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This afternoon (morning in Japan, evening back in Chicago – so, I've taken the average which puts me somewhere around 2pm) sees me sitting in a highly desirable business class seat – which I take pleasure in announcing I'll be converting into a bed for the remainder of the journey – for the 13 hour ‘hop' from Chicago to Tokyo. How I managed to secure this seat is quite another issue; basically I was running late to start with this morning. To compound the matter, Chicago's transit authority has taken the liberty to partially close the main airport line and replace just that segment with shuttle buses, meaning in my case, a train, then shuttle bus, then train. It's all a bit confusing. Anyway, it made me even later. Then, if I'm being honest, I never did bother to reconfirm the flight which my ticket goes to great lengths to more or less force you to do. Not that I was hugely concerned – who takes a gigantic flight that doesn't arrive until the following afternoon on a Sunday, traditionally a pretty quiet day in the airline world?

The answer? Half of Chicago. The line-up was worrying. I decided a specific plan was required – namely, friendliness and gently reminding the guy that I was on a round the world ticket and had a frequent flier plan with BMI, their partners. At first he looked a bit nervous – before announcing the ‘unfortunate' news with sincere regret;
‘It's actually a very full…a few too many actually…flight today so I think I might have to put you in business class'. Oh no! What a nightmare! Since then I've been enjoying glasses of French wine, pan-fried beef tenderloin, fresh salmon – basically taking complete advantage of this ‘unfortunate' turn of events. To say that the flight I dreaded the most for the whole trip has turned into a real pleasure would be a severe understatement. Anyway, I need to hurry along, I'm about to cross the date line into tomorrow and let's just say there's a ‘toasted pork cutlet' sandwich on its way in the first 10 minutes of tomorrow, so onto Chicago…

How to enjoy Chicago at night - 1. Find empty space 2. Sit down & Look around 3. Enjoy!

How to enjoy Chicago at night - 1. Find empty space 2. Sit down & Look around 3. Enjoy!

Chicago itself is certainly every bit as manageable as I first suspected it might be. Although I was staying in Greektown, it was just a hop across a highway and then a river to be more or less right in the centre of things. However, the only issue as I quickly discovered, was the lack of any sort of air conditioning or ventilation in my hostel. The first night I took to the bed, it was absolutely steaming. The first two days in Chicago then were spent trying to alternate between air conditioned buildings, finding out about the place and trying to survive the unbearable heat in the hostel – the second night particularly, it seemed to be just burning no matter which way you turned in the bed. The possibility of a restful night's sleep was further disrupted in no small part by the strange inhabitants of the room. Firstly, there was a man right above me who never seemed to be seen by anyone, yet left all his personal belongings that one would normally hide, in full view on his bed – passport, laptop, all not a concern for this guy! Then there was a Brazilian man who seemed to have a rather bizarre liking for sitting in the room listening to his mp3 player (just loud enough that everyone else got a taste of the song) without a shirt – in the dark. I definitely was not the only one locking my backpack at night.

Things got desperate as funds ran out and the bread clearly wasn't helping...

Things got desperate as funds ran out and the bread clearly wasn't helping...

Finally, an escape route to a nicer room came along on Wednesday when Anna finally flew into Chicago. Having not seen her since the morning that crazy old woman nearly tried to execute citizen's arrest on me in Frankfurt, I'd be lying if I said it wasn't nice to see her. That evening however, both feeling extremely poor and lacking money having paid for the hostel bill (although some could correctly argue that I more or less recouped this money through my borderline destruction of the room), we elected to just buy bread and a huge piece of watermelon. Now, I still don't know what was up with the bread or whether we just have touchy digestive systems but having each consumed a large amount of the bread we headed out. I felt full. Very, very full. Certainly much more significantly full than I should have done for the amount of food consumed. Then Anna felt the same. We eventually decided that in fact, the bread was probably that type that expands after being eaten – I don't know what it was, all I know is I thought I never wanted to eat bread again.

Fireworks at Navy Pier...

Fireworks at Navy Pier...

The fireworks at Navy Pier were spectacular – certainly, having hung around for nearly 2 hours to see them, they'd have wanted to have been. They certainly didn't disappoint however – the show lasted a good 10 to 15 minutes and set us up nicely for Anna's time in Chi-town! Being in such high spirits, you can imagine my almost tear-jerking sadness to discover that our private room also had no air conditioning and in fact, as it didn't open out onto the street like my previous room, was even hotter than before making sleep more and more difficult. By this stage however, I was becoming slowly more concerned, along with two Dutch guys I met, that in fact the owner of our hostel was involved in the mafia. He continually seemed to always be in the place you'd least expect like standing on the street when you were coming home late or swarming around your table at breakfast and kept telling people during breakfasts to ‘Stay safe' or ‘See you tomorrow guys, hasta manana' or in my particular case; ‘Take care out there guy'. I kind of got this whole mafia vibe – either that or he thought Chicago was some combat zone that nobody understood the dangers of.

We spent a lot of our time in Millennium Park and Grant Park, home to the Buckingham Fountain, which plays this pleasant light and water show on the hour from dusk onwards for about 20 minutes. The only downside was that there was this strange waterfall that basically showed someone's face for a bit and then they'd get sick – and this jet of water would actually emanate from their mouths onto people below. I'm not too sure what that was about but it was a bit gross in spite of the locals seeming to enjoy it. On the same day, we also made it as far as a little beach just past Navy Pier – people seemed to be out in their millions and the size of the beach coupled with the number of people trying to get space gave it this whole Sandycove feel to it, it'd have to be said.

From there on in, the clouds moved in and thunderstorms came down on top of us. Needless to say, I'd left my jeans that I'd washed (in the shower with me one morning, to save money) hanging out the window. Great. We finished up the trip with a last night at Navy Pier and a proper dinner – the first either of us had really had in quite a few days! It was with sadness then that I dropped Anna out to the airport on Saturday – it's strange, not only is it sad going back to a big room by yourself (especially one that's steaming hot), but also that it could be the last actual meet-up I might have with anyone from Ireland until I get back.

Buckingham Fountain performs one of its 'shows'...

Buckingham Fountain performs one of its 'shows'...

Chicago's a cool place – there's no need if you're living anywhere near downtown to really use the transit and if you can get over it being one of the more expensive US cities, there's a lot of varied things to do – beach, the parks, the sights. Unlike New York, it doesn't seem to depend on its fame and seems much happier to see visitors. It doesn't sell its history or its landmarks and then try and rob people to see and get close to them; if you want to go see Chicago's landmarks, they're right there; but if you don't, it's still a good place to just relax. The streets aren't anywhere near as crowded as New York and people are far more eager to help out.

For now however, I'm sitting in my airline-issued dressing gown and slippers (everyone's wearing them even those who are clearly not planning to sleep so I decided I better as well) and getting a hunger on me that could only be cured by the sandwich (more like a full meal) I'm now trying to balance on my knee while writing…
Until next time!

Reformed backpacker & former ultra-cheap traveller, Andy now atones for his past by overspending on premium travel experiences and failing at making the most of the miles & points game. Based in Malaysia, he is a product manager by day, and travel aficionado by evening and weekend.