You get a bottom-up view of the Chicago skyline-with streets, sidewalks and pedestrians all above the cruise boats on the low-lying Chicago River in Chicago. (Bob Downing/Akron Beacon Journal/TNS)

How I learned to relax and vacation like a grown-up

It started out innocently enough. After a long stretch without vacation, I flew to Chicago on a Wednesday, full of energy and purpose. I would see as many friends as I could, take a trip to Michigan and back (no matter that it was over 200 miles from the city), and catch a 6 a.m. flight back to Seattle on Monday morning bright and early, having packed as much as I could into the intervening four days.

What could possibly go wrong?

As it turned out, a lot. But it wasn’t until I missed my 6 a.m. train to Michigan on Friday morning that I started to question my immoderate approach to travel. As I sat alone on a bench in Chicago’s Union Station, fortified by nothing but Dunkin’ Donuts and a few hours of sleep, I realized what a mistake I’d made. Instead of allowing myself to relax, I had made my vacation into a towering to-do list, and I was having trouble crossing off all the items.

I came by it honestly.

In my 20s, I had spent vacations sleeping in until noon at dumpy hostels or on borrowed couches, subsisting off late brunches and coffee, going out every night with friends and cramming as much as possible into my limited time off.

That wasn’t what my life looked like now, but as I looked up blearily at the grand, sweeping ceiling of the train station and listened to the boarding announcements over the P.A. system, I realized that my travel style hadn’t caught up to the reality of my adult life — I was still trying to travel like a 22-year-old.

But I couldn’t do it anymore. And I knew that if I kept it up, I’d go home frazzled, tired and maybe even sick. It was time to adjust my expectations.

When I got to Michigan, the friend I was visiting was more than game for my new and improved approach. Instead of going out, we made dinner together and watched a bad Gwyneth Paltrow rom-com from 1998. We talked for hours and went to bed early. In the morning, we lingered over our coffee, and when we did venture out in the afternoon, it was to pick up cider doughnuts and take a leisurely wagon ride at a cider mill. On the drive home, as we sang along to the hits of the early 2000s on a throwback Spotify playlist over muddy dirt roads, the bright Midwestern sky an almost cartoonish shade of blue, I felt like I’d finally entered vacation mode. Is this how most people feel on vacation? I wondered to myself. What a revelation.

But my reverie was short-lived. I still had a trip back to Chicago the next morning, and a 6 a.m. flight the morning after, which, along with the time change I was still adjusting to, would almost certainly leave me feeling like a sloth needing to be carried across a busy road.

What would a person not trying to travel like a 22-year-old do?

I thought immediately of the most organized traveler I know: my aunt, a frequent-flying librarian, who’s been known to always pack a dopp kit and a clean pair of underwear in her carry-on just in case. She also has a routine of staying at an airport hotel the night before every early-morning flight to make check-in as stress-free as possible.

I followed her lead.

After some TripAdvisor searching, I found a deal on a hotel less than a mile from O’Hare at a hilarious chain clearly targeted toward millennials, complete with a lobby cappuccino machine, jokey door hangers and potted plants. It was clean, modern and in my budget and had early-morning shuttle service to O’Hare — good enough!

After my bus trip back into Chicago, I took a Lyft to the hotel, checked in, showered — a heavenly luxury after several hours on a Megabus — and drank perfectly decent mass-produced espresso while I unpacked and repacked my luggage.

I spent my last few hours in Chicago browsing my favorite feminist bookstore and enjoying a pleasantly heavy dinner of local beer, gooey ham and cheese on pumpernickel and a starchy pile of fries with one of my best friends from grad school.

Back at the hotel, I scheduled a 4:30 shuttle and a 4 a.m. wake-up call, watched an episode of “Madame Secretary” while eating M&M’s and fell asleep in my fluffy hotel bed before 11 p.m., shades drawn and earplugs in.

Getting my beauty rest while trendy 20-somethings were still flocking to the pool could have made me feel old, but instead I felt exactly the way I did when I turned 30 and realized I never had to go to an outdoor music festival ever again: I felt free and enjoyably uncool. And when I woke up clean, well-rested and even mildly cheerful (!) at 4 a.m., I knew I’d made the right call.

I still ended up getting sick, but as much as it pained me to realize I no longer have the constitution of a 22-year-old, I was glad that I’d figured it out when there was still time to enter the exciting world of reasonable, age-appropriate expectations while traveling. Because here’s the truth: You couldn’t pay me to relive the most regrettable moments of my early 20s. But I didn’t regret the cash I’d dropped on a room of my own at the end of an exhausting journey. Next time, it’s where I’ll start.

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