers.

But while the subzero temperatures scare many tourists away, bargains abound, particularly for accommodation. Travelers will have their pick of deals at hotels across the city throughout the winter months, while tables at top restaurants are easier to find.

In late November and December, the holiday season brings festive light shows to locations such as Lincoln Park Zoo; holiday markets and outdoor ice-skating rinks (especially the one at Millennium Park) are other seasonal delights. The icy tableaux along the lakeshore add some extra Chicago magic.

Michigan Ave bustles with holiday shoppers, and downtown shines with a million twinkling lights. Winter is the perfect time to warm up with some Chicago deep-dish pizza and make your own choice in the longstanding New York–Chicago pizza wars.

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January is Chicago’s coldest month, with temperatures dipping as low as 18ºF, and an icy wind blowing along the wind tunnels created by downtown’s skyscrapers. This is also the city’s snowiest month, with approximately 10 inches falling in an average year. Plan to stay inside as much as possible by taking advantage of the city’s restaurants and bars.

The city is still deep in the throes of winter in February, but there are plenty of events to keep you busy, such as the Chinese New Year Parade, Cupid’s Undie Run and Chicago Theater Week. Head up to the observation deck atop the former John Hancock Center for epic views over the frozen lake.

By March, many Chicago residents are wondering if the sun will ever shine again. Windy City–zens count the days during the grayest and windiest month, when temperatures rarely top 37ºF. Still, some fun events take the edge off the cold, including the city’s renowned St Patrick’s Day parade, when the Chicago River gets a shamrock-green makeover thanks to biodegradable dye.

As spring finally begins in April, the weather can be unpredictable. Be ready for sun, snow or rain – or maybe all three in the same day. That doesn’t put off sports fans, who flock to Wrigley Field and Rate Field for the opening of the baseball season.

The shoulder months (May and September to October) are best for culture without the crowds

Weather in Chicago in May, September and October: Daily temperatures range from about 50ºF to 70ºF – just lovely. Rain can often be in the forecast, however.

Chicago has two shoulder seasons – in late spring and early fall – when the city is either shaking off the winter chill or getting ready for it. Both are excellent times to visit, particularly if you plan to explore the city’s many marvelous museums.

Lovely temperatures bring a buoyant mood to the city. Budget travelers can find good deals on airfares and hotel rooms – though big sporting events and festivals can cause prices to spike.

In May, the weather finally warms up, spring rolls in, and everyone dashes to Chicago’s parks, lakefront trails, baseball stadiums and beer gardens. Beaches open on the Memorial Day weekend at the end of the month. The warming weather means a big turnout in the streets for community-focused festivals such as Sueños Chicago.

Kids go back to school in September, and beaches close after the Labor Day weekend, as Chicago’s peak visitor season begins to wind down. There’s still plenty on the cultural calendar, though, including Chicago Jazz Festival and Riot Fest.

Temperatures begin their drop in October. And while the baseball season is over, basketball and hockey fill the gap at the end of the month. Chicago Bears games and tailgate parties are in full swing, while more active types put their energies toward the Chicago Marathon.

Visit from June to August for festivals, beaches and baseball

Weather in Chicago in summer: Daily high temperatures usually sit in the mid-80s°F, sometimes reaching north of 90°F. Evenings are mild and lovely, with temperatures rarely below 60°F. Rain falls on a third of summer days, however – and thunderstorms during humid spells can be intense.

Warm weather and a packed festival calendar make summer the peak time to visit Chicago. Once school’s out, families descend on Chicago’s beaches in droves for fun in the sun, and museums are often crowded with locals and visitors. Expect to pay top rates for hotels and vacation rentals. You’ll also need to book sought-after restaurant tables and theater tickets well in advance.

In June, schools let out, and festival season ramps up. Hot days and frequent rain don’t deter the people from enjoying the first days of summer. Music festivals abound, including Chicago SummerDance, the Chicago Gospel Music Festival and the Chicago Blues Festival. Make time for the Chicago Pride Parade in Boystown, one of Chicago's most LGBTQ-friendly neighborhoods.

One of the most popular ways to see the city in summer is on a boat tour – and one of the best is run by the Chicago Architecture Center. The city’s glorious parks await: from art-filled Millennium Park, a ribbon of green runs south from downtown, following the shore of glittering Lake Michigan.

July is the month Chicagoans wait for all year. Festivals rock Chicago’s neighborhoods every weekend, with top billing going to Lollapalooza. Millennium Park hosts concerts nightly, and Taste of Chicago attracts visitors from all around the world, as fireflies glow everywhere. Things can get hot and humid – but with so much to enjoy, who cares?

August is a time for warm, sometimes sizzling weather, concerts, festivals, baseball games and beach frolicking. Tourists are still in Chicago en masse, so lodging prices are high, and lines can be long. Enthusiastic Cubs fans fill the stands at Wrigley Field (or stake out seats on the Wrigley Rooftops overlooking the stadium if they can’t get seats inside). Along the lakefront, check out the Chicago Air and Water Show, which features incredible displays from military jets screeching by overhead.