Chicago Fun: Top 5 Unique Activities You Can’t Miss

So, planning a trip to the Windy City? You’re in for a treat! Chicago, actually, it’s not just about deep-dish pizza and wind – I mean, it definitely is about those things too, don’t get me wrong! Very, though, beyond that, there are a ton of cool and different experiences waiting for you. You might even plan it with a friend! This article is designed to walk you through my top five picks for fun things to do in Chicago that are a little bit off the beaten path. Alright, lets get started.

1. Architectural Boat Tour: See Chicago From the River

Instead of just walking around and looking up (which, yeah, do that too, it’s impressive), imagine this: you’re cruising down the Chicago River. Seems, almost, like you’re gliding through a concrete canyon where these enormous buildings rise up on either side! In fact, very talented tour guides tell you the story behind each building; almost sharing the secrets of how these sky-high artworks came to exist. These aren’t just buildings, actually, that they’re showing off! Arguably, it’s a trip through different architectural movements and historical moments. Is that the perfect photo opp? Book it quick because, I promise, it gives you a great viewpoint.

Think about this: I did the architecture boat tour, right? Well, it was during sunset, and seriously, the way the light was hitting the Wrigley Building…well that’s why the boat tour made my list! Also the best is being able to casually gaze upwards instead of breaking your neck while walking!

2. Explore the Art Institute of Chicago: More Than Just ‘Ferris Bueller’

Of course, the Art Institute is super well known; yet, that awesome scene from “Ferris Bueller’s Day Off” is usually the first thing that jumps to mind, isn’t it? But, more or less, seriously, I urge you to go beyond that. I mean, they actually have world-class collections! From amazing Impressionist paintings to historical artifacts, truly you could spend days lost in that place. But there’s just so many items to view. Plan your visit strategically so that is how you make the most out of it!

Okay, here’s what I suggest: go straight for the Thorne Miniature Rooms. Alright, they are super detailed miniature versions of actual historic rooms. Each is designed and it will blow your mind how much precision and care has gone into each one!

3. Catch a Show at Second City: Laugh ‘Til You Cry

So, you want a good laugh? Well, Second City’s what you need! Seriously, they’re known for putting out a huge array of comedic geniuses like Tina Fey, Stephen Colbert, and Steve Carell. I mean, right? That they’ve passed through Second City says enough. Often, their shows are fresh, witty, and will likely have you doubled over. As a matter of fact, its also very engaging! Grab tickets early; usually these shows do sell out quick because it is super great fun!

Now, my piece of advice: don’t sit too close to the stage unless you want to be part of the act because that could happen at any show.

4. Walk the 606: An Elevated Park Experience

Instead of just regular old ground-level parks, how about an elevated one? The 606 is a repurposed, formerly unused, railway line that’s now this cool path for walking, biking, and seeing public art! I mean seriously, in some respects, its an awesome way to discover several neighborhoods you might not go into. More or less, it gets better when the sun is out. By the way, just see it for yourself when visiting. Plan your route for your specific activity.

In fact, that, if you like street art? Be sure to watch for all kinds of cool murals under the bridge along the path; because they’re quite good.

5. Dive Into Chicago’s Food Scene: Beyond Deep Dish

So, lets say that Chicago is famous for deep-dish pizza and hot dogs, that it really doesn’t even stop there! Seriously, this city’s food scene is just brimming with incredible diversity. Right? That goes far, far beyond those iconic dishes, actually. Why not get your feet wet? Seemingly, Chicago has nearly anything your heart desires! The question you need to ask yourself is this: why wait for lunch, in fact treat yourself now! You might even try new restaurants and hidden food spots too.

Instead, go grab a Chicago-style hot dog – I swear it’s good because they are nothing like you’ve tasted, they are topped with so much stuff!