Chicago Illinois United States

Things To Do In Chicago

Welcome to the Windy City, aka Chicago! This place has been on my bucket list for so long and it is 100% worth it so here are a few of my favorite things to do in Chicago It’s the perfect blend of a big city and the suburbs. It was just like a movie- were greeted with the perfect sunny day, runners in the park, lots of greenery, and beautiful buildings reflecting the blue sky. It’s like a miniature New York City without the chaos, hobos & expensive cost of living. Sounds pretty good to me! Let’s dive in on the top things to do here!


When Is The Best Time to Visit Chicago?

For started, just know that Chicago has pretty extreme weather. Especially in the wintertime, it can get pretty unbearable. Overall, the best time to go is May-August, and March if you want to celebrate St.Patrick’s Day there which tends to be very crowded! 

How To Get There?

Similar to NYC, there are a few airports you can fly into. Chicago has two major airports, Chicago O’Hare International Airport and Midway International Airport (which is what we flew into). We flew with Southwest for the first time and LOVED it! 10/10 recommend! 

Where To Stay?

I cannot recommend Getaway Hostel enough! It’s the perfect spot at the most affordable price in the city. They have complementary breakfast every morning, social events if you’re traveling solo & in a great location for nearby restaurants & stores!

Images By: TheBrooklyniteAbroad.com

Top Things To Do in Chicago

Architecture Tour: Did you know that Chicago is known for its architecture? It’s the birthplace of American skyscrapers and this boat tour takes you through its incredible history. Everyone and their mothers were telling me to do an Architecture tour and well that’s what we did.

The tour is about 1.5 hours and it’s rain or shine so bring a poncho, umbrella, and a good camera to capture the magic of Chicago’s skyscrapers. With that said, I recommend Wendella Tours since they’re the OGs! Check them out here! https://www.wendellaboats.com/

Images By: TheBrooklyniteAbroad.com

Chicago Museum: Did you know that Chicago is known as, “the crossroads of America?” From the Industrial Revolution and trading to inventions and entrepreneurship, Chicago helped connect Europe, the East Coast the Midwest, and beyond!  honestly had no expectations going into my visit. I didn’t do a lot of prior research and going to this museum was exactly what I needed to get a surface-level understanding of Chicago’s history! 

Navy Pier Ferris Wheel: If you like Ferris wheels, you can get a pretty iconic view of the Chicagoan skyline!

Green Mill: Did you know that Al Capone used to come to this speakeasy? He had his booth! It’s an iconic landmark in Chicago that’s history goes deep. Don’t worry about visiting on the weekdays- it’s just as lively. I went on a Tuesday and they brought in a blues band who was phenomenal. What an experience!  

Images By: TheBrooklyniteAbroad.com

Places to Eat In Chicago

Dash of Salt & Pepper: For a hardy breakfast, go here! It’s in a great location near a local part to chill after and get some sun! 

Lou Malnatis: You can’t go to Chicago and not try deep-dish pizza. At first, I did not know what to expect and I was surprised at how it tasted. The crust is a little harder but more raw in a weird way. I still prefer NYC pizza, but for deep-dish pizza, this is the place to go!


There You Have It 

Visiting Chicago for a little 3 day weekend was everything and more! I mean hey, you might even want to consider living there – I thought of that (not forever), maybe just another trip visit down the line! Let me know which places you’re most excited about and enjoy your trip!

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