It seems most likely that when we’re done traveling we’ll return to the United States. We could fall in love with a Thai beach community or a Mexican prison, but it seems most likely that when we’re too old to travel full time we’ll crave the comforts of familiarity.

We’ve settled on Chicago as our most likely future home. We lived in St. Louis for longer than we’ve lived anywhere, but I honestly think we’d have had to leave even if we weren’t fleeing the country.

When we moved to Missouri we thought it was the Southest part of the North, and were surprised to find out it was the Northest part of the South. Still, St. Louis existed as an island of blue in a sea of corn, and it was manageable.

Sadly, the wackjobs have made maintaining that cognitive dissonance untenable. It’s now impossible to forget that you’re living in, and supporting, a state that thinks The Handmaid’s Tale is a rom-com. Missouri has passed a raft of laws reversing local efforts, like St. Louis’s increase in the minimum wage; they’ve tried to nullify federal gun laws; and, of course, they’ve passed one of the nation’s most restrictive abortion bans. Because, women. Am I right?

So St. Louis had a sell-by date on it, whether we became hobos or not.

Chicago seemed the obvious choice for a lot of reasons. First, we’d come to St. Louis because the coasts were no longer affordable, and it’s not like that trend has gotten better in the last twenty or so years. The Sun Belt is obviously headed towards Mad Max fanfic, with warring gangs fighting over half empty Dasani bottles. The northern fringe of the South was too Dukes of Hazzard for us, so the True South is clearly off limits. And the Corn Belt is just desolate, in every sense.

That sort of leaves the Rust Belt. There are any number of interesting, affordable Rust Belt cities enjoying revivals: Philadelphia, Pittsburgh, Detroit, Milwaukee… But Chicago has a number of advantages those other places do not.

At the risk of indulging in sentiment, first among those is family. My sister Nef, her daughter, Amber, and Amber’s husband Tom all live in Chicago. These are people who I’d make part of my family of choice if they weren’t already my blood family. Nef is ten years my senior but many years my junior in her sheer, unadulterated, childlike joy in… everything. It is impossible to spend time with Nef without feeling giddy in the face of the otherwise mundane. When I grow up, I want to be like Nef.

Amber is a kind, gracious, thoughtful, ferociously intelligent polymath. She is good at everything in a way that makes people want to be her best friend, instead of loathing her. If I was as proficient in as many things as she is, people would hate me. Come to think of it, I’m pretty good at a bunch of things. People probably do hate me. No one has ever hated Amber.

Tom is one of the most serious people I have ever met, wrapped in an Oogie Boogie burlap sack of chill. He’s a constitutional scholar who advises emerging democracies all over the world on how to best emerge (we could use his help here). He’s able to explain exactly how you’re wrong about something with both surgical precision and empathy, somehow leaving you grateful instead of angry. He’s done it to me repeatedly (I’m often wrong) and I always want to clap my hands and ask him to do it again.

If these people lived in Piscataway, I’d be tempted to join them. Thankfully, they live in Chicago, which makes it easy. Chicago may be the Second City to New York, but at least as of now, it’s dramatically more livable than NYC. It’s more affordable, less gentrified, more accessible. Every place has its problems, but as much as I miss New York, I have not once been tempted to move back. Even if we could afford it, which we can’t.

In fact, Chicago reminds me a lot of New York when we lived there in the 80s. It was possible to live in New York then and take advantage of the city’s manifest benefits without being a Trustafarian. We just had regular, not spectacular jobs, and for all but two years of our NY tenure, only one of us was gainfully employed at a time. Yet we never felt poor, or that we were locked out of enjoying the best of the city. That’s certainly not true today, but it is true of Chicago. Normal people can live here.

As retirees, the attraction, other than family, is the depth of the cultural scene in Chicago. Just because we reach a point where the constant travel is no longer fun doesn’t mean we’ll be ready to be shut-ins. We’ll want to go to galleries, museums, lectures, dance, theater, concerts, openings… Which is where Chicago shines. New York may beat it on this metric, but probably not by as much as it used to. And housing in Chicago is a fraction of the cost of New York. We can get our big city amenities and not have to eat out of dumpsters. Win-win!

That’s how we wound up in Chicago for Dorothy’s hip replacements. The US government frowns on homelessness, so we needed an actual, real address, not a glorified PO Box. We’re using Amber and Tom’s apartment as our legal US residence, and we chose a Medicare Advantage plan, rather than straight Medicare, for the travel benefits. That plan is Chicago-based, so that’s where the surgery has to happen. Which is hardly a hardship. Chicago is a great healthcare town.

Amber and Tom are renovating a derelict synagogue into the Narrow Bridge Arts Center (donations to Amber’s many worthwhile projects here), which will include living space. Not unlike our project on Cherokee Street in St. Louis, except scaled up in a way that makes us look retrospectively sober and cautious. They currently live in a condo in the same building as Nef. When they move into Narrow Bridge, at about the end of 2023, we’re going to buy the condo, retconning our fiction about it being our residence into a fact.

We’ll rent it out until we decide to stop wandering and settle back down. Or that Thai beach will call to us and we’ll sell it. But if we do wind up back in Chicago, we’ll have an affordable home in the same building as Nef, with Amber and Tom close by. As appealing as that Thai beach sounds, even not having seen it yet, that’s a pretty attractive outcome.

In the meantime, Nef, Amber, and Tom are all in California as I write this, enjoying Camp Little Big Bash in Mendocino, which is usually where we are at this time of year. That leaves us free to stay at our future home for our last few weeks in Chicago prior to returning to Mexico for a couple of months before our daughter Ruby’s wedding and Dorothy’s second hip replacement, both in October.

Being able to test drive it before committing has just made it clear that the apartment is an ideal solution. That’s a great way to end our (first) Chicago interlude.