6 Things to Do When You Travel to Chicago This Fall

Fly Privately When You Travel to ChicagoPhoto:Lance Anderson

Deciding to travel to Chicago any time of year can be rewarding, but it’s especially incredible in the Fall.

This is a city that welcomes you in a full embrace from the moment you arrive – just as if you belong here.

Get whisked away by the hustle and bustle of the city. Dine on some wonderful deep-dish pizza. Take a tour of Al Capone’s secret basements. Slip away to Navy Pier.

There is something for everyone in Chicago. And, it’s a city that you can travel to with your spouse, your whole family, or even alone.

So, take a break from your life right now. Book yourself on a private jet charter to Chicago – the windy city – and all that it has to offer you during the fall months.



What Is The Weather Like In Chicago During Fall?

If you are not from the Midwest, then you may not know what to expect when it comes to fall weather in Chicago.

Truth be told, residents of the city don’t even know what to expect. The weather tends to generally be a bit spastic during this time of year. Summer is not wanting to let go and winter has not quite found a firm grip.

When you travel to Chicago in the months of fall, you will get some enjoyable weather no matter the temperature. Typically, you will find the days to be warmer in September and cooling down as you get into November.

Here are the city’s average temperatures:

SeptemberMid-70’s during the day, falling to the low 60’s at night.

October: Mid- to low-60’s during the day, dipping down to low 50’s at night.

November: Temps in the upper 40’s during the day and high 30’s at night.

Depending on when you visit, you should still be able to enjoy the outdoor attractions around the city.

Of course, you may need to dress in warm layers.



10 Facts About Chicago

Chicago is a huge city.

It has a rich history and has nearly 3 million residents to make new history. While the city can entice you to visit on its own, we’ve got 10 fun facts to further justify why you should travel to Chicago.

  • Chicago is home to Lincoln Park Zoo – and it is
  • Chicago is famous for inventions, such as roller skates, spray paint, zippers, skyscrapers, and twinkies.
  • Chicago is a popular tourist destination – receiving over 45 million visitors every single year.
  • Coming in second to the Louvre in Paris, the Art Institute of Chicago has the largest collection of Impressionist paintings in the world.
  • Hot dog stands are booming in this city – over 2,000 of them can be found along city streets.
  • The infamous Route 66 begins in Chicago.
  • The world’s longest continuous street –23.5 miles – is Western Avenue located in Chicago.
  • The Chicago River is the only one in the world that flows backward.
  • After the Great Chicago Fire, the Chicago Public Library operated in an old iron water tank with books donated from around the world.

Ready to pack your bags yet? Ok, maybe you need to see how Chicago celebrates fall before deciding to travel to this amazing city.



How to Celebrate Fall When You Travel to Chicago

Welcoming the new fall season in Chicago is wonderful. The trees start changing and fall foliage brings a golden glow to the city.

Because the cooler, less humid weather is starting to arrive – and the massive amounts of tourists are starting to leave – fall brings a great opportunity for people to get out and enjoy all that the city has to offer.

During this time, you will see many people partaking in outdoor events, such as bird watching, apple picking, and discovering how to get out of a real-life corn maze! But that is not all. Visits to the farms, pumpkin patches, and such are also common festivities.

For those not wanting to leave the city streets, there are a few events that Chicago is anticipating this fall.

The Navy Pier Food and History Tour is something you may not want to miss. This event features 5-star versions of Chicago’s finest food creations all in an effort to prove that Chicago has the best food in the world. And, when your belly is full, the Chicago Humanities Festival can give you something to think about.

As for holidays, Chicago is planning on ringing in Halloween with its Arts in the Dark parade. This parade includes some spooky performers, floats, puppets, and so forth.

If you visit closer to Thanksgiving, Chicago offers you some fun and exciting sites in a parade that has been voted one of the best. The McDonald’s Thanksgiving Day Parade is spectacular – and over the top.



What To Do While You Are Here

Other than seasonal fall activities, what is there to do in Chicago that will make your visit worthwhile?

The question you should be asking yourself is what isn’t there to do?

When you travel to Chicago, it is always full of fun things to see and do – no matter who you are.


1. Indoor Activities

If you are searching for something to do indoors while visiting the Windy City, try one or all of these options:

  • Visit the John Hancock Center if you aren’t afraid of heights. You can visit the sky deck on the 94th floor – known as 360 Chicago – for an unforgettable view.
  • Visit Shedd Aquarium, one of the largest in the world.
  • Check out the Museum of Science and Industry.
  • Plan a visit to Adler Planetarium.

Of course, food is a big thing in Chicago, so you’ll always want to spend time dining at some of the city’s most popular hot spots.


2. Outdoor Activities

It’s fall – so you want to be outdoors. Well, Chicago has you covered with a ton of things to do.

  • Wander through the downtown Farmers Markets for some sweet seasonal treats.
  • Check out Millennium See the Cloud Gate and discover art throughout.
  • Visit Buckingham Fountain in Grant Park.
  • Spend time at Navy Pier.
  • Walk Chicago’s Lakefront Trail along Lake Michigan.
  • Go shopping along The Magnificent Mile.



Start your fall season off right with a trip to Chicago. You will discover a city rich in history, art, and culture. And, it likely won’t be the last time you travel to Chicago, it seems to always call you back again.

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