When is the Best Time to Visit Chicago – 2024 Travel Guide

Chicago might be one of the most interesting cities you can visit when you are in that certain area. Sure, Wisconsin, Milwaukee, and Indianapolis might seem like great contenders, but none of those can compare with Chicago. It seems like this beautiful city offers tourist attractions for all kinds of people.

However, you are probably well aware of how the weather can get in the northern parts of the US. Wisconsin and Illinois can get especially cold during autumn and winter. If you are the type of person that cannot endure a lot of cold, we wouldn’t recommend going during those two seasons. If you do not have a problem enduring below 30 degrees temperatures then you should definitely visit Chicago during those two seasons. The snow makes it especially beautiful.

Assuming that you want everything to go perfect while visiting Chicago, you will need to do a bit of research to find out which exact month is the best time to do this kind of traveling. With this 2024 travel guide, you can easily decide what time of the year you should fly to this amazing city.

Best weather

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Most people like to travel during spring or autumn because that is the time of the year when the temperatures are most balanced. It is not too cold, but it isn’t too hot either. No one likes to bake under the sun for hours and hours while walking down the streets, exploring all of those amazing tourist attractions.

If you are one of those people that want to travel in the best possible weather then we would recommend visiting Chicago early or late spring. March and April can still be a bit colder and there still might be some snow, but May or June is definitely the perfect option. The temperatures will not drop below 50 and they will never go above 77.
We would recommend that you grab an umbrella because May can have several rainy days.

Cheapest season

While the idea of walking down the streets of Chicago during spring or summer might seem like a great idea, the pricing will not seem so fun. Almost everything will be twice as expensive when compared to the winter season. Most people do favor good weather which means that everything is going traveling during springtime.

If you truly want to save a lot of money when visiting this place, your best option is the winter season. Most of the tourists will probably leave during October or November. This means that hotels and flights will be half the price. Hotels will not expect any guests during this season which means you will be able to grab a big room for a fraction of the original cost.

I would recommend avoiding December because people are much more active throughout the city because of Christmas and New Year’s Eve. During December, everyone will be running around shops and malls trying to buy Christmas decorations and gifts. You won’t be able to do any kind of peaceful shopping. This is why I believe that January or February is the best time to visit this place. Most people will be stuck at home or at work while you get to do anything you want.

If you truly want to save cash while visiting this place, you should check out coolthingschicago and see their reviews of the best hotels that you can find in Chicago.

Family holiday

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For the people that are planning to travel to this city with their family, I would recommend them to consider the summer season. Sure, it might be a bit hot throughout the day, but it is definitely worth it. In fact, the summer days in Chicago are pretty mild, so you won’t have to worry about the weather getting too hot.

I believe that the summer days are best for those that want to travel to this city with their family because the days are much longer, giving you the chance for a lot more activities. Most kids will be out of school too which is important. Kids will love to go swimming at the South Shore Beach while the parents go on a fancy brunch at the nearby restaurants.

Keep in mind that the summer days can be a lot busier because most tourists like to check out this city during this season. The pricing will also be a bit higher than what you would expect.

For Food Lovers

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For the people that love to taste the food of other cultures’, you will definitely fall in love with Chicago, especially during summer. The entire city has had influence from many countries around the world. You will not have trouble finding Chinese, Indian or European restaurants.

What’s even more amazing is the fact that there are a couple of festivals during the summer that are entirely focused on food. For example, the Taste of Chicago that is held in July is the world’s largest food festival that lasts for about five days. During this festival, you will be able to see everything. Whether you want to see certain music artists, do some dancing or taste foods that you have never seen in your life, there is basically everything you can do during this festival.

Assuming that you won’t be able to get a plane ticket to Chicago in July, you should consider getting a flight in September. Chicago Gourmet is held in September which is another great food festival that you definitely have to see. This one lasts about three days, but it still more than enough to see and taste all kinds of things.


The reality is that Chicago never sleeps. It is always alive and you will be able to see the things you want to in any season. Of course, some might be cheaper and others might be more pleasant, but you can still have a good time during the winter or autumn.

However, if you truly want to have the perfect holiday while you are in Chicago then you should definitely visit this beautiful city during the seasons we mentioned.

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