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Best Time to Visit Chicago | When to Go & Travel Tips

Best Time to Visit Chicago | When to Go & Travel Tips

Looking forward to a trip to Chicago? It’s a good idea to find some key information before planning your journey. Knowing the best, most affordable, and least busy times to travel can help you plan the perfect visit to the Windy City.

Chicago has so much to offer its tourists. From incredible sights to Chicago’s rich history, everyone will find something to enjoy. You won’t want to miss any of it.

That’s why it’s important to plan accordingly, and we’re here to help you out. Check our helpful tips for the best time to visit Chicago so that you come home with memories to cherish for a lifetime, rather than a headache.

After all, there are many things such as weather and timing to take into consideration when planning. Yes, it can be overwhelming. But don’t worry — we’ve done the hard work for you.

We’ll also let you know the worst time to plan your stay so that you can be sure to catch this city at the height of its potential. Trust us, it’ll be worth your time to do your research and get the most out of your trip.

Why You Should Visit Chicago

Bean in Millenium Park pictured in an evening during the best time to visit Chicago

Luis Boucault/Shutterstock

Chicago is worth the visit just for its incredible scenery. The skyline and waterfront views are breathtaking. It is home to some of the nation’s oldest skyscrapers and earliest architecture.

The city’s skyline is among the most iconic and features the Willis Tower, one of America’s tallest structures. History buffs will love to take a tour of the city on a river cruise.

But if outdoor activities aren’t your thing, why not stop by a museum? There are dozens of museums in Chicago and the surrounding area. Artists and creative types will also find plenty to do, including live shows and festivals.

Spending an afternoon at The Art Institute of Chicago is also a favorite. Check their website to find out what exhibitions might be happening there during your stay. If you prefer live entertainment, there are several Broadway theaters to attend in Chicago.

After a long day exploring, don’t skip the cuisine. Whether you’re a foodie, or just really hungry, Chicago definitely won’t let you down. The food culture here is sure to impress any picky eater.

Try a slice of the deep-dish pizza the city is famous for or a good old Chicago-style hotdog. Brownies, perhaps the best-baked treat in America, were invented in Chicago. Pick one up on your way back to your hotel at one of the town’s excellent bakeries.

Best Overall Time to Visit Chicago

Riverwalk pictured during the overall best time to visit Chicago

Sean Pavone/Shutterstock

Overall, the best time to visit Chicago is in late April through May or September through October. Late spring is a great time to enjoy this enchanting city.

With temperatures starting to rise, May will often see days of over 70 degrees. In September and October, you can also count on fair weather. Temperatures usually remain above 60 degrees well into the fall.

Kids are in school for most of these months, which can be a game-changer when visiting the city. You’ll be able to take advantage of the many parks and gardens that promise to be gorgeous in both the spring and autumn seasons. 

The sweltering summer months tend to be overcrowded. Temperatures in July average 85 degrees, and that’s made worse in the city with busy streets and cramped sidewalks.

Vacationing families, photo-happy tourists, and students on summer break can make Chicago feel chaotic and uncomfortable. While there is plenty to do, anticipate dodging strollers and sprinting children. 

If you’re worried about missing out on themed events that usually happen in summer, don’t sweat it. There are some great festivals to check out in both the fall and spring.

The cool air and beautiful foliage make the perfect backdrop to any outing. There are a lot of haunted tours and autumn celebrations offered in October. They’re a great way to take in some of the city’s incredible history.  

Cheapest Time to Visit Chicago

Ice on the Chicago river pictured during February, the cheapest time to visit

marchello74/Shutterstock

If you have a tight budget, the cheapest times to visit are in January and February. Like many other places, the Windy City experiences a decline in revenue and tourism in the winter months following the holidays.

This increases the likelihood of finding great deals, including flights and hotel stays. If you want to take advantage of these opportunities, it is best to try to book your flight between one and three months before your trip.

Some airlines offer up to 25 percent off, but booking too late could mean missing your chance. Choosing a hotel room at the right time can also make a huge difference in how much your trip can cost.

Try to book your room within a few weeks of your stay. Hotels want to ensure full rooms each night. This means evaluating how busy it is likely to be while in Chicago.

Try to book as close to your arrival date as possible. While scoping out the best deals during your stay, be prepared for cold weather.

Chicago is deep into winter during these months, so you do run the risk of delays and cancellations. With this in mind, it can be a worthwhile trip if you don’t mind a little snow. Just keep calm, pack your boots, and leave early.

Least Busy Time to Visit Chicago

Chicago street pictured during the least busy time to visit with empty streets

MaxyM/Shutterstock

January through April is generally the slowest season for Chicago. If you’re interested in spending some alone time with the city and getting to know its local attractions, you’ll want to stop by during the least busy season.

This will allow you to take your time as you wander. It should come as no surprise that the least busy time to visit Chicago is when families live their day-to-day lives. Kids are still in school at this time of year, and cold weather keeps people indoors.

The average temperature in January falls to a brisk 31 degrees. This allows for a unique perspective when traveling, as it will give you a chance to see the town as the locals see it.

Visit museums and other popular attractions during this time to get their full effect. The same rules apply when hunting for bargains on flights and hotel rooms during this time of year. Try to book flights early to get the best deals.

