My Chicago Bucket List

Why did I go to Chicago? Simple, the travel bug was biting again, I found $100 round-trip tickets (not including extra fees like carry-ons and choosing your own seats), and the girlfriend wanted to go after giving her a list of destinations to choose one from. Traveling is currently my biggest passion while she hadn’t done much herself and I wanted to share one of the things I love with her. I had recently grown tired of big cities, having lived in or visited Tokyo, Taipei, Ho Chi Minh City, New York City, and many more over the past few years, but something about Chicago was magical and stood out as unique in my mind. The food, the people, the public transportation and the free attractions like the Lincoln Park Zoo and the Navy Pier fireworks show made it stand out as one of my favorite adventures yet. Here is my Chicago Bucket List.


Getting Around: We stuck to navigating the clean, safe, and convenient trains and buses. Easily one of the easiest maps to navigate out of all the places I’ve visited.


3-Day Ventra Passes providing unlimited travel on the Chicago “L” as well as buses for $20 a pop.


We did the build your own Chicago CityPasses for just over $80 a pop to see: The Field Museum, The Art Institute of Chicago,


And two visits to 360 Chicago to see the city during the day and at night.




Navy Pier for a fireworks show, a couple Chicago-style hot dogs, and an amazing view of the city lit up at night.



The “lift” trying Chicago deep-dish pizza.


$4 shots ranging from Maker’s Mark to Patron Silver and $3 Hamm’s tallboys for happy hour!


Chicago sky bars


Chicago Riverwalk


The Bean


Wrigley Field


What’s next? Guatemala!

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