When’s The Best Time To Travel Through Chicago?

Written by Simon in Destinations
Image Credits: Pexels.com

Chicago is one of the top destinations in the world. It’s home to some world-renowned sports teams, famous skyscrapers and top-notch Chicago style food. It’s also a very crowded city that boasts more than 2.7 million people are living and walking the busy Chicago streets.

Finding the best time to travel to Chicago to get the most bang for your buck is a question I’ve always had. After some research about the city, here’s what I can tell you.

When’s the best time to travel through Chicago? April and May are two of the best months to travel through Chicago. Also, September and October are great times to travel to Chicago. These months will be warmer and will also help to avoid the busiest times of the year, and lodging prices will be lower.

There is plenty Chicago has to offer and vast amounts of activities and tourist attractions you can elect to visit with the family on a trip to Chicago or even if you are passing through. 

If you stick around for a minute, I’ll break down some must-try activities that you and the entire family can enjoy.

Why April, May, September, and October Make the Most Sense

I mentioned previously that the best months to visit Chicago is during the months listed above. Let’s break this down a little more before moving on. First off, for those who aren’t aware, Chicago is a congested and busy city.

Cars, taxis, and Uber are still out in substantial amounts, but the foot traffic is also very congested. This is the result of 2.7 million individuals living in the city and thousands more coming to visit for various attractions.

During the summer months, Chicago can get extremely packed. It’s known for fantastic festivals, Chicago Cubs baseball games and home of the Chicago Blackhawks. These three items alone draw in many outside visitors.

Traveling with your family during these summer months is not only going to be extremely hot, but it’s going to be hard to do much of anything without long waits and huge amounts of frustration. Especially when moving through the city with the kids.

Let’s chat about the weather for a moment.

Common Weather Patterns in Chicago

In Chicago, individuals will experience frigid cold temperatures in the winter, and in the summer, it gets sweltering hot. The heat mixed with the smell of the city is a not so glamorous or desired combination. Of course, for the 2.7 million who live there, it’s just a part of life.

Here’s a look at the average temperatures based on the time of the year in Chicago.

Summer Months, May - September

  • High temperatures: Average of 85 Degrees F
  • Low Temperatures: Average of 48.5 Degrees F

Spring and Fall Months, and September-November

  • High Temperatures: Average of 62.2 Degrees F
  • Low Temperatures: Average of 43 Degrees F

Winter Months, November- February

  • High Temperatures: Average of 34 Degrees F
  • Low Temperatures: Average of 16 Degrees F

*Source- The National Weather Service Database

As you can see, the months we discussed previously make perfect sense as to why your family would enjoy these times of the year the most when visiting Chicago or passing through. They are about the ideal weather combination.

Not too hot and not too cold.

How Should I Dress for The Weather?

If you are traveling during the times we suggested earlier, you need to dress in at least 1 layer. Chicago is predictable with the weather but in a city like Chicago, it can go from too hot for comfort to slightly brisk at night.

It depends where you are. Take Michigan Avenue for example. During the afternoon hours it may be way too hot for a light jacket, but with the lake breeze blowing in, you may feel the need for jeans and a sweater during the evening and early morning hours.

Pack at least one additional layer when traveling to Chicago.

9 Family Fun Attractions to Try in Chicago

#1 Wrigley Field

Wrigley Field is something you can do with the entire family. Especially in September. The weather will be perfect, and the Chicago Cubs will have plenty of home games to play in September. Take the family out to a ballgame.

Expect the price to range to be about 25.00 USD per adult and 10.00 USD per child for admission. Be sure everyone in the family tries a Chicago style hotdog on this excursion.

#2 Millennium Park

Millennium Park is Chicago’s second most popular thing you can do in Chicago. Millennium Park offers free art museums and often has other festivals taking place that the entire family can enjoy.

The price can range from free up to roughly 100.00 USD per family of 4 depending on what’s happening and what festivals are taking place.

#3 Navy Pier

Navy Pier is the home of some extremely colorful buildings beautiful scenery. It’s not only one of the most popular attractions in Chicago but the entire Midwest of the United States.

There is no shortage of activities that the entire family can enjoy. You could enjoy any of the following excursions with the whole family while visiting Navy Pier. Here is 6 example to giver you a preview or some ideas.

  • Carnival Wheels and Rides
  • The Architecture River Cruise
  • Chicago’s Children’s Museum
  • The Classic Lake Tour
  • Bike Ride Trails
  • The Chicago Theatre

Overall, Navy Pier would fall in the top three things you must do while in Chicago with the family.

#4 Lincoln Park Zoo

One of my favorites on the list. Lincoln Park Zoo is a huge glass dome containing thousands of tree species in addition to tropical plants. You can see everything from ferns to orchids. It’s possible the kids could a get bored depending on their taste but still a free excursion to enjoy with the family.

If you want to step it up to the next level to really bring the kids a thrill, check out number 5 on the list.

