When Is the Best Time of Year to Visit Chicago?

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Illinois received 120 million visitors in 2019 (the last pre-pandemic year!), with Chicago responsible for a little under half of those tourists.

Chicago is the third biggest city in the US and has a prime geographical location close to the Canadian border in the midwest. If you’re seeking a fun weekend break, this city has a lot to offer no matter when you visit.

But are there better times to take a trip to Chicago than others? What is the best time of year to visit Chicago? This is a month-by-month guide listing all the pros and cons so you can find the best time to visit Chicago for you!

January

If you know anything about Chicago, you know that it experiences four distinct seasons. Spring is mild and fresh, summer is warm and sunny, fall is crisp and brisk, and winter is cold. And yes, it does tend to snow.

January experiences highs of 32°F and lows of 20°F. It’s pretty cold, but there are some pros to visiting Chicago in January.

It’s less crowded, and hotels and entertainment are cheaper in the off-season too. There are still many things to do in Chicago in January, like the light show at Chicago Botanic Garden and the ice rink in Millennium Park.

February

February’s temperature is a little milder than January, with highs of 35°F and lows of 25°F. There is also a higher chance of snowfall in February.

Since February is also off-season, it boasts the same cheap hotel and entertainment prices as January. Plus, Chicago Theater Week is in February, so you’ll enjoy even cheaper tickets and over 100 shows to choose from. It’s, without a doubt, the best time of year to visit Chicago for theater fans.

March

Street signs are starting to thaw out, and the flower buds burst open. March experiences balmy highs of 45°F and lows of 35°F. Okay, you can put those tank tops back in the drawer.

But plenty is happening in the city that could make March the best time of year to visit Chicago for you. This city goes all out for its St Patrick’s Day celebrations with not one, not two, but three parades. Chicago Restaurant Week in March also offers visitors tons of dining deals so you can splash out on a fancy meal or glam brunch cruise.

April

With the arrival of April comes the start of Chicago’s shoulder season with highs of 55°F, lows of 43°F, and a higher chance of rain. But don’t worry, Chicago has tons of great museums (like the Art Institute) where you can hide from bad weather.

The Chicago Cubs opener is also around April time, and the team celebrates by letting off fireworks. If you’re lucky, you might beat the odds and score a couple of game tickets!

May

May enjoys highs of 65°F and lows of 54°F. Hotel prices are starting to climb, but they will be nowhere near the eye-watering prices of summer.

This month, Chicago’s events calendar bursts with no less than 20 art festivals, music festivals, and markets. It’s the perfect time to get away for a romantic break before the end of the school term.

June

You can take your tank tops back out again because June in Chicago has highs of 77°F and lows of 63°F but keep in mind that it is also the rainiest month. Millennium Park is where it’s at in June, thanks to its music and film festivals. Chicago also goes all out for Pride month with one of the largest parades in the world.

July

July is one of the most expensive months in Chicago for hotel prices, but it also has the hottest temperatures. Chicago has highs of 83°F and lows of 70°F this month. Lollapalooza in Chicago’s Grant Park also makes the city even more crowded and expensive than it already would have been in summer.

August

Highs of 80°F and lows of 70°F mean August is still a warm, sunny month in Chicago. The city’s outdoor events are still rocking with free events like Chicago Summerdance and Grant Park Music Festival. It’s a great time to bring your kids since the weather is great and there is so much to do outside.

September

The weather is starting to turn with highs of 73°F and lows of 63°F, but Chicago isn’t slowing down yet. All the summer music and arts festivals continue into September. The Roscoe Village Burger Fest and Chicago Gourmet food festival are perfect for visiting foodies.

October

Do you love seeing the leaves change color on the trees? Chicago offers highs of 63°F and lows of 50°F in October, which means it’s mild enough to walk around the city and enjoy the scenery. You can also admire the scenery while running the Chicago Marathon, which happens every October.

November

Not going to lie. November’s weather is a little miserable. It’s cold (highs of 50°F and lows of 40°F) but doesn’t offer any picturesque snow and very few festive events. But you can enjoy cheaper hotel rooms, museums, and their Thanksgiving Day parade.

December

Like all big cities in the US, Chicago goes all out for the holiday season. And with highs of 37°F and lows of 27°F, Chicago offers a good chance of a white Christmas. You can enjoy Winterland at Gallagher Park, Christkindlmarket, and ice skating is back at Millenium Park.

So, When Is the Best Time of Year to Visit Chicago for You?

There is no “one” best time of year to visit Chicago. There are tons of reasons to visit year-round. But now, you can use this guide to choose the month that offers the best weather, entertainment, and deals for you.

You might know when you’re visiting Chicago, but you’ll need other Chicago travel tips so you can organize the rest of your trip! Check out the travel section on our website for all the expert advice you’ll need planning a trip.

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