The Great American Road Trip: Cleveland & Chicago

The Great American Road Trip: Cleveland & Chicago


// June 25th CT → Cleveland, OH //

We said our goodbyes in Connecticut and started our return journey back to San Francisco, now along the top of the country. First we made our way through New York and then past hundreds of crazy reckless motorcyclists on sports bikes racing along the New Jersey highways. The racing stopped as soon as we crossed into Pennsylvania and the surrounds turned into peaceful rolling hills and farmland. We rolled into Cleveland around 4pm, checked into the hostel, and were immediately underwhelmed. Instead of spending time in our dingy room, we drove around the edge of Lake Erie and found ourselves in an up and coming re-purposed industrial neighborhood with luxury apartments, breweries, and millennial-geared bars under the bridges. Once over the bridge into the downtown area, we saw skyscrapers, fountains and lots of cute restaurants and beautiful architecture. I don’t know why Cleveland gets such a bad reputation when it’s actually a nice place to be. It started getting dark, so we walked around our neighborhood, past an abundance of breweries, and back to the hostel for canned veggies and chili for dinner.

// June 26th Cleveland → Chicago, IL //

I was so proud of us for getting up early enough to go for a run. We jogged around the surrounding neighborhood, down to the water, along graffiti murals, past the market and back to the hostel before our meeting with the hostel owner. I held my tongue about the stained pillowcases, but didn’t linger too long since the interview was just as dull as the hostel’s atmosphere. The drive to Chicago was easy, only five hours through the northern part of Indiana. The traffic only started to build as the Chicago skyline came into view. I was immediately struck by how massive this city was. Sleek modern skyscrapers dominated the view, many of them a dark onyx color that gave you a feeling that some seriously important business went down there. Lake Michigan snaked in between the buildings, creating gorgeous canal walks for all the professionals on their afternoon strolls.

The hostel, Fieldhouse Jones, was in the north side neighborhood. We checked in, dropped the car off at Midas for an oil change, and walked back to the hostel, taking the scenic route through the neighborhood. This hostel was such a drastic comparison to the dingy one in Cleveland. Instead of questionable stains and crusty pots and pans, this one was professionally designed to look like gym and had luxurious marble countertops and stainless steel appliances. Never before had I seen double bed bunks with memory foam mattresses and floor to ceiling locker space. It was pure luxury.

Our instant rice and canned chili seemed out of place in the face of such luxury, but we made use of the sparkling kitchen and made our way to Millennium Park for the evening. The cloud bridge was everything I expected, except for the name. I naively thought this mirror sculpture was called the Bean, but the artist named it the Cloud Bridge as the mirror gives the viewer the feeling that they’re looking into another dimension. After taking our obligatory selfie in the mirror, we hopped over to the Walgreens across the street for some beers to bring over to the Jay Pritzker Pavilion for a live jazz performance. Instead of the scheduled performance, they swapped in some bizarre Swedish techno trance band. Maybe the beer helped, but we stayed for the whole show, partially just to see what strange thing the band would do next.

// June 27th – Chicago //

For the second day in a row, we woke up early enough to go for a run, which was a great way to explore the city, block by block and be amongst the crowds making their way to the office. We made it to the edge of the lake, through the skyscrapers and along the waterfront sidewalk, passing a number of other runners and bikers. At the beach and along the Milton Lee Olive park, we turned around and headed back through the Gold Coast and Old Town neighborhoods to the hostel for a breakfast feast of bagels, cream cheese, fruits, cereals, and real coffee. The kitchen area was filled with a mix of a few backpackers like us, families, and even a woman from Kenya who was here for her citizenship interview. We pigged out and walked over to Freehand Hotel for an interview with their general manager. The Freehand brand is really interesting to us because they’re owned by a massive hotel company, but offer luxury shared accommodation, merging elements from both hotels and hostels. It seems like this is a design that will be popping up more and more as big hotels realize that they can appeal to more millennials through this layout. As far as shared accommodation goes, this one was the swankiest, with beautiful dark wood, and well designed rooms with unique furniture.

