When is the Best Time to Visit Chicago
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When is the Best Time to Visit Chicago?

There’s truly never a bad time to go to Chicago. Each season in the city offers something wonderful, from renowned festivals to snow-capped parks. But, if you want the best travel rates and to steer clear of the crowds, knowing when the best time to visit Chicago is will work in your favor.

Of course, each traveler’s “best time to visit Chicago” will vary based on their travel preferences, budgets, and schedule.

To help you plan your Chicago excursion, decide which element of a vacation is most important to you:


For weather like this, find out when the best time to visit Chicago is

Which Season has the Best Weather?

Although each season has its pros and cons, those looking for mild temperatures and sunshine will have the best luck in the spring and fall. The months of late April, May, June, September, and October typically have temperatures ranging from the mid-50s to high-70s.



Do know the early summer months can be a bit rainy, so pack appropriately!

Summer in Chicago tends to be quite hot, with average temperatures reaching well into the high 80s and 90s. And, while the winter months can be harsh, seeing the city covered in snow is a memorable sight. That is if you can handle the freezing temperatures.

Looking for discounts? The best time to visit Chicago is on the off-season.

When Should I Go for Great Discounts?

City vacations can be expensive. Between transportation costs and hotel rates, the foundations of a trip can demolish a travel budget if not monitored.

That said, the best time to visit Chicago for those on a budget is during the winter. During late November and early December, along with the entire months of January and February, flight and hotel rates plummet. Meaning you can take advantage of deep discounts on all aspects of your vacation.

Since most travelers are escaping to warmer destinations in the winter, Chicago needs to compete with lower rates. If you can brave the cold in favor of incredible rates, there’s no better time to go to Chicago.

Although, no matter when you choose to visit Chicago, you can always discover great savings when you bundle your attraction and show tickets with a hotel.

What Time of Year is Ideal for Families?

Are you planning to bring your kids along for the ride? If so, try visiting Chicago in the summer.

On top of being easier to schedule around the school year, there is plenty to do for kids in Chicago during this time of year. Visit Navy Pier, go to the beach, explore Millennium Park; your options are endless.

Do know that this is also the most expensive and crowded time of the year. Other families are following your lead and visiting while school is not in session. However, with a bit of advanced planning, you can book your hotel and activities ahead of time and find huge discounts.

And, everyone knows summer vacations are stressful for parents. To help you out, we’ve compiled a guide full of travel tips for your Chicago family trip!

If visiting Chicago during the summer isn’t feasible, don’t worry. Kids will love the city any time of year!

Crowds view the Cloud Gate structure at Millennium Park. Avoid the crowds by finding the best time to visit Chicago.

Which Season has the Fewest Crowds?

I get it. I’m not a fan of crowds either. I’m the crazy person dodging in and out of crowds trying to get to my destination.

If you’re the same way, avoid visiting Chicago during the summer months when all the other tourists flock to the city. Instead, the best time to visit Chicago is in the spring and fall.

In addition to the pristine weather, you’ll enjoy fewer crowds at top attractions and destinations like:

Plus, these seasons often have discounts on tours and attractions to entice people to visit! However, these attractions may have reduced hours during the “off-season.” Remember to double check the hours of operation before you go.

Visitors watch a concert in Millennium Park in Chicago

When are the Top Events in Chicago?

Chicago is home to a variety of events all year long. Many of these events are world-renowned festivals, culinary events, and infamous concerts. A few of the top events include:

Have a specific Chicago festival you’d like to attend? Find out when it is and start planning your trip!

For views like this, discover when the best time to visit Chicago is

When is the Best Time to Visit Chicago?

For low travel prices, excellent weather, and an abundance of events and things to do, the best time to visit Chicago is:

Spring and fall.

Both seasons boast perfect weather and manageable city crowds, meaning you’ll enjoy a carefree vacation in the Windy City.

So, when are you headed to Chicago? Tell us about your plans!

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