a weekend in Chicago during Covid

I haven’t flown on a non-Delta aircraft in over a decade, but when a travel newsletter I get said American had round-trip flights to Chicago for $49 a few months ago, I bought 5 for the weekend of Sept. 11. Why that date and that city?

In 1997, I graduated from Alabama and moved to Atlanta to begin working at IBM. I didn’t have any friends in Atlanta, so when a guy named Jesse showed up at my hotel room during an out of town training class and introduced himself as my roommate, I was glad to have a new work friend who’d also grown up in the South and graduated fairly recently from Ga Tech. He later told me the emails I sent my friends from college in the voice of Civil War Generals describing our time in the “real world” as if we were navigating battles were “weird,” but we bonded anyway, and we stayed in touch even after I left to go to law school, and he left to get his MBA.

Shortly after I met my bride in 2005, Jesse sent me a wedding invitation in Chicago, and I took her with me. We loved the city and all we got to see and do there that weekend. In fact, my bride has a framed photo next to her side of the bed of the 2 of us atop the Hancock Tower in the Signature Lounge from that trip. Ten years later, I had a legal conference in town, and we took our children for a 4-day weekend, and we loved the city once again (and got to spend time with Jesse’s girl, Liz). So, when this deal came for my bride’s birthday, I got 5 tickets, so that we could spend her birthday in the city where we may very well have decided we loved each other.

American does not appear to prioritize flying safely during Covid quite as well as Delta has. On our 3 flights with Delta since mid-March, we were spaced apart, boarded from back to front, and were handed bags of water, hand sanitizer, and snacks as we entered the fuselage. Middle seats were empty. On American, we seemed to board like we’d have boarded in 2019, and the plane was packed. I was glad it was a short flight. Having learned many flights ago that I can’t wear glasses + a mask and expect to read on a plane, we downloaded a David Sedaris book on Audible and listened together on paired headphones (via our new Airfly device!), so I could keep my foggy glasses in their case.

After our hotel room was cancelled by Covid, my OG friend from blogging, Jim, gave us his apartment for the weekend, so after meeting him briefly for a tour, we headed to the Art Institute for our best Ferris /Sloane/Cameron impression.

That night, the children got Portillo’s hot dogs delivered to Jim’s apartment, and the Mrs. and I went to our reserved time at The Aviary. I learned about it a few years ago via a podcast with the co-owner/creator, and we went to its New York version last December, where I named it one of my top 5 bars in the world. My bride bought me its beautiful cocktail book for my birthday in June; now it was time to experience it.

We opted for the “5-course cocktail tasting menu with paired food,” and it was absolutely amazing: perfect combination of theater, “snacktivity,” and epicurean delight rolled into a couple hours.

We then walked over to Sushi Dokku (a suggestion by Jim’s son, Kevin) for a bit, until the city’s mandated restaurants’ closure time of 11, a lesson we learned by taking Uber to other places Jesse or Kevin had suggested and realizing they were all closed.

The next morning, we went to the Field Museum to see Sue and other animals / exhibits before meeting Jim, his son Kevin, and Kevin’s girlfriend for deep dish pizza at Lou Malnati’s on the patio before returning to the Field Museum and having an early dinner at Monteverde (we could only get a reservation at 3pm), one of the places Phil Rosenthal went during Season 3 of Somebody Feed Phil. It was absolutely delicious, and just as he did for us in New Orleans, Tokyo, Florence, and Venice, Phil steered us well for culinary exploration in yet another city. Afterward, we walked Millennium Park (but had to see “the bean” from a distance, as it was marked off for Covid) and tried to go atop the Chicago Athletic Association (like Phil did and Jesse suggested), but it too was closed for Covid.

That night, we enjoyed the sunset from the rooftop deck of Jim’s apartment, and then my bride and I went to The Office, the speakeasy tucked beneath The Aviary for some “dusty bottle” cocktails that were just as we remembered enjoying nearly a year ago in NYC.

Sunday morning, we had a 10am brunch reservation at Roister, the casual restaurant (but still with a Michelin Star) in the Alinea group, where I had the best chicken and waffles I have ever had (and believe me, I have sampled MANY chicken and waffle plates).

We met Jim again for goodbyes and to grab our suitcases. We had the Uber stop at Bric-a-Brac Records to explore nostalgic collectibles and buy some vinyl before catching our crowded flight home.

This trip included the best dining and drinks of any trip we’ve ever taken, yet it was one of the least expensive vacations we’ve ever had, as lodging and airfare were free or nearly free. I spent more time in a mask than I’ve spent in over 40 Halloweens combined, as Chicago does not mess around when it comes to demanding PPE indoors (including rideshare cars, airplanes, etc.), which grew more annoying with each day. We were happy to be back out of the Atlanta airport, in my personal vehicle, or inside our house Sunday afternoon, where we could be mask-free for a few hours for a change. We watched “The Fugitive” Sunday night so we could see more of the city in its “normal” state (as normal as watching Tommy Lee Jones chase Harrison Ford throughout its streets can be).

I love going to Chicago and that we got to give my bride a special birthday weekend that she loved, but I love it more when there’s no pandemic going on.


  1. Deborah Moebes

    Masks aside, I felt deeply treasured and spoiled by you on this trip. Lots of reasons to love Chicago, and to go back again when we can hug the locals freely, like God intended. <3 You give me the good birthday love!

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