Trek America, The Grand Trek: Exploring Chicago

Trek America, The Grand Trek: Exploring Chicago

“A journey of a thousand miles must begin with a single step.” – Lao Tzu


Emerging from our tents after a good night’s sleep, we were back in the van and en route to Chicago!

Being a slightly long drive, we had two stops before Chicago to break up the journey a little. Our first point of call; an Amish town named ‘Shipshewana’. I didn’t really know what to expect from an Amish town – it’s not something us Brits really encounter on a daily basis, and something I didn’t really know much about.

As soon as you enter the town’s vicinity, you are transported to what feels like another time completely. Yes, cars are still passing through on the roads, but the road’s tarmac is dominated by Amish buggies, led by horses, and for solo travellers; bicycles. Women are dressed typically in long dresses in muted colours, matched with a bonnet, whilst the traditional Amish man is dressed in plain black trousers, a shirt, and either a straw, or black hat.

Being immersed in a completely foreign culture in the middle of the States, was a pretty surreal experience for all of us and something I think, everyone was totally unprepared for. We shuffled into an Amish museum to learn a little more about the culture and the way the community lived their lives (with a lot of dressing up in Amish clothes involved), before starting the second leg of the journey to a town called ‘Gary’ in Indiana.



Gary was grim.

As in, they actually film horror movies there because the place is now so desolate. A huge chunk of the local shops had shut down, (minus a few liquor stores), abandoned buildings with smashed windows lined the streets, and there was hardly anyone around. Overall, it was a very creepy place to be but really interesting. I’ve never really been anywhere like that before, and it was interesting to see another side of America that isn’t typically seen by tourists. It almost made the whole experience seem a little more realistic, as prior to this everything had been super-sized and fantastical.

We stopped in a neighbourhood-street dotted with small bungalows, again, with nobody to be seen – minus an old man at the bottom of the street, sat at a stall selling Michael Jackson t-shirts and posters… we were at Michael Jackson’s first home (spoiler alert: it’s tiny).

Having visited Chicago 5 years prior with my family, I was eager to get back inside the beautiful city, and especially excited for the others to see why Chicago held such a fond place in my heart.

We stayed in HI Chicago hostel which is hands down the best (and first), hostel I’ve ever stayed in. It’s hard to say what made it such an amazing place to stay, as the fact that we had actual beds was a bonus within itself.

One thing that I appreciated so much, and something that in a normal situation, you wouldn’t even consider, was walking around in socks! Before Chicago, it was flip flops on to go to the shower block, and around camp, so for me, walking around our spacious dorm-room in my socks was a huge novelty!

chic HI.jpg

In terms of the hostel ammenities, as well as the enormous rooms with en-suites, plug sockets and a lamp next to every bed, the hostel also provided table tennis, pool tables, free wifi, free popcorn, free breakfast, free ping pong, free movie showings, and wait for it…

free alcohol.

Granted, they only do the popcorn and alcohol thing at the weekends but what an amazing place!

We ordered some typical Chicago deep dish pizza before heading out for our first taste of Chicago, in the form of Bobby’s Bike Hike.

Trek America had organised the tour in advance for us and we were on the City Lights at Night Bike Tour. Bobby’s Bike Hike offer a variety of tours from walking trips, to a ‘Southside Gangster Bike tour’ to their ‘Bikes, Bites and Brews’ tour, plus, their website indicates the level of the cycle ride from ‘ridiculously easy’ to ‘moderate/intermediate’, allowing you to pick exactly how strenuous you would like your tour to be!

Our bike tour was already included in the price of the trip, but as American culture dictates, it’s recommended that you throw in around $10 each for a tip at the end of the tour. We started cycling just before sunset, which made the experience even more beautiful and allowed us to experience Chicago in two completely different ways.

The beginning of the tour saw us hugging the shores of Lake Michigan, passing by a volleyball tournament, and eventually, stopping to capture an impressive view of the city as the sun was just setting. One thing I loved in particular about the tour was the incredibly fun approach the tour company has to showing you their city, that they are so obviously infatuated with.