#5 Shedd Aquarium

Shedd aquarium houses nearly all freshwater and saltwater fish and just about any ocean animal you can think of. You can see everything from sharks, to whales to beautiful dolphins. The entire family is bound to have a great time on this excursion.

The average cost of this attraction will run roughly 39.00 dollars for adults and kids have free admission.

#6 Michigan Avenue/ Lake Michigan

Michigan Avenue is a long stretch of road and trails designated for walking the beautiful shorelines of one of the most beautiful and largest lakes known to man. It’s free to enjoy this activity. Just make sure to find some parking ahead of time or plan for public transportation.

It’s a very busy area of Chicago regardless of the time of the year that you visit.

It’s a family friendly safe excursion that you can do for free and will be blown away by the views. Not to mention the breeze coming off the lake is something to remember.

#7 The Chicago Architecture Foundation

Chicago doesn’t play around when boasting its abilities to play host to some of the tallest most extravagant buildings in the world. It has the Chicago Architecture Foundation for that purpose alone.

Enjoy boat tours and walking tours that will take you and the entire family on a short trip explaining and detailing some of the best buildings in the city. It’s only 20.00 dollars for adults and children can attend this activity for free. Another cheap getaway for the day the entire family can enjoy.

#8 The Chicago Museum of Science and Industry

This is a must do excursion with the kids and the entire family. It’s the largest museum in the western hemisphere. Even kids enjoy this outing. Another hot-spot in Chicago to see shows on humpback whales and space exploration.

That only scratches the surface of what this museum has to offer. Be sure to give it a try.

It’s only 18.00 USD for adults and the kids will get in for a discounted price.

#9 The Art Institute of Chicago

This is something the whole family can enjoy depending on the children’s ages and interest level in art. The Chicago art museum plays home to some of the most famous art collections and only cost 25.00 dollars for adults. Admission for children is free.

Another must try while passing through Chicago if you ask me.

So, that wraps up 9 things to try with the entire family while in Chicago but what other considerations need to be accounted for? What else do you need to know before traveling to Chicago?

Transportation in Chicago

This is one area where Chicago can be tricky but it’s getting much better. Using your rental vehicle or even a personal vehicle can be stressful, to say the least.

The traffic can be as congested as New York City in some areas. A big plus is that public transportation does excellent if you are traveling with the family. You can use the Metro or L trains or even call a cheap Uber large enough to get your entire family from Point A to Point B.

Transportation is also relatively cheap in Chicago. An Uber or Taxi may run you 7-20.00 dollars to get to your destinations, and metro tickets are 6-15.00 dollars for the family. You shouldn’t have any problems getting around if you play your cards right.

How Much Does Gas Cost in Chicago?

In Chicago, if you are in the heart of the city, the fuel prices will be slightly elevated but still relatively cheap. The average cost per gallon for gasoline in Chicago currently sits at roughly 2.27 per gallon. On the grand scale of gasoline prices, this is cheaper than many other major cities in the United States.

Do Hotels and Dining Cost A Lot in Chicago?

Here’s a look some of the restaurant pricing you may encounter in Chicago.

Again, this depends on where you are. In general, no. Chicago isn’t overly priced for most family restaurants. A family of 4 could enjoy a meal of around 80.00 USD. If, however, you are in areas of Chicago such as Wrigleyville or Downtown Chicago, the price may be much higher.

Your best to stick to the outskirts of the Downtown Chicago area and not eat at a restaurant in Wrigleyville if you are looking for a budget-friendly, quick trip to take with the family. Outside of these areas, you won’t break the bank on meals and dining.

As far as hotels, it depends on where you stay. Hotels are reasonably priced in Chicago. For a family of 4 to stay in Downtown Chicago, you would be looking at roughly 175.00 USD per night. You can surely find it cheaper if you look at the outskirts of the Downtown area.

Beware, however, this may easily cancel out on cost because of the public transportation cost you will pay instead of being within walking distance of all the excursions we discussed previously.

Anything Else I Should Know about Chicago?

As a family traveling to Chicago, the only other thing that needs to be mentioned is to be sure to try the Deep-Dish Pizza at basically any restaurant in the entire city. Chicago is most famous for its pizza, hot dogs and Italian beef. If you have the opportunity, you need to be sure to try each one of them.

You and your family will not be disappointed with this decision. Trust me.

Putting It All Together, Chicago Is A Great Destination for The Entire Family

Chicago has some high-cost excursions and some free family fun attractions that you can enjoy. It’s known for great food and has plenty to offer regardless of your likes and dislikes.

From towering buildings with beautiful designs to the famous Lake Michigan, you can surely find something the whole family will enjoy. Be sure to dress appropriately and figure out transportation methods, and it will be a trip that’s well worth the planning and cost and a trip for the family to remember.

Hello, my name is Simon. I love traveling, and so does my girlfriend. I am an internet entrepreneur and I run my own company, but I have also been working as a tourist guide for a short time - years ago.

We have two kids now, and we want to take them out, to see the world.

As there are a few more obstacles traveling with kids. Follow our travels, reviews, and path to knowledge