Given that I’m from Chicago, you could probably guess that it’s one of my very favorite places in the world. I get goosebumps every time I fly in and see the lake and that skyline and museums and ball fields. But after 30 years of winters and wind chills, it didn’t take long to become spoiled by Austin’s gloriously mild winter weather. Since you can’t take the winter out of Chicago (And who would want to? The Magnificent Mile during the holidays is spectacular.) I just have to get my fill of Chicago life whenever I’m able to visit.
My first night in town included dinner with Toni at the new Eataly just off Michigan Avenue. There was pizza, pasta, and gossip, and even though the Chicago Eataly isn’t nearly as big as the NYC Eataly, it’s just as overwhelming.
There are walls of beautiful produce and imported specialties.
I had two days of conferences to attend, but was able to sneak away to my favorite part of town…
to my favorite restaurant…
for a solo lunch (#romantic). If you’ve never been to Chicago Pizza and Oven Grinders call a cab, book a flight, or start walking right now.
Mediterranean bread is one of life’s greatest pleasures. They number the shakers of special spices at each table so nobody walks off with it, as you’re wont to do (and I may have done on one very sneaky/brave occasion).
The pizza pot pie is the most perfect version of deep dish pizza that has ever existed. It comes out in a little dish that the waiter flips over in one quick swoop to reveal stringy mozzarella, steamed mushrooms, and a salty/buttery crust that you’ll have dirty dreams about.
Of course, no trip to Chicago would be complete without Garrett Popcorn. Go early and often (they close at 8 pm) and always order a size bigger than you think you want. I left with $50 worth of Chicago-style.
After I was conferenced out, I caught the South Shore to Indiana, where my dad picked me up for a day at home. I used to take the train into the city pretty often with friends in high school and it’s exactly the same as I remember it.

Between the old Polish ladies at the ticket counter, the conductors punching tickets, the mix of old and young riders, and the pleather seats, I don’t think anything’s changed in 50 years. I love it.
I forgot what an interesting view of the city you’re able to glimpse by train. A lot of the neighborhoods are decrepit and sad but the buildings are beautiful and the neighborhoods are busy. I wish more than anything that the south side would see a resurgence.
The station in Indiana is near one of our old houses — we lived here when I was in kindergarten. The front right windows were my bedroom, which was decorated in a pink Swiss dot that matched the blooms on the magnolia tree perfectly. That tree was hit by lightening more than 25 years ago and there’s a big gash down one of the main branches that I used to climb, so I was surprised to see it on the cusp of spring.
My trips home are always a little bittersweet because Floyd is getting older, but he’s still full of the same piss and vinegar as always — just with more naps.
I was only home for one full day, but pizza with family is always on the agenda. As are selfies with cousins.
I left early Saturday morning, my luggage bulging after a shopping trip with my mom, but there’s always room for my very favorite candy from my dad.
After a whirlwind few days, it only took a quick two hour nap and I was back in Austin, planning a return trip to Chicago.



Yes Yes Yes to Garrett Popcorn! And to Chicago Pizza, although I was always drunk when I went there, so my endorsement doesn’t mean as much as yours.
A drunk endorsement is the best kind of endorsement.
Beautiful travel log. I had no idea Nutella was available in such a large container. Floyd is adorable.
Thank you. I never know if they’re only interesting to me and my mom. 😛