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Chicago, Take Two

Chicago has never really been nice to Jamie and I, despite our two attempts to be its friend. We tried Chicago in 2003 or 2004. We don't remember the date because it was a trip worth forgetting. I was in law school, we were broke, but we needed to get out of our lives for awhile. I think it was possible that we were also renovating our house at that time, too. Obviously, we should have stayed home, but I wanted to go somewhere. Chicago sounded easy. Chicago is cool. Also, surprisingly, it wasn't that expensive. Of course, I later learned that it wasn't expensive because I booked a room in a bed and breakfast outside of the City. The bed and breakfast I chose was in Oak Park. Our room was in a big mansion and it had a fireplace, Jacuzzi tub, champagne welcome. Perfect... except for the fact that it was a half-hour, one-way train ride into the City. Those of you who have traveled with me know that I make ambitious travel plans, so having a room that far from the action was not a good choice.


Then, as if that was not bad enough, on the second day of our trip Jamie came down with the flu. He might have mentioned something about "not feeling well," but I was way too excited about the schedule I planned to have heard him. One of the things on my list was a two-hour walking tour of the neighborhoods of Beverly and Morgan. These neighborhoods, which are actually part of the city of Chicago, offer some of the finest examples of Craftsman style, especially Frank Lloyd Wright, architecture in America. The architecture is the primary reason I chose Oak Park, rather than just booking a hotel in the City.


Jamie never complains, but after several blocks of walking on our two to three hour guided walking tour, Jamie did not appear to be doing so well. In fact, at one point, I think he might have laid on the sidewalk to take a rest. He also seemed to be sweating profusely. Not wanting to admit he might actually be sick, I figured it was just the brisk pace at which we were walking. We went back to the bnb, and I truly hoped that by dinner he would be back to normal. So, we hurried off to the restaurant where I had made reservations. By now it became clear to me, as Jamie sat at the white table-clothed table with his head resting on it, that the trip was rapidly coming to an end. After I cried a little and begged him to "try to feel better," we went back to the bnb. Within hours, I was now feeling the same flu symptoms and we both had no choice but to simply lay in the bed of our beautiful room in this historic home, sick as dogs with no cold medicine. We were too sick to even try to drive home. We finally did drive home, though I honestly have no memory of it.


So, September of 2005, not wanting my poor planning to leave us with bad memories of Chicago, I decided to buy a travel book about Chicago before I made any plans. After a significant amount of reading, and being a sucker for all things with a bit of history, I booked us at an historic hotel in the heart of the City. It was the Congress Plaza Hotel, built in 1893. I love history! This is perfect! Conveniently located on the south side of Chicago, and only a 7-minute walk from the Art Institute! Perhaps I did not take into account that travel books never tell you advice in a practical manner, because if they did, this book would have said, "Hey, dummy--stay out of the south side of Chicago, and don't stay at the Congress Plaza Hotel."


Before we left, my colleague recommended that Jamie and I go to Buddy Guy's Legends, a blues bar. He cautioned me, however, "Take a taxi, because this bar is in a really bad part of Chicago." When we arrived at our hotel, we noticed that it could have used a little freshening up. We pretended not to see that homeless-looking person hanging out in the lobby area smoking his cigarette and dropping it on the floor. I was not going to say one word; we were staying in the City! I was NOT going to screw up this trip! So, after taking the stairs to our room (because the elevator was broken), I hopped on the bed, got out my trusted travel book and said, excitedly to Jamie, "So, do you want to check out that blues bar tonight? You know, we'll have to take a cab because it's in a bad part of town... which, uh, according to my book it is, um, about one block away..." Oh, Chicago.


The Cubs or the Bears or maybe both (who cares I don't follow sports) were playing that weekend. We had enthusiastic sports fans running up and down the hallways and knocking on our door begging to be let in, because they were at the wrong room. Honestly, I don't think the hotel had been updated since 1893 when it was built. It was bad. We stuck it out though. We saw some sights, ate deep dish pizza, survived an almost mugging by a shoe-shine man on Michigan avenue, visited Navy Pier, and even made it to the Chicago Institute of Art for the Toulouse Lautrec exhibit. We survived, we had fun, but we can honestly say that we are in no hurry to go back to the Windy City.




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