Our Route 66 grand adventure kicked off with a rather frustrating delay at Gatwick, just enough to make our connecting flight in Reykjavik Airport a delightfully stressful dash. What was supposed to be a simple hop across the pond quickly became a thrilling race against time, because who doesn’t love that kind of excitement when traveling? We finally touched down in Reykjavik Airport, clinging to the optimistic hope that our onward flight to Chicago will be also delayed – and it appeared we were in luck!
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At some point we we were wondering if we’d get an to stay overnight stay in Reykjavik Airport and catch a connecting flight in the morning. And as for our poor luggage making the connection in the roughly 30 minutes available? Well, that seemed about as likely as finding a quiet corner to read a book. We’ve learned our lesson, next time only direct flight if available.
We were still hoping we will manage to make it to Chicago in time for our eagerly anticipated Route 66 journey starting on the 19th! Still couple days to get there. Somehow.
Crowds in Reykjavik Airport
We arrived to Reykjavik with some delay and we still had time to board the airplane to Chicago. “Hurrah!” – I thought. However, the joy was short lived. That flight was delayed too and despite the Airport being so conveniently compact you could practically high-five someone at the furthest gate from anywhere, the overcrowding was nothing short of spectacular. Finding a place to sit was apparently a Game of Thrones, and the queues in the shop, even for a basic human necessity like water, were so efficiently long that attempting it without having 2-3 hours on our hands was simply out of the question. Ah, modern travel at its finest!


By the way there were completely no trees around Reykjavik Airport. Just a black volcanic rock. It looked somewhat charming. I could see some grass outside, but very little.
Finally we were boarding!
Long Immigration in Chicago
The flight from Iceland to Chicago was long, and somewhere over the Atlantic, I hit that point. You know the one. Where the movies lose their luster, the book feels heavy, and even the airplane magazine’s safety instructions start to seem like riveting literature. On top of that your back starting to ache and every bone in your body feels like it has been removed and put back. An hour before landing I was staring at the map of the flight path on my screen and waiting for this damn flight to land. And then, as we started our descent and the pilot announced we were approaching Chicago Airport. I continued staring at the screen on the final approach with a intensity that was probably both ridiculous and slightly alarming to anyone who happened to glance my way as if I had a stroke or something.

We finally touched down at Chicago International Airport, only to be greeted by an immigration queue that seemed to stretch into another time zone. Seriously, I’ve never seen anything like it! It was a winding river of weary travellers, snaking back and forth across the vast hall, a true testament to the joys of international arrivals. Thankfully, my returning ESTA meant I breezed through in a mere 15-20 minutes – so quick they didn’t even bother asking questions, which was almost disappointing after the travel saga; I was almost ready with a witty anecdote. However, my poor travel companions, navigating the system with a first-time ESTA, got to enjoy a leisurely three-hour standing ovation in the queue. Three hours! That’s enough time to watch a feature film, read a novella, or contemplate the meaning of life while shuffling forward two feet at a time. One really does wonder if packing a foldable chair and a portable TV should become standard carry-on for such occasions, or perhaps a small tent for an overnight stay within the queue itself.
Meanwhile, outside the hallowed halls of border control, mountains of luggage sat patiently waiting for their owners who were presumably still somewhere in the immigration labyrinth, if they were lucky enough to make it through. Suitcases of all shapes and sizes piled up, a silent monument to the bottleneck just beyond the doors. You could almost hear them sighing, wondering if they’d ever be reunited with their people. Eventually, though, through sheer perseverance (and likely some very tired immigration officers), our entire group successfully cleared border control, blinking in the bright light of the arrivals hall, ready to finally start our adventure (and hopefully reunite with our bags soon!). It just goes to show that sometimes the biggest hurdles in travel aren’t the flights themselves, but the grand reception committee waiting for you upon arrival.

We collected our rental car and put two additional drivers just in case. Interestingly the plate of the car was from Florida!

First Motel in Chicago
Finally we were on our way to our pre-booked motel, cruising through Chicago’s famously wide streets. And when I say wide, I mean wide – sometimes five lanes across! It was quite the contrast to the confined spaces of the airport, offering a sprawling welcome to the city that felt both impressive and perhaps a little overwhelming after our travel ordeal.

The shiny neon sign of “Stay at Heart O’ Chicago” motel has welcomed us on our way in. We’ve got an apartment on the 1st floor with two queen beds. It was clean and tidy, so it all seemed good.



Tomorrow we would explore Chicago!