Editors Note: The original intention was to post a description of my Summer 2009 roadtrip closer to the time that it occurred, but now 2010 is approaching and since I’m not even half-way through I need to get on this!

When we drove through Gary, IN fighting through the traffic and then seeing Chicago’s skyline in the distance, my breath was nearly taken away. A gorgeous cluster of brilliant lights, penetrating the night sky. I could see why Batman was filmed here. We drove through the multi-lane highways and towards the place of our couchsurfing host for the next few days: Patrick. Emerging off the Interstate and onto the road, I was shocked at the number of cars parked along the streets. There was no space for additional cars! We eventually got lucky and found a spot though. Walking up to Patrick’s place we realized we were starving. It was late, just before 10pm and a Chinese place let us order from them as they were closing. Such nice people!

We went up to Patrick’s apartment, introduced ourselves and ate the Chinese food. Patrick was a great guy that really loved Couchsurfing. He had just hosted a girl for several weeks! That’s dedication. We were exhausted and couldn’t join him on his night out with friends from the Pitchfork Music Festival so we re-arranged the living space and hit the mattresses with exhaustion.

I vaguely remember what happened, but Jane and Erby definitely did. Patrick’s roommates walked in and called friends complaining that more couchsurfers were there and that they were tired of having people sleeping on their floor. The next morning, we awoke, went out to get some Cuban breakfast and discussed this turn of events. How unfortunate, Patrick was such a great guy but it was uncomfortable to stay where we weren’t wanted. After getting some trip planning done at a coffee shop, we returned and found the roommates there. When we explained that we’d only be there for a few nights, they were relieved… they thought we would be there for another month! Apparently the last guest had exhausted her welcome.

We set out and about the city, to see the Miraculous Mile. The Threadless store, The Hancock Center, the deep dish pizza, the walking around lost, the concert at Millenium park. It was all fantastic. Free classical music at millenium park was the best moment of the trip so far, and maybe even one of the highlights of the entire trip, now that I’m looking back. Amazing acoustics with the backdrop of a city. Brilliant. The rail line that would take us back to our lodging was out so we waited for a bus that was absolutely packed and we found another way home. It took us about two hours to get back and we just ended up taking a taxi anyways.

The next day we went downtown to catch the art museum before it closed, but it closed early because it was a Sunday. So we went to the International Museum of Surgical Sciences for a super gross-out experience. We closed out the stay in the Capitol of the Midwest by partaking in a movie with Patrick. We saw Food Inc., the film adaptation of “The Omnivore’s Dilemma”. He enjoyed it and it gave us a great talking point for burgers and beers at The Counter afterward. We had some belgian waffles with a fun street vendor and said our goodbyes and passed on our many thanks.

The next morning we set out around 7:30am for Sioux Falls, SD to beat the worst of th Monday morning rush hour traffic but to also ensure that we left around the same time Patrick did for his grocery clerk job. We had a long day ahead of large roadside objects and nothing was going to keep us from seizing that day.

Chicago was a fantastic experience, and a frustrating one. The largest US city I’ve ever visited while driving… it was full of cars! Even taking the bus a few kilometers took an hour or more on these grizzled and gridlocked streets. A fun place to visit but because of the big business mindest, the prevalence of chain stores and the high cost of living I knew that this was one place I’d never want to even accidentally end up living in.