After hearing the manager’s perspective and getting a tour of the property, we walked around the upscale Magnificent Mile shopping district and along the sun soaked canals. Back at Fieldhouse Jones, we had another meeting with the owners of the property and then went back out to walk along the canals in the opposite direction, towards Navy Pier. The pier reminded me of Fisherman’s Wharf in San Francisco with the big chain establishments, like Bubba Gump Shrimp and TGI Friday’s and tourists weaving in and out on Segways and bicycles.

One of the girls I lived with in San Francisco on Haight Street had moved to Chicago with her fiance, so Byron and I met Hannah and Jason at their favorite Chicago Deep Dish pizza place, Lou Malnati’s. We reminisced about our time in San Francisco but acknowledged that we were both happy to be saving in rent after leaving! Stuffed full of gooey cheese and pepperoni, we said our goodbyes and took the local commuter ferry along the river at a fraction of the price that the tourist boats charged for the same experience. We passed underneath countless bridges with the skyscrapers towering above us and hopped off in Chinatown.

The road to the main drag weaved through apartment buildings and through an indoor/outdoor mall, similar to the ones I’d seen in Hong Kong or Southeast Asia. As everyone knows, you can’t walk through Chinatown without buying bubble tea, so we indulged in a hazelnut flavored tea and strolled underneath the Asian-styled gate, past jewelry stores, electronic shops, and noodle restaurants. A long line of non-Asians stemmed out from an ice cream restaurant and as we got closer we discovered this wasn’t just any ice cream shop, but it was “rolled” ice cream, which had recently become the newest food trend. We fed into the craze and took our place in the line, snapchatting the experience as the girl behind the counter poured liquid ice cream onto a stone, set to a below-freezing temperature. As the liquid made contact with the stone, the consistency thickened until she scraped off the ice cream in rolls and placed it in a cup with tongs. It was thicker and creamier than normal ice cream, but as with most novelty foods, it’s more of a try-it-once kind of deal. Tired and full of sweets, we Ubered back to the hostel for bed.

// June 28th Chicago → Sioux Falls, SD //

Third morning run in a row! We were killing it! We went along the water’s edge again, but this time a different route to the north. Again, our run was rewarded with a hearty hostel breakfast and conversation with some other backpackers. The Canadian and German that sat across from us were roadtripping all the way from Whistler to Montreal, through the northern part of the USA.

After some frustration with the car not being ready at Midas (even though I gave them two days to do a freaking oil change), we were back on the road. Our route took us through Wisconsin, so naturally, we stopped at a local shop off the highway for some cheese. Because, what else do you do in Wisconsin, right? I drove through the farmland as Byron fed me pepperjack and “bread cheese” on slices of white bread. We rolled onwards through Minnesota for hours and hours of grassy plains interrupted only by farm houses and giant wind turbines. It sounds weird, but the rows of giant white blades spinning around looked majestic and kind of beautiful in the late afternoon sun.

After hours of little to no signs of human civilization, we were relieved to see the signs for Sioux Falls, South Dakota. The KOA campsite had a peacefulness to it, with a light breeze flowing through the leaves on the trees while we set up our tent. The sun dipped lower and other campers pulled in and started up their grills for dinnertime. We walked around the circle to “window shop” for which camper we thought we’d like to live in most, eyeing the silver chrome Airstream in particular. We probably looked like camping amateurs as we pulled open tin lids from our green bean and soup cans for dinner. If we were making this a lifestyle, we’d definitely invest in some serious Coleman level gear, but for one month, we figured we would rough it. We played cards until it was too dark to see the numbers and prepared for the cold to set in. We realized that ditching our blanket in CT was a terrible horrible decision that we would pay for dearly as we shivered and pulled on every possible layer of clothing we packed, just to get warm enough to let our bodies fall asleep.

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