Day 1: Chicago to Tokyo

On Saturday, November 22, 2025, I took the CTA Blue Line to O’Hare Airport. I flew ANA via United, departing at 10:30am and arriving in Tokyo at 3pm the following day.

I hate checking a bag when I fly. Luckily, I was able to pack everything for my two-week trip into my Osprey Fairview 40L backpack and my Peak Design 6L sling. I fit twelve shirts into my Biaggi zip cube, undergarments for each day into a small packing cube, plus a rain jacket, scarf, extra pair of shoes, jeans, pajamas, and toiletries into the Osprey bag. My camera, portable charger, wallet, hand sanitizer, and other essentials went into my Peak Design bag.

I sat in Economy Class. Since it was a 13.5-hour flight, the longest I’ve ever taken, I was a little nervous about comfort and briefly considered paying to upgrade my seat. But I had read that ANA’s economy seats are fairly comfortable and roomy, so I decided to stick with Economy. I’m happy to confirm that the seats really were comfortable, and I felt like I had plenty of legroom.

I made sure to wear compression socks, which I think helped a lot. The food was really good, too. One of the sides was Häagen-Dazs vanilla ice cream, which I don’t think I’ve ever had on a plane before! Best of all, I was able to sleep on the flight and barely experienced any jet lag, which I was incredibly grateful for.