Chicago, IL – Things To Do!

Before living in New York, I actually lived in Chicago for 6 weeks!  I found out a few weeks before my first clinical rotation of medical school that I would be placed there, so I packed my bags, booked an Airbnb (so convenient for short term stays like this one!), and moved to the Windy City!

I stayed in an area called the Ukrainian Village.  It was a very convenient location, just a short walk away from Wicker Park (what’s considered to be the “hipster” area of Chicago, filled with boutique stores, restaurants, coffeeshops, bars, and music venues).  It was also just a short ride away on the L, Chicago’s train system, from the downtown area.

I ended up going downtown quite often!  It’s such a beautiful city – kind of like New York, but cleaner and less smelly haha.  There’s also a lot to do there.  Here’s a few things that I did that I highly recommend checking out if you ever visit Chicago:

Navy Pier – A 3,300-foot-long pier on the Chicago shoreline of Lake Michigan with tons of entertainment, museums, activities, restaurants, and shops! I didn’t get a chance to ride the ferris wheel, but I still had a great time wandering around on the pier and admiring the yachts on the water.  They’re constantly hosting different events there, so be sure to check out their website before heading over!


Skydeck at the Willis Tower – An observation deck on the 103rd floor of the second tallest building in the United States!  The views of Chicago from here are unrivalled; if you dare, you can even step out onto one of the glass boxes that extend out from the Skydeck at 1,353 feet in the air!  Find out more here.

Eat Deep Dish Pizza – The dish Chicago is known for!  There’s no shortage of deep dish in Chicago and I was on a mission to try as many as possible!  I tried a few well known chains – Lou Malnati’s, Gino’s East, Giordano’s – all of them were good, varying slightly with how the toppings were laid out and the thickness of the crust.  My favourite pizza that I had in Chicago, however, was pan pizza from Pequod’s!  I found out about it from speaking to locals (Uber drivers and fellow Uber pool passengers mainly haha) about their favourite pizza place and all I kept hearing was Pequod’s, Pequod’s, Pequod’s! It wasn’t a tourist hub, which was nice, and I really liked the balance and ratio of their toppings with their crust.  There was also a ring of caramelized parmesan cheese on the crust that just made it amazing.

Check out the Museums – From the Art Institute of Chicago to the Shedd Aquarium and the Field Museum, Chicago’s filled with places to go where you can go to get cultured!  If you’re lucky, you may even be able to score free entry! See if you qualify here for the Shedd Aquarium, Art Institute of Chicago, and the Field Museum.

Cindy’s Rooftop Bar – My personal favourite rooftop bar in Chicago!  The drinks there weren’t cheap, but the atmosphere of the place and the view from the balcony made up for it!  From the balcony, you could see the city, as well as Millenial Park and Lake Michigan.

See Chicago’s Skyline from a Water Taxi – If you want, you can pay $21-23 to go for a boat ride tour of Lake Michigan.  A cheaper alternative is to catch a water taxi from Navy Pier to Shedd Aquarium (or vice versa) for $8-10!  You might not get the full tour experience, but you still get a beautiful view of the skyline and waterfront!

Architecture River Cruise – Chicago is composed of so many different architectural styles and this is the best way to see the buildings that make up the city!  There’s a bunch of different companies that offer this cruise and from what I’ve heard, you can’t go wrong with which one you pick.

Catch a Cub’s Game – Take me out to the ballgame!  The Cubs are one of Chicago’s Major League Baseball teams and I happened to be able to catch a game the year that they won the 2016 National League Championship Series and 2016 World Series (which ended a 71-year National League pennant drought and a 108-year World Series championship drought!).  Whether that had happened or not, however, I would’ve still had a great time at the game!

Lincoln Park Zoo – The Lincoln Park Zoo has all the animals you could want to see and the best part is that it’s free!!  They’re open 365 days of the year and host various events throughout the year, such as craft beer festivals, live music, and yoga!  Check out what events are happening here.

Walk the Magnificent Mile – If you like shopping, this is the place for you!  The Magnificent Mile is an upscale section of Chicago’s Michigan Avenue, filled with shops, hotels, and places to dine.

Cloud Gate (the Bean!) at Millennium Park – Did you ever really go to Chicago if you didn’t take a picture with the Bean?  While it is a nice place to hang out, most people visit Millennium Park to check that iconic picture off of their bucket list.  I’m definitely guilty of doing it haha!




This may seem like a lot, but there are SO many things to do in Chicago – this list just skims the surface!  Chicago is one of my favourite cities that I’ve been to and I can’t wait to go back!

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