Famous for its icy winters, steamy summers and busy festival calendar, Chicago has something going on in every season. The Windy City changes mood with each passing month, but some things are constant – the city’s lively nightlife, cultured museums and animated neighborhoods warrant a visit at any time of year.
Events such as Lollapalooza and the Chicago Blues Festival have put the city on the national festival map, but events fill every month of the year, from championship sports to special museum openings, cultural fairs and community festivals.
Chicago shines in the summertime, with hot, humid days but plenty of lakeshore beaches and parks where you can catch the breeze. The calmer spring and fall have their own charm, and winter sees lower tourist numbers and plenty of snow and ice along the lakefront, adding to the holiday magic.
If you’re looking for a city break with phenomenal art and architecture, truly globe-trotting cuisine and exuberant festivals, Chicago will keep you busy at any time of year. Here’s our guide to the top times to visit the Windy City.
November to April is the best time to score bargain rates
Although Chicago’s winter temperatures hover around freezing point, the bitter wind blowing in off the lake can knock several dozen degrees off the highs due to the wind chill effect. Trees and bushes along the lakeshore become encrusted in ice and plumes of steam rise over the skyscrapers.
But while the chilly temperatures scare many tourists away, bargains abound, particularly for accommodation. Travelers will have their pick of the deals at hotels across the city throughout the winter months, and 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, plus holiday markets and outdoor ice-skating rinks. The icy scenes along the lakeshore add some extra Chicago magic. 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.
Michigan Avenue 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 form your own opinion on the city’s feud with the New York-style pizza pie.
January is Chicago’s coldest month, with temperatures dipping as low as 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.
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 Theatre 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. 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.
As spring 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 Guaranteed Rate Field for the opening of the baseball season.
May and September to October are times to enjoy culture without the crowds
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 museums.
Temperatures are a manageable 50ºF to 70ºF degrees, and there’s a buoyant mood in the city, although rain is often part of the forecast. Budget travelers can find good deals on airfares and hotel rooms, but keep an eye on the calendar; 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 at the end of the month over the Memorial Day weekend and hotels see a rising number of travelers checking in. The better weather means a big turnout in the streets for community-focused festivals such as Mole de Mayo and 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, with the Chicago Jazz Festival, Riot Fest and the opening of the Chicago Architecture Biennial lighting up the city.
Temperatures drop even further in October, averaging 53ºF, and the baseball season is over, but basketball and hockey fill the gap at the end of the month. Chicago Bears games and tailgate parties are still in full swing, while more active types put their energy into the Chicago Marathon.
June to August is the time for festivals, beaches and baseball
Warm weather and a packed festival calendar make summer the peak time to visit Chicago. When 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. The temperature creeps towards 80ºF, but it rains on a third of the days. That doesn’t deter the people from partying during Chicago’s spirited pride celebrations.
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. Make the most of the city’s many parks – art-filled Millennium Park marks the start of a chain of parklands running south from downtown, following the banks of 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 has concerts downtown nightly, Taste of Chicago attracts visitors from all around the world, and fireflies glow everywhere. It can be 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).
This article was first published Feb 23, 2021 and updated Aug 10, 2024.