Two Days in the Windy City: My Take on Chicago

Rather than explore new cities with appreciation, I have a tendency to be comparative and envious, always looking at a place’s perks through gritty, Philly-colored glasses.

In reality, I know that Philadelphia has a tremendous amount going for it. No where have I found a more walkable city, with flourishing new neighborhoods like Passayunk Square, Northern Liberties and Fishtown and hidden gems like the Magic Garden and the new Sister Cities Park.

That said, I am a person who walks into a home not quite as nice as my own and become depressed that I don’t live there. I am someone who should stop using Pinterest as I covet thy neighbor’s armoire.

But back to Chicago, a city which I am happy to say I found perfectly lovely but am not inconsolable at the thought of not moving there (as I have been with both Montreal and London). Although I will say that, as usual, the public transit system makes Philadelphia’s look like a toilet on wheels.

I only spent about 48 hours in the Windy City and absorbed as much walking, shopping, and eating as one could reasonably do. I got to experience the touristy but not at all overrated Deep Dish Pizza and Second City Theater (old stomping ground of legends like Tina Fey and John Belushi, not to mention my favorite author and Spit That Out contributor Abby Sher.)

I ate the most insanely delicious, elaborate, and expensive dinner of my life a Moto, a renowned Mecca of molecular gastronomy. I fortuitously walked smack into an extravagant gay pride festival, as I am wont to do in all my travels. Here I ate locally crafted ice cream for lunch and did 20 pound ball slams to work it off (and show off for no one in particular).

We walked down part of the “Magnificent Mile” which was really no more than an amplified Walnut Street, laden with high end retail chains and peppered with Chipotles and Starbucks. Unimpressed we headed to Wicker Park, the “hipster area” akin to Park Slope in Brooklyn or maybe even Northern Liberties. But I will happily spend a day there, as they have several shops carrying hard to find eco fashion and homeware and even a new outpost of eco-baby store Sprout San Francisco. I just wish someone would have warned me about the 10% sales tax before I picked up an Amour Vert top on sale.

One of the coolest parts of the trip was running along the Lakefront. But while this seemed like a rare experience, I realize it wasn’t tremendously different from running along Penns Landing or Kelly Drive. It’s just that once I’ve managed to run from my home to these places, I’ve just about enough steam left to turn around and go home.

And that sort of sums up how I felt about my short trip. I’ve seen it all, likes what I saw, and am ready to return to my regular stomping ground. Which is how a vacation should feel.


Very excited that OHare airport has filtered water fountains and lots of recycling bins. Doesn’t take much to thrill me.
This was the “menu” at Moto. Sampling of the 12 courses.
And here’s the final course: an edible version of the menu.
For one course they set fire to some pine needles for “ambiance.”
One of my favorite courses – foraging for mushrooms and meat
A super cute eco-friendly shop in Wicker Park. Please come to Philly!
This shop had a great selection of eco fashion mixed in.

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