Table for One in Chicago

As the wife of a commercial pilot, I am well-acquainted with doing things solo. I have attended parties, weddings, holiday gatherings, “couples” nights, and everything else possible as a party of one. However, until recently I had never traveled solo.

I met a friend of mine in Portland, OR a year ago for a girl’s weekend. She arrive the day before me and just hung out in Portland. She explored, ate in restaurants, talked to people and shopped solo and had a great time. I felt a little jealous! I never before thought of traveling like this. In the back of my mind I always wanted to do a trip alone, but figured I wouldn’t because between my hubby and friends, someone was always down for a trip.

Such a beautiful, fun and friendly city

Then we moved to the Midwest and I needed to fend for myself in a strange place (with shitty weather) and after not seeing hubby for more than two days out of 30, by April I decided we needed some time together. I decided we should visit Chicago. Hubby is based there so I could easily take a short flight to the Windy City and meet up with him for a romantic weekend.

I flew in a on a Saturday and he had to work until Sunday. So off I went, from O’Hare to my downtown hotel, on public transportation, meeting new people along the way. I loved my hotel and the neighborhood. I needed to go do stuff on my own; but what?

After a cocktail and salad in my hotel restaurant (which were amazing), I silently made fun of myself for not leaving my hotel. Why was it so hard to walk out the door and explore? I read a great review about the best Mexican hot chocolate in the city (America) so I decided to walk a few miles on a Saturday night while everyone around me was walking to a late dinner with friends or waiting to get into a club for a bachelorette party (seriously, I walked past like five parties doing this!).

That’s when it got weird—but not for me. I surprisingly didn’t care that the server/host/floor manager at this adorable little casual dining establishment was visibly confused by my “nope, just a party of one. Yes, I want to eat here” (followed by me saying internally ‘because eating outside on the curb like a party-of-oner should, just wouldn’t do, pal’). He sat me at a counter space with my amazing glass of Mexican hot chocolate while I waited for my order of three churros. Yes, three. Don’t judge me.

Best meal ever---EVER!

When my churros arrived, I immediately drifted off into a lovely deep-fried, chocolate- and pistachio-coated heaven.  I no longer noticed the way-too-drunk tables, who really were entertaining to watch. And the two girls next to me who kept staring at me, I reasoned they were just jealous of my fabulous food and shoe choice and smiled.

The next morning I walked around again to a new part of the neighborhood. I found that no stores, not even in Chicago, stock gloves during late-April despite the fact it was freezing. Then I found out that the Chicago Magnolia Bakery is good, but New York’s is better, and that enjoying a city—or any new place—solo is fun! You can see and do what you want, relax and talk to new people, and it’s a great experience. But then I saw my hubby walk up to the hotel and I remembered that I also really, REALLY miss him when he is working and I still love seeing him in uniform, and despite the fact I now have another opinion to take into account for shopping, eating and destinations, I have a lot of fun with my pilot.