Aug 28-29, 2025
We kicked off our Asian adventure bright and early in Chicago, taking the bus... to the El... to the airport. With our carry-ons in tow and the kind of optimism only pre-flight mimosas can buy, we toasted to our engagement (and to surviving what we knew would be a long day of travel) before hopping on a 14-hour flight to Tokyo.
Now, technically, we bought a one-way ticket to Thailand—because apparently, that’s cheaper than flying one-way to Japan?! So we got off in Tokyo and did not board our connecting flight. Rebels? Maybe. Strategic travelers? Absolutely.
Once we made it through customs, we took the airport train into the city, blissfully unaware that we were about to walk into Tokyo rush hour on a Friday night. We wound up at Tokyo Station, one of the busiest stations in Japan, with over 4,000 trains running daily. Chaos doesn’t even begin to capture it.
We needed to take the green Yamanote Line, which sounded easy enough… until it wasn’t. We climbed all the way up to the platform only to realize there were no ticket kiosks in sight. Back down we went. Tried a self-serve kiosk—no luck. So we stood in the world’s longest “help me, I’m confused” line to talk to a teller, who politely informed us that we didn’t owe anything since we’d come from the airport station. Great! Back up we went again.
Then came the true Tokyo experience: the packed train ride. I’ve never seen anything like it. It was human Tetris. People just kept filing in, pushing, and shuffling until we were literally smushed against the walls. I felt like my niece Annie when she presses her face against the mesh side of a bounce house—completely flattened but somehow still smiling.
Two stops later, we escaped… sort of. The turnstiles wouldn’t let us out because the machine insisted we had the wrong fare. We tried two different exits. Denied both times. With no attendants in sight, we did what any self-respecting, jet-lagged travelers would do—we snuck out behind another passenger. SSHHH- don’t tell.
From there, it was a 10-minute walk… to the wrong hotel. Oops! Luckily, our actual hotel was just 10 minutes in the opposite direction. Once we arrived, we blasted the A/C and collapsed for a minute before venturing out in search of dinner.
We found a cozy izakaya down the street where the chef grilled skewers right in front of us—chicken, veggies, the works. Everything was delicious and very cheap—about $3 per skewer—and the beers came in adorable mini glasses so you didn’t have to commit to a full pint. Even the seats had grocery-style baskets underneath for storing your bags. It was simple, packed with locals, and exactly what we needed.
