My Top 5 Things to do in Chicago

Sweet home Chicago. It’s home of the blues and heart-stopping pizza. It’s also home to its share of tourist traps. Thankfully I am here to set you straight. So skip the Miracle Mile and Navy Pier in favour of my top 5 things to do in Chicago.

Wander Grant Park

On top of my list of things to do in Chicago is wandering the massive Grant Park. I was lucky to score a great deal on a parkside hotel which left me centrally located to explore its 319 acres. Highlights for me include the Museum Campus and Buckingham Fountain – famously known for the opening scene of Married with Children.


Grant Park is also home to a smattering of festivals with Lollapalooza being one the most famous. Coniceditally it is still on my bucket list. Time for a return to Chicago?

Visit Wrigley Field

If you’re lucky enough to be in Chicago during baseball season, don’t miss going to a Cubs game. Why? Certainly not because of the home team’s century-long+ championship drought. No, for the stadium itself. Baseball’s 2nd oldest stadium has so much character it’s tough not to love, baseball fan or not. If you’re in town during the off-season you can still visit this historic site. Guided tours are available year-round which gives you a VIP peek behind the scenes of this historic Park.

via Flickr CC @jc3663
via Flickr CC @jc3663

Things to do in Chicago

Things to do in Chicago

Eat Deep Dish Pizza

Sure, Chicago deep pizza is essentially an artery-clogging bomb of cheese and meat, but when in Rome? There’re those that passionately argues that Chicago deep dish is not pizza, but you won’t find those heaters in Chi-Town. Depending on who you ask, chain giant Giordano’s or Lou Malnati’s serves up the best pie. I tried both… and nearly died in the process.

Worth it.

Things to do in Chicago

Climb Willis Tower

And by climb I mean take the elevator to its 103rd-floor Skydeck. I know I said this list of top 5 things to do in Chicago was skipping the tourist sites but I also said it is my top 5 things to do in Chicago. Those that have been following along know I love a good view. Whether it’s the world’s tallest tower in Dubai or Lions Head in Cape Town, I must conquer it. Willis Tower is America’s 2nd tallest tower and 14th tallest in the world. Naturally, the Skydeck offers incredible views. Don’t miss its glass balcony and watching the clouds roll in below you!

Things to do in Chicago

Things to do in Chicago

Take in the Public Art

Rounding out this list of my top 5 things to do in Chicago is taking in its awesome public art displays. Scattered throughout the city you will find impressive (and often massive) pieces that inspire and delight visitors and locals alike. There is a high concentration in the downtown area called The Loop. Taking an art walk through The Loop is a must-do Chicago activity. Cloud Gate is a giant silver bean that is the most popular and most photographed of all Chicago’s outdoor art pieces. It certainly caught my attention, but can you blame me?


Things to do in Chicago

Things to do in Chicago

Things to do in Chicago

Other pieces I found fascinating are the Crown Fountain, a digital display of changing faces, and the 109 iron legs and torsos that makeup Agora.

What say you?
Thoughts on my top 5 Things to do in Chicago?
Let’s hear it!

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