My kinda town, Chicago is

I don’t do much work travel, especially now that I freelance, but this week I had an assignment that required a (very) short jaunt to Chicago. I was welcomed with foggy, wet, chilly weather, but I didn’t mind — Chicago is a city very near to my heart, in any conditions.

I was doing the math with Dan the other night: we’ve been to Chicago together 3-4 times and all told I’ve made at least a dozen visits. We kicked around the idea of moving here once, years ago… I don’t think it would have been a fit for us but man do I love to visit any chance I get.

I was lucky to be able to visit a Kimpton Hotel, a boutiquey favorite chain of mine. The Kimpton Hotel Allegro is Art Deco to the hilt.

The client I was visiting took care of us, including lunch at Gibson’s Italia and a very memorable happy hour in one of these igloo-bubble-things on Chicago’s newly-renovated riverwalk. The bubbles are probably intended for cool, brighter days — they were a little swampy on a night like we had — and we crammed the space with a few too many people, but it was fun regardless. There are no strangers in a steamy bubble.

I extended my stay by a day to catch up with friends. Jessica, a friend of roughly 20 years, chose Bar Siena. Pictured here: fill-your-own doughnuts (Nutella, salt caramel, vanilla bean and raspberry). Not pictured here: table-slappingly-good sweet corn ravioli and a Mezcal cocktail I wish I were drinking this very minute.

Here is the beautiful Jessica. (Fun fact: she side-hustles as a makeup/beauty YouTuber.) We don’t see one another very often but we keep in touch online. When we get together, it feels natural to pick up where we left off.

In the morning before catching my train, I was also able to see the hilarious and charming Henry. He works around the corner from the Allegro and chose Eastman Egg as a meetup spot based on a Weird Al reference in a review of their egg sandwiches. Sooo. Friends for life. We didn’t even choose the egg sandwiches.

(By the way, I swear Henry has a soul… I think the filter I used turned him a bit demonic. Sorry, H. I’m sure I could fix it but oh noooo I’m already hitting the button)

It has been 3 years (to the day, oddly) since my last visit to Chicago. I didn’t even eat pizza or go to the theatre or visit Improv Olympic this time around. Does that even count as a trip to Chicago?


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