How-to guide: On visiting Chicago like you're from Chicago:

One’s visit to the city starts before the trip even begins; in the wardrobe. Whatever you do, heed no advice from your aunt. To visit any city, you must ditch the tennis shoes and the backpack. Impractical shoes are a must. 

Do you have a map? Good. Put it away. Out of sight, out of mind. Taking the train into the city is a good way to test your wits and city know-how. The night before prepare a loose plan of navigation that you’ll forget the moment you step out of the station. Next plan of action? Start walking. 

Stop to devour cupcakes whenever possible. (especially when Feta & Strawberry with Pine Nut Brittle is available) More Cupcakes on Delaware Avenue makes this step particularly enjoyable. Now keep walking!

Don’t forget to take in the sights. There’s a lot to see in this city other than your reflection in the bean. 

Keep walking. You’ll see things that you never thought you’d see, like 212 blocks of industrial chicago and an urban farm (which will seem oddly appealing even though you’ve lived in farmland your whole life). You might start wondering why you didn’t take public transportation, but rememeber! You’re young! You’re healthy! And it’s a beautiful day to boot! 

…The following portion of our trip was left undocumented due to heat exhaustion and visions of smoothies. Please imagine pictures of a million glasses of water accompanying a tasty panini from Letizia’s Bakery, some great places like Greenheart Fair Trade store and Renegade Handmade, and an hour or two of conversation and recuperation at a coffee shop (which wasn’t really that cool, so we’ll leave the name out)…

After all of this marvelous adventuring, you’re probably hoping to find a way back to your train. You’re probably hoping too that this doesn’t involve much walking. It’s probably okay to just grab the next bus that comes to your stop, even though you didn’t really spend much time trying to understand the bus system.

It’ll take you where you want to go, don’t worry. 

And maybe the beach wasn’t on your list and it’s further from where you meant to go, but the water will feel really nice after a long day of walking.

Since you’re now terrified to venture into the territory of public transportation, you’re just going to need to backtrack the route that your bus took you. You might think you feel the skin wearing off of the bottom of your feet as you start to walk again, but rememeber! You’re young! You’re healthy! And it’s a beautiful day to boot!  

.. but go ahead, pull out the map.