Best Time to Visit Chicago: Month-by-Month Guide (+Photos)

Famed for its wonderful architecture and world-class museums, Chicago is one of the most popular cities to visit in the States. Each year, millions come to see its iconic landmarks and experience its vibrant city life.

Set along the shores of Lake Michigan, it sees the vast majority of people visit between April and October. This is when the weather is warmest, the skies are sunny and blue and tons of fun events are going on. The rest of the year, the Windy City is pretty cold and grey with the winter months being particularly brutal.

To help you plan your trip, let’s take a look month-by-month at what the climate, crowds and prices are like in the ‘Heart of America’. We’ll also cover the many festivals and cultural events that take place around the city.

In this post, we’ll cover:

What’s the Weather Like in Chicago?

With temperatures averaging just 30 to 48°F (-1 to 9°C) during the day and often dropping below freezing at night, Chicago’s winters are long, cold and windy. The days are also much shorter between November and March with less sun peeking out from behind its clouds.

Both its spring and autumn are usually short, mild seasons, consisting of April and May and September and October. These count among the best months weatherwise in Chicago with there also being fewer crowds around. In addition, they have either pretty blooming flowers or fiery fall foliage for you to enjoy.

June, July and August are the hottest months of the year when temperatures average 80 to 84°F (27 to 29°C). While it can get a bit humid at times, the climate is usually cooler down by the lake. Despite the days being the longest and sunniest, it does tend to rain a bit more during these months.

Best Months to Visit Chicago


As Chicago is notorious for its bitter winters, its low season lasts from November to March when the wind and cold make spending time outside less pleasant. There is a slight uptick in visitor numbers around the Christmas holidays as people come to enjoy all the lights, decorations and festive ambience.

Although more expensive and crowded, by far the best months to visit Chicago are between April and October. During this period, the warmer temperatures are great for exploring all its interesting neighbourhoods and attractive lakefront. You can even sunbathe, swim or enjoy watersports in July and August when the days are hottest! The city also has a jam-packed calendar of exciting events to take part in with something going on all the time.

Chicago in January

Chicago Winter

The coldest month of the year, January sees temperatures plummet to 14°F (-10°C) at night with the days not being all that much better. While you’ll need to wrap up warm and spend more time in the museums, there are no crowds at any of its attractions. Both its hotel prices and airfares are also very affordable.

Thankfully, some lovely Christmas lights remain up, bringing some much-needed cheer to its short, dark days. Although it is certainly cold outside, it’s worth ambling around Lincoln Park Zoo for its colourful displays.

You can also ice skate at Millennium Park or Winter Wonderfest along Navy Pier. Many museums also offer free admission in January while there are tons of top-class eateries to try out during Chicago Restaurant Week.

Chicago in February

Chicago Auto Show

February is not much better with it often snowing for around 6 or 7 days, though this varies a bit from year to year. The wind is still bitingly cold and the skies above the city are mostly cloudy and grey. On the plus side, it rains very little. You’ll still have to layer up, however, if you plan on spending much time outside.

As it is the low season, accommodation and flights are much cheaper than in summer with its main sites and museums being completely crowd-free. To entice people to shows, various venues offer discounted tickets as part of Chicago Theater Week. Aside from celebrating the Lunar New Year in its Chinatown, you can always attend the Chicago Auto Show; the largest and longest-running event of its kind in the States.

Chicago in March

Chicago in March

As the worst of winter is over and spring is in the air, visitors slowly start to return in March. Averages of 46°F (8°C) are still pretty cold though with amazing ice shards sometimes seen piling up along Lake Michigan’s shores as its ice sheets melt. If you want to visit Millennium Park or the Magnificent Mile, you’ll still need a thick coat to keep out the chilly wind.

The highlight of the month is, of course, St. Patrick’s Day when pub crawls and block parties take place all around town. A huge parade is held and the Chicago River is even dyed green! While prices do start to creep up, they are not as bad as later in the year. Another fun thing to do in March is watch the Chicago Cubs kick off their MLB season at Wrigley Field.

Chicago in April

Chicago April

With temperatures rising to 59°F (15°C), April is the first month of the year that you can comfortably spend time outdoors in Chicago. Besides sauntering along the Magnificent Mile, taking in its sparkly shops and soaring skyscrapers, you can enjoy fantastic boat tours about its river or lake. The flowers are also blooming with its farmers’ markets opening up again.

While it does rain at least a bit for 13 days on average, there is way more sunshine and the days are longer. Except for around the Easter holidays, prices are generally more affordable and its attractions aren’t yet too crowded. Other than walking about Navy Pier or Millennium Park, you can attend events like Comic Con or the Chicago Latino Film Festival.

Chicago in May

Chicago in May

May is even better weatherwise in the Windy City with its crowds and prices also increasing as a result. Average temperatures reach the low 70s (20°C) with there now being around 9 hours of sunshine and 15 of daylight each day. A very lively atmosphere reigns over the city with countless cool cultural events and festivals taking place.

Aside from hiking or cycling along its Lakefront Trail and basking in epic views of its skyline, you can attempt the Chicagoland Spring Marathon. There is also music and food to enjoy at Maifest in Lincoln Park and tasty brews to sample at the Illinois Craft Beer Week. Fun cruises and parties celebrate Cinco de Mayo while the nation’s largest Memorial Day parade goes on too. May feels like the start of summer with everyone outdoors having a great time.

