Second thoughts about the Second City? No way.

Small compared to my last few trips — London, Montreal, Russia — my jaunt to Chicago approaches with almost unnerving rapidity: in two days. It should be an “easy” trip — short domestic flight, no visas or sourball customs agents — though inevitably there will be a measure of that fly-the-friendly-skies folderol we all know and love. (Baggage fees — adorable.)

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What, me worry?

Easy though it may be, this angsty traveler is strictly a glass half-empty kind of fellow, and that applies to my journeys. With excitement I choose a destination. With a kind of giddy glee I chart an itinerary, winnowing down the sites and restaurants and museums and cemeteries I plan to visit. An anticipatory rush animates the research and planning, and I get revved all over again for the unpredictable adventure of unshackled travel.

I hold onto this fuzzy feeling — until I don’t. As the trip’s date nears a sort of existential nausea, a galaxy of apprehensions, sets in. I mildly panic. My mouth becomes a rictus of worry. I wonder if I’ve made a glorious mistake. Chicagowhat was I thinking? I fret about how nice the weather will be, how acceptable my room will be, how easily I’ll be able to get around. Is the city overrated — is there enough to do and see? Aargh.

I inventoried my neurotic travel niggles in a blog post last fall as I was heading to St. Petersburg, Russia. They have not improved. They have not been assuaged.

Why do I worry so? Because this mostly lone traveler has found some destinations — luckily very, very few — to be a little … lacking. Not bad. Never bad. Never uninteresting, and never without a laundry list of things to do and see. But here and there (say, oh, Boston) a place will offer too much dead air, too little to do to occupy one’s time, too little to enthrall. I get up late and stay up late. Entertain me.

I’m being a bit facetious. Just absorbing a city and the neighborhood one stays in is bracing — a concentrated dose of head-twirling newbie-osity.

I think I have Chicago down. Like, down. I’m staying in an Airbnb that happens to be a room in a luxurious downtown boutique hotel, not someone’s crib. It abuts the 360 Chicago skyscraper in the Gold Coast on Lake Michigan, in the same hood as the Museum of Contemporary Art and the (oh, yes) International Museum of Surgical Science.

It’s too early in the season for river boat tours, but not too early for a slew of city walking tours. I’m booked on the Famous Tastes of Chicago Food Tour, a three-hour amble of hot dogs, pizza, Italian sandwiches, chocolate and architectural superstars. I’m holding a hot ticket for the critically salivated-over play “The Wolves,” a finalist for the Pulitzer last year. My dinner reservations are otherworldly. The lush, star-studded Graceland Cemetery beckons. A brace of fabled bars, The Hideout and The Empty Bottle, are sure bets.

Just reading all that serves as verbal Xanax. Calmer, even optimistic, I can take care of business, like packing, which takes me approximately 12 minutes. Then what? Travel is what. It’s a drill I know well. Get to the airport, check in, blunder through security, get to the gate, wait, board, soar. The rest is the adventure, the big show, which should be joy-inducing, eye-opening, head-expanding. It is where worry and angst go to die.

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