The big 3-0: Day two – exploring Chicago

Last time out on the blog I kicked off my HUGE 30 day trip to the USA in the summer of 2018. I wanted to do a detailed day-by-day round up of my trip. Those of you that read day one will know it wasn’t too packed with excitement.

My first day was really about traveling to the US, a good chunk of it was spent in the air. I tried to make the best of the evening, a firework display certainly helped, so it wasn’t an entirely non-eventful day. However let’s be honest, this is where the trip really got going. On to day two!

I woke up on Sunday morning having had little more than 12 hours in Chicago and a good chunk of that was sleeping. So I was up early and raring to get out and explore! My time in Chicago was sadly very limited, before day two was over with I’d be departing.

“Why so soon?” I hear you ask. Honestly, I was a little disappointed to only have one night in Chicago but the city is one of the most expensive I’ve ever been to. When I began to look at accommodation options I was in disbelief at how much it was going to cost me.

It didn’t help that I was there during Chicago’s summer and over a weekend of course but accommodation prices were ludicrous. I couldn’t justify paying for two nights so decided I’d be better off spending one of those nights sleeping on a Greyhound bus to my next location, Minneapolis.

Anyway, getting back to day 2..

I was eager to see as much as I could before leaving so I made an early start to my day. I left my hostel dorm as quietly as possible, leaving my suitcase with reception, and made for the streets of Chicago! The circumstances were far from ideal. I would LOVE to have spent longer in Chicago but I wasn’t about to sit and sulk about it. I knew it was a short amount of time to explore but left myself with three objectives for the day!

See the famous ‘Bean’, go to the Skydeck (Willis Tower) and lastly eat some Chicago pizza. All three seemed easily achievable, anything on top of that I considered a bonus.

I decided to kick off my day where I’d finished things off the previous evening. I’d had a little chance to familiarise myself with where things where on day one and decided I’d head back in the direction of Navy Pier to begin my day. I’d seen it all lit up after dark and I was interested to see how it compared during the day.

Additionally, because it had been so dark, I hadn’t bothered venturing to the nearby beach area. I wanted to take a look around Ohio Street beach and see how this beach area co-existed in a downtown area full of massive skyscrapers.

Chicago is nicknamed “the Windy City” so it was perhaps unsurprising to find there were already some early-risers making the most of a wind-free day, enjoying the early sunshine and making the most of the opportunity to use the beach.

It was a beautiful day for it but rather than don my swimwear I swiftly moved on and wandered back towards Navy Pier. It’s much more spectacular by night if I’m being honest. It felt a little lifeless during the day, although it was still a little early on a Sunday morning for much to be open.

I hadn’t planned to stick around for long anyway, I only wanted a quick glimpse because I had places to be! I was hoping to see the Bean before it got too crowded so that was my first real stop of the day.

For those of you not familiar with Chicago or the Bean, it’s probably the most famous landmark in the city. Officially its name is “Cloud Gate” but its nickname required little imagination. See for yourselves!

After a number of photos I left behind the growing crowds and decided I needed to find myself some breakfast. Given it was to be my first breakfast of this trip, it seemed only fitting that I find somewhere with pancakes on the menu.

I was winging it though, I wasn’t sure where I was going and figured eventually I’d pass a diner or cafe or somewhere that would appease my breakfast choice. My breakfast hunt took me past several cool pieces of architecture and bits of street art.

This little “Alice in Wonderland” looking garden was probably one of the highlights. I’m not sure what its actual purpose is but it made me think of Alice in Wonderland anyway. I also kept passing these colourful little lighthouses which I thought were really cool!

After a little while I stumbled upon somewhere that seemed suitable for what was now a late breakfast / early lunch. I guess that’s the downside to spontaneously winging your food options, opposed to doing prior research. Breakfast was good though and I felt content heading on to my next stop: the Skydeck!

Before coming to that we’ll take a little trip down memory lane and reminisce of my trip to Sydney in 2013.

“Wait, what?”

Stick with me, I promise there’s a point! You see, Sydney was one of my very early trips as an adult and my first traveling solo. To combat some of the nerves I planned everything. I knew Sydney meticulously. I was giving the locals directions..

Alright, I might be exaggerating that last point but seriously, I’d done so much prior planning that I knew central Sydney inside out before I’d even stepped foot in the city. I had everything down on paper to offer me further assurance I knew where I was going and what I was doing. I had confirmation emails double printed, those confirmations packed seperately and blah, blah, blah..

In the years since I’ve become much more of a “go-with-the-flow” traveler because I’m more sure of myself. I’m more spontaneous but more flexible too. “I’ll find breakfast somewhere in Chicago.. it’ll be fine..”

I’d say there was a great deal of winging it for the bulk of my 30 day trip but one thing I’d made sure to book in advance of this trip was a ticket to the Skydeck. It was a popular attraction and I thought by planning ahead, perhaps naively on my part, that this would save me time when it came to actually visiting the Skydeck.

That wasn’t the case! Imagine my horror at discovering there was a TWO HOUR wait to get to the top, even with a ticket purchased in advance! I’ve no doubt that this is a fantastic attraction, I’ve heard good things about it but my advice to you would be to not book in advance.

What’s the point really? You still find yourself queuing with passengers who’ve arrived on the day. Sadly I wasn’t in Chicago for long and I decided I wasn’t going to spend a chunk of that queuing for this so I cut my losses. I was out of pocket but figured I might aswell give my ticket away rather than let it go to waste, or try to anyway.

You wouldn’t think it should be that difficult to give a free ticket away but it took me having to ask a good half a dozen people
“Do you want a free ticket?..”
“Oh.. no.. thank you.. there’s clearly a catch you’ve neglected to mention”

There’s no catch, just take the bloody ticket off my hands! Eventually one of the sceptics agreed and allowed me to get away and get on with the rest of my day. Sadly it meant that I’d failed in one of my objectives for the day and I was a bit irritated about it. I now needed a plan B and the best way to decide that was over a “cuppa”. There was a nearby coffee shop and they say tea cures everything, right?

