Famous for its blustery winters, steamy summers and skyscraping skyline, Chicago sees the full range of seasons. But thanks to a calendar packed with festivals and events, a rich foodie scene and a full hand of world-class museums to duck into when the evenings get cold, there's always something happening in the Windy City, no matter what month you visit.

With hot, humid days but plenty of lakeshore to catch the breeze, Chicago shines in the summertime, and spring and fall have their own charm. But with low tourist numbers and plenty of white stuff to bring the holiday magic, winter is an incredible season to see the city by the lake.

If you're looking for a city break with phenomenal art and architecture, truly globe-trotting cuisine and an exuberant festival season, Chicago has plenty to lure travelers at any time of year. Here's our guide to the top times to visit the Windy City.

Pulling up a slice of Chicago-style deep dish cheese pizza with tomato sauce.
There's never a bad time of year to eat Chicago deep-dish pizza © supitchamcsdam / Getty Images

Score big deals during Chicago’s low season (November–March)

Although Chicago's winter temperatures hover around the freezing point, that bitter lake wind can knock several dozen degrees off the highs due to the wind chill effect. But while below-zero temperatures scare many tourists away, bargains abound, particularly for accommodation. 

In late November and December, the holiday season brings festive light shows, holiday markets and outdoor ice skating rinks, and the frosty lakeshore adds some extra Chicago magic. Winter is the perfect time to warm up with some Chicago deep-dish pizza and form your own opinion on the city's feud with the New York-style pizza pie.

Travelers will have their pick of the deals on accommodation throughout the icy winter months, and tables at top restaurants are easy to find. Museums are less crowded, too, making the winter season the best time to explore the Art Institute of Chicago, one of the world's oldest, largest and most-visited art museums.

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The shoulder seasons (May & September–October) are great time to enjoy less crowded museums

Chicago has two shoulder seasons – in late spring and early fall – when the city is either shaking off the winter chill or preparing to head into it. Both are excellent times to visit. Temperatures are a manageable 50ºF to 70ºF degrees, and there's a bouyant mood in the city, although rain is often on the weather forecast.

With school in session and variable weather, the crowds are small, making this is the perfect time to check out Chicago's excellent museums and explore its world-famous architecture. Budget travelers can find good deals on airfares and accommodations, but keep an eye on the calendar; big sporting events and festivals can cause prices to spike temporarily.

Crowds pose around the famous Cloudgate sculpture in Millennium Park
The shoulder seasons in spring and fall see fewer crowds at top Chicago sights © Boogich / Getty Images

Enjoy fantastic festivals and baseball in the high season (June–August)

Warm weather and a packed festival calendar make summer the peak time to visit Chicago. School's out around this time, so 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.

One of the most popular ways to see the city in summer is on a boat tour, the best of which is run by the Chicago Architecture Center. Make the most of the city's many parks; art-filled Millennium Park marks the start of a chain of parklands running south along the banks of Lake Michigan.

Top summer festivals such as Lollapalooza and Taste of Chicago attract visitors from all around the world, and summer is also the height of the baseball season. Rabid Cubs fans take to the stands at Wrigley Field (or stake out seats on the Wrigley Rooftops overlooking the stadium if they can't get seats inside).

Enjoy cozy restaurants in January

January is Chicago's coldest month, with temperatures hovering around 22ºF, 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 and enjoy all there is to eat and drink here.
Key events: Buddy Guy's Residency (at Buddy Guy's Legends)

Top 7 winter day trips from Chicago 

Celebrate Chinese New Year in February

Chicago is still deep in the throes of winter in February, but there are plenty of events to keep you hopping around the city. Head up to the observation deck atop the former John Hancock Center for epic views over the frozen lake.
Key events: Chinese New Year Parade, Cupid's Undie Run, Chicago Theatre Week

The Chicago River dyed green for St Patrick's Day
The Chicago River goes green for St Patrick's Day © berni0004 / Shutterstock

March is all about St Patrick’s Day 

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 linger around 37ºF. However, some fun events take the edge off the cold, including the city's famous St Patrick's Day parade, when the Chicago River gets a shamrock-green makeover with biodegradable dye.   
Key events: Chicago Restaurant Week, Chiditarod, St Patrick's Day Parade

Baseball season kicks off in April 

As spring begins, the weather in Chicago 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 Guaranteed Rate Field for the opening of the baseball season.
Key events: EXPO Chicago, Cubs Home Opening Day, White Sox Opening Day

Embrace winter in Chicago by exploring these vibrant neighborhoods

Expect crowds in May

Finally, the weather warms, spring rolls in, and everyone dashes to Chicago's parks, lakefront trails, baseball stadiums and beer gardens. Beaches open at the end of the month over the Memorial Day weekend and hotels see a rising number of travelers checking in.
Key events: Mole de Mayo, Sueños Chicago

Chicago skyline, as seen from North Avenue Beach
Summer is the time to enjoy Chicago's long, lakeside beaches © f11photo / Shutterstock

Join the Pride Parade in June 

In June, schools let out, beaches get busy and festival season ramps up. The temperature creeps towards 80ºF, but it rains on a third of the days. That doesn't deter the people partying during Chicago's spirited pride celebrations
Key events: Chicago Blues Festival, Pride Parade

Lollapalozza takes over in July

July is the month Chicagoans wait for all year. Festivals rock Chicago's neighborhoods every weekend, with top billing going to Lollapalooza. Millennium Park has concerts downtown nightly and fireflies glow everywhere. It can be hot and humid, but with so much to enjoy, who cares?
Key events: Lollapalooza, Taste of Chicago, Pitchfork Music Festival

August is peak season  

Ah, more awesome summer weather. 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.
Key events: Northalsted Market Days, Windy City Smokeout, Chicago Air & Water Show 

September sees fewer visitors but plenty of culture

Kids go back to school 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.
Key events: Printers Row Lit Fest, Riot Fest, Chicago Architecture Biennial, Chicago Jazz Festival, Bike the Drive

People ice skating at McCormick Tribune Plaza in Chicago
Outdoor ice skating is all the rage in Chicago in winter © Miune / Shutterstock

The Chicago Marathon gives the city a run for its money in October 

Temperatures drop, averaging 53ºF, and the baseball season is over, but basketball and hockey fill the gap at the end of October. Chicago Bears' games and tailgate parties are still in full swing, while more active types put their energy into the Chicago Marathon.
Key events: Chicago Marathon, Chicago International Film Festival

November is the time for budget travelers 

Temperatures in Chicago drop even further, but November can still be comfortable enough to squeeze in some time outside. The holiday season begins in earnest by the end of the month, bringing a festive mood to the Windy City.
Key events: ZooLights begins at Lincoln Park Zoo

Holiday season is in full swing in December

'Tis the holiday season, and all of Chicago twinkles with good cheer. Michigan Avenue bustles with holiday shoppers and downtown shines with a million twinkling lights. Outdoor ice rinks open and hotel bargains abound, for those brave enough to face the chill.
Key events: Christkindlmarket

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This article was first published February 2021 and updated March 2022

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