Blue Line Blues
First job of the day was catching the Red Line from Clark & Division, and this time we were smart enough to change at Jackson Street — much easier for transferring onto the Blue Line.
The Blue Line, being the only one that actually goes to the airport, is absolutely hopeless when it comes to luggage. There’s no space for cases, barely any space for people, and the layout is so awkward you end up constantly shuffling out of the way for others trying to get on or off. To make things even more confusing, the doors open on different sides at different stops, so you’re forever second‑guessing where to stand. Still, we made it in one piece, which felt like an achievement.
O’Hare International
Our flight wasn’t until 3:50 p.m. (9:50 p.m. UK time), but with long‑haul flights you really do need to be there three hours early. And with trains, you never know when someone’s going to jump under one or cause some other drama that throws the whole timetable into chaos.
After wrestling the bags — strapped to the wheelchair — into a tiny lift, we finally reached check‑in at about 11:30 a.m. Getting rid of the big cases always feels like winning half the battle. There wasn’t much to do before security, so we headed straight through. Being Labour Day weekend, most travellers had already gone wherever they were going, so there was no queue at all. The security woman did have a little moan because I’d put something on top of the laptop in the tray instead of giving it its own, but I’m sure she’ll recover.
Once through, the stress kicked in and all I wanted was a beer. Naturally, the bar was as far away as physically possible, but needs must. Then came the challenge of killing three hours — made worse by the fact that O’Hare doesn’t offer free Wi‑Fi in the main waiting areas.
Killing Time Airside
You get thirty minutes of Wi‑Fi if you’re willing to sit through a two‑minute advert first. So the plan was: thirty minutes on the tablet with a beer, then off to McDonald’s for a burger (same price as in the city, surprisingly). After that, another bar, another drink, and another thirty minutes of Wi‑Fi on my phone. If I’d needed more, I’d have had to break out the laptop or use Jane’s tablet and sit through the advert again.
In the end, none of that mattered. After our drink, we realised the departure gate was practically in another time zone — it felt like a three‑mile walk. By the time we got there, they were already boarding first class. The one pleasant surprise was the plane itself: clearly an older aircraft, so it hadn’t been refitted to cram in as many seats as humanly possible. This must be what economy plus used to look like.
Flight Through The Night
These next bits are taken from the blog I wrote while actually on the plane. We only had one pair of headphones between us, so watching anything together wasn’t an option. The seat‑back screens didn’t work on this aircraft either, though you could stream to your own device — but only while flying over land. Not that I cared; I was happier writing anyway.
17:00 Central Daylight Time
We’re now somewhere over Canada, sitting in economy plus by the window. Definitely better being squashed next to someone you actually know. This plane has two seats on each side and three in the middle, so we’ve lucked out compared to what it could have been.
On the flight out, we were in full “cattle class,” which was awful. When the Muppet in front reclined their seat, there wasn’t even enough room to squeeze past the armrest to get out. No wonder they give you free beer — you need it just to cope. This flight is still better than Virgin Atlantic, but only just. At least the return journey is an hour shorter.
18:00
They’ve just brought the food around — if you can call it that. It’s always something involving rice, isn’t it? You’d think it would be impossible to mess up rice, but plane food always finds a way. The smell alone was enough to put you off.
Next time, we’re definitely buying proper sandwiches airside and skipping this stuff entirely. The only edible thing was a tiny cracker with a little pot of cream cheese.
Hopefully they’ll turn the cabin lights off soon so all the annoying people go to sleep and it’ll finally quieten down.
22:00
Now the cabin lights have dimmed and a hush has finally settled over the plane. People have stopped wandering up and down the aisle and rummaging through the overhead bins for that “essential” item they could easily have kept in a pocket. Like most flights back from the US, this one runs overnight, letting the time difference work in your favour — nobody wants to land in London late at night.
Time does strange things when you’re flying through the dark. Maybe it’s just me, but sleep never comes easily up here, so I end up watching whatever films are playing on the tiny screen in front of me. As you drift along at 37,000 feet, it’s hard to wrap your head around the fact that the world below is racing past at nearly 600 miles an hour, carrying you back toward the familiar rhythm of home.
I’ve said it in previous journals, but it’s always around this point in the journey that my thoughts turn to what’s waiting on the other side — the routine, the work, the everyday life you left behind. The holiday is over, but there’s a quiet optimism too: the sense of future plans forming, and the promise of the next adventure somewhere down the line.
Reflections On The Day: The Long Goodbye & The Slow Drift Back to Reality
Departure days always have a strange energy about them. You wake up knowing the adventure is over, but you’re not quite home yet — stuck in that limbo between holiday magic and everyday life. Saturday had exactly that feeling. The bags were packed, the room was stripped back to its bare hotel‑room self, and Chicago — loud, bright, chaotic Chicago — suddenly felt like it was already slipping into memory.
The journey to O’Hare was a reminder that travel days are never glamorous. Wrestling luggage onto the Blue Line, dodging people, doors opening on random sides of the carriage — it all felt like the city giving you one last nudge of its trademark disorder. But there was also a sense of familiarity in it, like you’d finally learned how the place works just in time to leave.
Airports always amplify whatever mood you’re in. The relief of dropping off the big bags, the mild irritation of security staff, the desperate hunt for a bar, the endless walking to a gate that feels like it’s in another postcode — it’s all part of the ritual. And with the Wi‑Fi rationed out in thirty‑minute chunks, time seemed to stretch and fold in on itself, the hours passing both too slowly and too quickly.
Once on the plane, though, everything shifted. The cabin dimmed, the noise settled, and the world outside turned into a soft, dark nothingness. There’s something oddly peaceful about flying overnight — the hum of the engines, the glow of tiny screens, the quiet shuffle of people trying to get comfortable. Even without sleep, there’s a stillness to it. A sense of being suspended between two lives.
Somewhere over south east Canada, with the ground racing past at 600 miles an hour, the reflections started to creep in. They always do.
Thoughts of home, of routine, of work waiting on the other side. But also the good stuff — the memories made, the things seen, the laughs had, the little moments that stitched the whole trip together. The optimism of future travels, even before this one has fully ended.
Thoughts of home, of routine, of work waiting on the other side. But also the good stuff — the memories made, the things seen, the laughs had, the little moments that stitched the whole trip together. The optimism of future travels, even before this one has fully ended.
Saturday wasn’t a day of sightseeing or excitement. It was a day of transition — the gentle unwinding of a brilliant holiday, the slow return to normality, the quiet satisfaction of knowing you’d made the most of your time. And as the plane carried you through the night, Chicago already felt like a story you’d be telling for years.
A fitting end to an unforgettable trip.
