Museums, Skyscrapers, Sports & More – Chicago, Illinois

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Chicago, the Windy City, lies along the shimmering west coast of Lake Michigan.  Best known for its towering skyline, deep dish pizza and bitterly cold winters, the city is the third largest in the United States.   Numerous trade associations hold annual meetings here every year, so I expect a lot of families accompany conventioneers and seek something to do while the conventions are taking place.

Such a large population center means that there should be a TON of cool things to do, and Chicago delivers.  The challenge for me as your Totally Teen Travel tour guide is to NARROW down the possibilities.  Unless you actually MOVE to Chicago, there is plenty for everyone to do during any given time spent here!  Even locals might argue they’ll never get around to everything!

Segway tour of Chicago
Multiple Segway tour companies

Unlike most cities about which I’ve written, there are multiple appealing attractions and things to do within their own type of category.  For example, Chicago has dozens of compelling world-class museums you can visit.  How the heck do you narrow the list down?  And who doesn’t want to experience the amazing Chicago skyline?  Which viewing opportunities are the most intense?  And how to best get into the sports the Windy City is so famous for?


What I will do here is recommend the most teen-friendly attractions in these categories.  But I suggest you go a step further and research ALL the exciting possibilities available to travelers on Chicago’s online visitors’ bureau.  Scroll down a bit and on the right side of the page you can “create a personalized itinerary” via the Utrip Trip Planner.  Input the requested information and voila!  Recommendations based on time of year, budget, age of participants and more are provided.

Why not save some serious coin while you enjoy all Chicago has to offer?  Massive savings are in store with the Go Chicago card.  Click on the banner below and check out all the discounts!




Art Institute of Chicago
Entrance to the Art Institute of Chicago

More than anywhere else in the USA, I strongly encourage you to visit at least one Chicago museum based on your interests, background, or career plans.  There is something spectacular for everyone here, truly.  Even if you get dragged to your twin brother’s idea of a great museum, I’m confident you’ll still enjoy yourself immensely (and learn a lot, too!).

Here’s just a tiny representation of the museums you can choose from:

Many more exhibits, events and possibilities can be found, again, at the Visit Chicago website.

Now that I’ve gotten museums out of the way… there are plenty of other options for your trip to get totally lit.



Chicago’s skyline is spectacular, and only outdone, arguably, by the world-famous New York skyline.  There are several ways to enjoy the view, “big picture” style as well as up close.

Cycling along Lake Michigan Chicago
Cycling along Lake Michigan
  • Work out your quads as well as your vision via Chicago’s Lakefront Trail.  Not only will you experience lovely skyscraper views along the shore of Lake Michigan, but you will also pass through many beautiful parks, two of which are Jackson Park, with its University of Chicago, and Grant Park, featuring the famous Buckingham Fountain.  Millennium Park and Lincoln Park with its free Zoo are also on your path!  Rent your bike at Bobby’s Bike Hike – 540 N. Lake Shore Drive, Chicago IL 60611.  Ask for maps and helmets, or why not just sign up for a guided bike tour.

    Navy Pier, Chicago
    Fireworks on the Navy Pier
  • Promenade along the Navy Pier for spectacular skyline views and tons of cool things to do. This is where you’ll find the Children’s Museum, Imax theatre, classic carnival-style rides, plenty of restaurant options and the climate-controlled Centennial (Ferris) Wheel, which offers pristine views of the lake and skyline.  Stick around for the gorgeous sunset, and fireworks at specified days and times.
  • Want to round out your skyline experience from within the concrete jungle itself? Like, from the tip top of a skyscraper?  Then I recommend 360 Chicago.  Check on local sunset times, and plan to be here late in the day (while the sun is still out) to enjoy daytime, twilight, and night time vistas, each of which is guaranteed to take your breath away.
    • Now that you can’t breathe, take your death defying to new “heights” (no pun intended).  Sign up for the heart-pounding TILT experience!  You stand facing the views and are engineered safely to stand OUT and ABOVE the Magnificent Mile, over 1000 feet below!    See it to believe it at the 360 Chicago website.



It should go without saying that Chicago is a sports lover’s town.  What kind of cool stuff is there to do for youse guys besides attending a Bulls, Bears, Sox, or Cubs game?

Wrigley Field Chicago
Entrance to Wrigley Field
  • Wrigley Field is the historic home of the beloved Chicago Cubs. Yes, this is the same Wrigley who probably made the chewing gum you love so much.  The ball park is over 100 years old; hopefully the gum you’re chewing right now isn’t.  Anyway, a tour of this mighty piece of sports history bestows a nostalgic feel for the sport of baseball as it was enjoyed back then.  Enjoy baseball the way your great grandparents did!  Depending on whether there is a game scheduled that day, there are different spots (dug out, press box, home base, etc.) within the ballpark on display.
  • Going back to the museum thing: Another Windy City museum to relish involves great fun with cool sports memorabilia and tons of interactive activities.  Here’s what to do: Have a delicious meal of American comfort food at Harry Caray’s 7th Inning Stretch.  While dining at the ‘Stretch, ask for free tickets to the adjacent Chicago Sports Museum!   No need to be a sports fanatic to have a rollicking good time here.  Do check the online calendar first to avoid disappointment if the museum’s closed for a private event.
iFLY excitement Chicago
iFLY excitement
  • Defy death once again (you did TILT… right?) at iFLY, one of a few nationwide spots for indoor skydiving!   After a short but comprehensive training session, you’re instructed to lean into a fierce wind that lifts you off your feet just a few feet off the ground.  Like Superman, you’ll soar (in place), floating on a big column of air.  It’s completely safe, they say.  But then, they make you wear a helmet and goggles, so maybe not?

I would warn you that you will find this experience completely off the chain!  Follow up on  your newfound love by making a competition out of it.  Yes!   This thrilling new sport is  known as “bodyflight.”


What else would you recommend teens to do in the Windy City?  Let me know in the comments.

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