A quirky aspect to the tour involved ‘whoop whoop’-ing, in unison whenever our guide initiated it. However, as the tour is infamous within Chicago, we found so many passers-by either joining in with us, or encouraging us to start ‘whoop’-ing for them! Countless people waved us on, cheering us and yelling “Bobby’s Bike Hike!”, in a sort of stranger-to-stranger understanding of how good the tour was!

The next 2 1/2 hours were spent weaving through the streets of downtown Chicago, stopping every so often to take in the sights and learn a little more about the magnificent city.


Full of deep-dish pizza and Chicago culture, we headed back to the hostel to take full advantage of our comfy beds for the night!

The HI Chicago, offers a surprisingly large breakfast spread, which we fully utilised
before heading out to explore.

Our first stop of the day was the Willis Tower, the tallest building in the Western Hemisphere, which boasts incredible views of the city (unfortunately for us, we visited on a pretty rainy day). The Skydeck is the most popular aspect of the tower, especially for tourists, based on the 103rd floor and at 1,353 feet in the air, the Willis Tower showcases ‘the ledge’; a glass box jutting out 4.3 feet from the tower itself.

team glass
If you’re afraid of heights then I’m going to be straightforward and let you know that this one will not be for you. Plenty of people make it up to the skydeck and choose not to step out onto the ledge though, so if you can face your fears and make it up to the 103rd floor, you can wander around, taking in 360 degrees of Chicago’s best features.

Jumping on to a bus, we shuttled across to the Adler Planetarium, which wasn’t originally on our to-do list but amazingly, Bobby’s Bike Hike gave us free tickets so it seemed stupid not to go!

I’ve never been to a planetarium before, so we paid a little extra and went to one of the shows, which if you do go to a planetarium, you HAVE to do it! We went to see ‘Cosmic Wonder’, although I’m not sure it matters too much which show you pick, as they all seem completely mind-blowing (talking about space makes me feel like such a tiny human and I freak out a little – but in a good way), and you are completely transported.

Entering the room before the show, you were instantly greeted by the gorgeous pinky-glow of the dome, and as you made your way to your seats there was a murmur of excitement (in very muffled tones), from the people plonked in their almost-horizontal and super comfy seats.

The Cosmic Wonder show was a combination of a gentleman with THE most soothing voice ever, talking us through the constellations that illuminated on the roof of the dome, and teaching us all about solar systems, galaxies and other space-things that make you feel weirdly small. The show itself was really interesting and visually, really impressive! Although, a guy sat behind me fell asleep completely and started snoring really loudly and really erratically , so I spent the last part of the show feeling like I was at a school assembly, trying to stifle hysterical laughter.

Coming out of the planetarium we spotted Navy Pier in the distance and decided it would be a great idea to walk there along the coast of Lake Michigan. It wasn’t a great idea. It was one of those moments where you think that because you can see something, it must be close.

It took us an hour of power walking in the rain to get to Navy Pier, but we made it!

The Pier itself is lined with shops, restaurants, bars and even some rides, with people sailing past on boats and kayaks.
chicago day

Sadly, we had spent so much time in the journey to the Pier, we scoffed down some food and raced back to the hostel in time for the baseball game later that evening!

Immersing ourselves in the full tourist experience, we shoved our Maid of the Mist ponchos on, grabbed ourselves a supersized pint of Bud, and plonked ourselves down ready to watch the Chicago White Sox play!

I’m not a huge sports fan myself, but the American’s know how to do sporting events! Whether it’s the free bobble-head of a player you receive when you walk into the stadium (random but a nice gesture I guess?), the nachos served in an edible nacho-hat, or the dance-cam and kiss-cams that feature when there is a natural break in the game, they know how to get the crowd going.

So if going to a sporting event in the USA wasn’t something on your radar as sports don’t necessarily interest you, note that the atmosphere itself was much more interesting to me than the game itself and you can get involved in the game in loads of different ways; our group even made it onto the big screen during the dance-cam break!

We spent the rest of the evening in a bar called ‘Kasey’s’, chatting to fellow travellers, or if you’re me -sat on the floor stroking all the dogs that were in the bar before heading back to our last night in a bed for a while!

Thanks for reading!

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