I wasn’t going to let the “Skydeck experience” ruin the rest of my time in Chicago. Feeling a bit more refreshed I headed back out on foot and made my way down to the river which has a nice promenade-like area alongside it. There are a handful of restaurants and bars and things close by but more than anything, it’s just a really nice part of the city with a great view. It was a beautiful day for a little people and boat-watching. I could easily have spent hours in the area to be honest.

After a little time wandering I seeked out somewhere for lunch, one of my guilty pleasures when traveling infact. Long time readers will know I’m fond of the Hard Rock Cafe’s and I was keen to tick off my 18th different HRC location. There’s a charm to them that leads me to visiting them when possible and Chicago’s was no different – a good atmosphere, good service and good food.

I still had a good few hours left to explore Chicago before catching my bus but didn’t really have much planned. I’d seen the Bean, failed with the Skydeck and the last thing on my list was Chicago pizza which I figured would be easy enough for dinner.

So I just wandered aimlessly for a while after lunch, keeping my eyes peeled for anything interesting. I continued passing many more of those lighthouses I’d seen earlier (there was 51 in total – look!), found some other cool murals and then stumbled upon a little art gallery tucked away. It was small but helped kill a little time.

Chicago’s a nice city, it’s one I found easy to walk around and continually find little things that catch your eye. After exploring for a while I turned my attention towards my departure. I had to collect my case, find somewhere for dinner and then find somewhere that I could hang out prior to catching my bus.

It didn’t make sense to collect my case first and then have to take it to dinner. However I figured it made sense to find a restaurant near to my hostel, I knew on the corner was this pizza place and it had a real buzz about it when I passed it the evening before.

The place was called ‘Pizzeria Uno’, it was equally busy tonight and inside was beautifully decorated. Along the wall were signs paying homage to some of Chicago’s other landmarks, Pizzeria Uno being one itself! I didn’t realise this at the time but a Google search suggests this restaurant is where deep dish pizza originated.

Perhaps that’s why it proved to be so popular but it seems I picked a good place to have my first taste of Chicago’s famous delicacy. I’m not a massive foodie but I was still excited to see what all the fuss was about. I have to say it was pretty good!

I don’t know if this is the best place in Chicago to try deep dish pizza but it was good enough for me to recommend a visit, particularly so given its history.

That said, whilst enjoyable I’m less convinced about deep dish being the best pizza around! It still has a long way to compete with pizza in Italy or even New York! I’m glad I tried it but it’s not pizza I’d be fussed at eating anywhere beyond Chicago.

Following on from dinner I went and picked up my suitcase and then made a slow walk towards the Greyhound bus station. I still had a bit of time to kill so I figured I’d find myself a bar somewhere on route and have a couple of beers. I made sure it was only a couple though. I was still a little bit of a walk from the station so didn’t stay too long. I’m someone that hates being late for anything so I’d rather sit in a station for a little longer rather than test my luck against the clock.

It was probably just as well too. I got right in to the vicinity of the station with a bridge being the only thing standing in my way from reaching my destination. Halfway along the bridge I discovered the pedestrianised bit had been cordoned off. My only options were to either play chicken in the road or turn back and find another way over the river.

To my right I could see another bridge which I thought would be my quickest route to go around and get back on track. To my more immediate right was a tunnel which I was pinning my hopes on leading me towards this bridge.

Sadly this tunnel seemingly leads nowhere. After a few minutes of walking I was pondering where the exit to this tunnel was. I hadn’t anticipated it being too big and I figured any second now I’d see the outside world again. Cars kept whizzing past me which, presumably, were coming from somewhere.

After what was probably ten or fifteen minutes I then fell in to that awkward trap of not knowing what to do. On the one hand I was asking myself if I admitted defeat and just turned back. It might be another 10-15 minutes in the direction I’d originally come from but at the very least I’d make it out of this horrible place alive!

On the other hand, if I’ve walked this far am I committed to this now? There HAS to be an end to this place, surely? With each passing minute ticking by I risked missing my bus. I was meters away from this bloody place and this supposed small detour had completely screwed me over.

I persisted forward BUT to this day I still have no idea where this tunnel ends. Eventually I stumbled upon a small pedestrianised area to the side and escaped asap! Why there’s a pedestrianised exit here? I have no idea!

This isn’t a place anyone should ever visit on foot but I was grateful nonetheless! Now with a sufficient phone signal again I discovered I was miles away from where I needed to be and there was no way I’d reach the bus station in time on foot.

I flagged down a taxi in a race against the clock and hoped we wouldn’t get bogged down by traffic. Fortunately there seemed to be little on the roads and I arrived with a little time to spare but it was a needless and exhausting ordeal.

Given I blog about trips so far in the past, every so often I ponder the ridiculousness of certain experiences and doubt my memory. I find myself questioning if it could possibly have happened just as I remembered it. This is one of those occasions where I looked to the internet for some sort of validation that Chicago’s underground maze is a reality.

It appears that Chicago’s underground city and network of tunnels is a lesser known ‘attraction’ of the city. ‘Choose Chicago’ make it sound absolutely wonderful here with underground bars, quirky streets, places to shop and lovely street art to look at.

I don’t know where that underground paradise was but it at least adds some substance to my experience of spending an eternity under the streets of Chicago. Fortunately I was now free! Getting on to my bus I felt a little more relaxed, found myself a seat and crossed my fingers that I’d get some sufficient sleep for the over-night trip to Minneapolis.

Stay tuned for day 3!

Jason