Chicago in June

Chicago in June

As June boasts some of Chicago’s best weather and biggest events, it is a very popular time to visit. Although it does rain for roughly 10 days on average, its showers are usually short and quickly give way to resplendent sunshine. Temperatures hit 80°F (27°C) with many now relaxing at its parks or kayaking, windsurfing and sailing out on the lake.

Prices are higher with its main sites and museums all packed. Its innumerable events more than make up for this, however. Beside its famous Chicago Blues Festival, colourful parties, parades and events are held for Pride. The Millennium Park Summer Music Series also starts as does the ten-week-long Grant Park Music Festival. If that wasn’t enough, Navy Pier puts on free spectacular fireworks shows each Wednesday and Saturday night from Memorial Day weekend until Labour Day weekend in September. Phew!

Chicago in July

Chicago Beach

Absolute peak season arrives in July when all its hotels and restaurants are full and massive crowds throng about must-see sites like The Bean and Buckingham Fountain. While Chicago is rather hot and humid – averaging 84°F (27°C) – you can now sunbathe and swim at North Avenue Beach. Navy Pier’s shops, gardens and carnival rides will all be heaving, however.

Although airfares and accommodation are much more expensive in summer, the marvelous weather is perfect for being outdoors and enjoying all its exciting events. Aside from taking boat tours along the Chicago River, there are the Pitchfork and Square Roots music festivals to enjoy. Fabulous fireworks shows are also held for the 4th of July. It does still rain quite a bit though so make sure to pack a mix of clothes when you visit.

Chicago in August

Chicago Riverwalk

As the weather is hot, the days are long and the skies are sunny and blue, August is just as popular a month to visit Chicago. While it still rains a decent amount – the most of the year along with June and July – its short, sharp showers are quickly over. This shouldn’t stop you though from lounging on its attractive beaches or cycling along the scenic Lakefront Trail.

With so many people visiting in summer, prices remain high with queues forming at its main museums and attractions. You’ll want to book tickets to the Skydeck Chicago or 360 Chicago Observation Deck in advance if you don’t want to miss out on their unbelievable views.

Lots of great events take place too with Lollapalooza and its Chicago Jazz Festival both attracting enormous crowds. In addition, you can watch heart-stopping stunts by daredevil pilots and boat-jumping pros at the Chicago Air and Water Show.

Chicago in September

Chicago in September

While the summertime has so much for you to see and do, most people consider September to be the best month of the year in Chicago. This is because the weather is cooler, the prices are cheaper and there are fewer crowds around. Averages of around 75°F (24°C) are more comfortable for strolling along the Magnificent Mile or around Millennium Park.

Although the Summer Music Series, the Grant Park Music Festival and the fireworks at Navy Pier are now over, there are plenty of other interesting things going on. These include not just its Riot Fest and World Music festivals but the Taste of Chicago too – the largest food festival in the world. Big celebrations are also held for Labor Day and Oktoberfest. You can also watch the Chicago Bears play in the NFL and swim in the lake while it’s warm enough.

Chicago in October

Chicago Autumn

October is also an ideal time to visit as the temperatures are mild and there is less rain. The autumn leaves also look amazing in its parks and down by the lakefront. While you can still kayak, sail and take boat trips about its picturesque waterways, you’ll probably need to start taking a jacket around with you. The days are also shorter and there is less sunshine.

As the summer crowds have headed home, prices are more affordable again and there are fewer visitors to top attractions like the Art Institute of Chicago and Shedd Aquarium. Aside from running the Chicago Marathon, you can check out cool screenings at its International Film Festival. Numerous parties are also held for Halloween. As the NBA season starts again, you can always watch the Chicago Bulls play an action-packed game at the United Center.

Chicago in November

Chicago November

With the weather growing colder and the wind picking up, November sees a massive drop in visitor numbers to Chicago. While there are now just 4 hours of sunshine and 10 hours of daylight a day, you won’t have to jostle for space at its must-see sights. You’ll want to spend more time at its museums as averages of 48°F (9°C) aren’t great for walking around in.

Hotels and airfares are much cheaper until around the middle of the month when things pick up again a bit. This is when colourful lights and decorations are put up along the Magnificent Mile, around Navy Pier and the Lincoln Park Zoo. Christmas markets and winter festivals are set up in various squares around town. To top it off, a large parade is held for Thanksgiving along its legendary State Street.

Chicago in December

Chicago ice rink

Despite December being brutally cold, windy and dark, plenty of people still visit Chicago for all its cheery Christmas festivities. Prices rise around the holidays with the Christkindlmarkt at Daley Plaza and Winter Wonderfest at Navy Pier being pretty busy. Snow sometimes falls with some locals and tourists heading to nearby Wisconsin to hit its slopes.

Often dropping below freezing at night, its low averages of 35°F (2°C) feel much colder due to its biting winds. Plan to spend more time at its museums or wrap up warm when you’re out and about exploring the city. You can also ice skate about the rink at Millennium Park or watch special holiday performances of A Christmas Carol at the Goodman Theater. For New Year’s Eve, spectacular fireworks shows light up the city’s skyline and lovely lakefront.

Leave a Reply

Your email address will not be published. Required fields are marked *