Okay, so I needed to make the trip from SG to Chicago. Quite a haul, that one. Wasn’t my first long flight, but still, you gotta prepare.

Getting Started: The Plan
First thing was figuring out the flight. Spent some time checking options online. You know how it is, comparing prices, layover times. Didn’t want to spend two days just travelling. Found a route, I think it was through maybe Japan or somewhere? Can’t exactly remember the stopover city now. Booked it. Felt good to have that locked in.
Then it was the usual stuff. Make sure passport is good, check if any visa things were needed. Luckily, that part was straightforward for me this time. Packed my bags, probably too much like always. You think you’ll need all sorts of things, right?
Departure Day: Off We Go
Got myself to Changi Airport. It’s always a smooth process there, gotta admit. Checked in my main suitcase. Always have that tiny worry – will I see it again on the other side? Went through passport control, then security. The usual routine: belt off, laptop out, liquids in the little bag. Found my gate, waited around. Grabbed a coffee.
Up In The Air: The Long Haul
Finally boarded the first plane. Found my seat, settled in for the long sit. It’s just hours and hours, isn’t it? Watched a movie, tried to get some sleep, which never really works well for me on planes. Airplane food came and went. Standard stuff.
Landed for the layover. It was good to stand up and walk around properly. The airport wherever it was felt huge. Had a few hours, so just wandered a bit, stretched my legs. Then it was time for the next leg. Boarded the second plane. More hours staring at the flight map screen, more trying to sleep.

Touchdown: Chicago O’Hare
Eventually, we landed in Chicago. O’Hare airport. Big place. Felt good to be on solid ground, even if my legs felt a bit like jelly. Then came the lines.
- Immigration: Waited my turn. The officer asked the usual questions – why I was visiting, how long I’d stay. Got my passport stamped. Always a relief.
- Baggage Claim: Headed down to the carousels. Found the right one and waited. And waited. Then, success! My suitcase appeared. Grabbed it quickly.
- Customs: Another line, but usually moves quicker. Handed over the form, quick question, and then I was through.
Out and About: Final Steps
Walked out of the secure area into the arrivals hall. First job, figure out how to get to the city. Decided to try the train, the CTA Blue Line they call it, goes right from the airport. Bought a Ventra card, topped it up, and found the platform. It was pretty easy, actually.
The train ride took a while, but it was interesting seeing the suburbs turn into the city. Got off at my stop, walked the last few blocks. Finally reached the place I was staying. Dumped my bags, felt exhausted but also kinda accomplished. A long journey, door to door. First thing on my mind? A hot shower and finding some real food.