Once spring settles in and people start traveling again, you can count on prices jumping as much as one hundred dollars a ticket if you try booking less than a few weeks out.

Worst Time to Visit Chicago

Worst time to visit Chicago symbolized by a photo of Lake Michigan with lots of fog and snow

Marchello74/Shutterstock

The worst time to visit Chicago is in the winter months, January through March, with February and March being the absolute worst. According to the locals, it can be especially hard to get past the cold weather during this time.

Although the Windy City may not be the windiest place in  America, it still lives up to its nickname. If you do choose to travel, make sure to wear layers and pack a few extras, just in case.

February through March tend to be unpredictable because they offer few incentives to travel. Deals on flights will be hard to find during these months, and you run the risk of not reaching your destination in time.

Flying through stormy skies might be more trouble than they’re worth if you have your flight canceled altogether. Plus, you’ll have a tougher time finding things to do.

Chicago hosts a lot of festivals, conventions, and the like, but those are a far-off dream during this frigid season. The attractions that draw crowds of tourists will begin later in the year, starting in late spring.

If you want to see Chicago through the eyes of a true local, this is the time to stop by. If you choose to come to Chicago during these months, it’s important to be prepared.

There are tricks to get good deals on flights, such as booking a layover or landing somewhere other than O’Hare (called skip-hopping). But that’s a topic for another article.

Things to Consider

  • Chicago is a wonderful city, no matter what time of year you visit. It is a great idea to plan for your ideal vacation, but don’t get too hung up on when to go. There are indoor and outdoor attractions to explore year-round. So if the weather doesn’t cooperate upon arrival, you won’t be left out to dry. There’s still plenty to do.
  • Be mindful of the seasons. In the middle of summer, there is a lot of traffic between all the locals on school break and tourists flocking to the city. The holiday season will be overwhelming as well, but if you are a fan of incredible holiday displays, it might be worth it.
  • Educate yourself before your arrival. Chicago is a city, so if you’re not from a city, learn how to move and behave in one. Try not to stand in the middle of the sidewalk, don’t swing your purse around, and generally just be aware of where you are. If you can, try to travel with someone that knows Chicago or is at least familiar with navigating a city. 
  • Ask about discounts before and during your trip. Hotels and airlines will sometimes upgrade your service for free or at a great rate if they know they aren’t going to fill a seat or room. Memberships with your favorite hotel chains and restaurants can also be especially helpful if you travel frequently.
  • Check the forecast before you leave. The Windy City experiences all four seasons and often experiences flooding rains and snow that can make it difficult to get around town. These things don’t make it impossible to enjoy your time in the city, but make sure you bring the right clothing and shoes. 
  • Ask around about local favorites. Too often we get bogged down in overly-glamorized attractions for tourists and fail to experience the city itself. Check local social media and ask the concierge of your hotel what their favorite place to get pizza is. You’ll be much more likely to find hidden gems this way than with an internet search of trendy bars in the area.

Frequently Asked Questions

Pretty view of the Chicago skyline in the fall, one of the best times to visit Chicago

Nejdet Duzen/Shutterstock

Still have some questions about the best time to visit Chicago? Check the answers to some common questions below.

When is the best time to visit Chicago Botanic Garden?

Spring is generally considered the “best” time to visit the garden, but there’s always a reason to go. May through early June is sure to be a riot of color as the flowers bloom, so if you want the full outdoor experience, plan a trip in the spring.

Don’t skip the garden if you’re visiting in the fall or winter, however. The fall change is magical and there are some great displays you can check out during the holidays.

When is the best time to see fall colors in Chicago?

If you decide to take your trip in the fall, you’re most likely to see the best colors in early to mid-October, and you won’t want to miss them.

The first two weeks of October are when changing leaves and fall blooms reach their peak. Warm temperatures and an increase in moisture lend themselves to a stunning autumn experience.

When is the best time to visit Skydeck Chicago?

Standing on The Ledge of Skydeck Chicago is an experience many would argue is an essential stop on your agenda. The Ledge is part of the Willis Tower, located on the 103rd floor of the building.

The best time to look out over the city from 1,353 feet up is at sunrise or sunset, but there’s no such thing as a “bad” time for this activity. Twinkling evening views of the city below are also quite breathtaking. 

How many days do you need in Chicago?

If you’re short on time, you can still see and do plenty in Chicago in as few as three days. Most attractions don’t take more than a few hours to complete, so you can plan for several per day.

Many people say that an itinerary of four to five days is the perfect amount of time to get to know the city. Chicago is a great choice for those with only a few vacation days to work with.

When is the best time to move to Chicago?

If you have already taken the dive and fallen in love with Chicago, perhaps you’ve decided to become a permanent resident of the city. Moving into the city is simpler at certain times than others, so try to time your search accordingly.

In May and August, college students are usually shuffling around their living situations, driving up competition. To get the best deals and the least traffic, consider moving during a slump, such as January or February.

So, What’s the Best Time to Visit Chicago?

After all that research, we determined that the absolute best time to visit Chicago is in the late spring or early fall.

These times of year offer the most in terms of activities, the best weather, and the fewest crowds. If you want an ideal trip to Chicago, plan for May, June, September, or October. You will not be disappointed!