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Chicago, IL






The next stop in our trip between North Jersey and Denver was Chicago. After another ~400 miles, we arrived at the Windy City and here is how my boyfriend remembers it:





Chicago, IL


"The morning, the emotions of yesterday behind us and nothing between Cleveland and Chicago. It’s not quite the emptiness that enveloped the rest of our journey to Denver, but it’s not far off. Route 80 is a vast empty wasteland of farms and tolls, I don’t mind paying tolls when they lead to somewhere like Manhattan, but paying a toll when there are more cows then people kind of smarts. What choice do we have? It’s not like there was an alternate way to go that wouldn’t involve  driving down some back road that would take thrice the time.

We have a relatively short 400 milers trek from Cleveland to the second city, it’s late April so the weather in Chicago was much less likely to suck. We enter Illinois, stop at some generic outlet mall, one of those outlets that some company has built in every state…America land of the free, home of the same crap everywhere. We finish shopping slightly overwhelmed by the intellectual malaise that a generic outlet mall can cause your brain to have and head to the windy city, it was actually sunny but pretty damn windy.

The lady had been talking about Bucca di Peppo for months, why she would want to consume thin crust pizza from a small Italian chain when heading to the land of thick crust pizza still baffles me a bit,but we head into downtown Chicago for some anyway. It’s like going to Boston and stopping at Red Lobster for some chowder.  Lunch was good, not wonderful, stellar or even fantastic, just good. Another meal that I could have had anywhere. Alas, it was nice to be full of food and some beer.




We end up on the lake front and it’s windier than my bedroom when I used to eat White Castle at 3am drunk off of my arse from drinking Bass all night. It was that windy, the type of windy that would blow off John Travolta’s toupee. A very nice man and his wife volunteer to take our picture as we struggle to keep our eyes open and keep blowing sand out of our corneas. Next stop, the friendly confines.












The Cubs had an afternoon game that day, I thought about getting tickets and leaving Cleveland really early to finally catch a game at Wrigley but remembering that the gf once described baseball as, “You sit around, get drunk and nothing happens.” I decided that I’ll just fly back one day to catch a game. It can be 40 years from now and the Cubs still will not have won the World Series, damn stupid curse of the Billy Goat. Wrigley is an amazing place from the outside, bars are filled with intoxicated fans that either are unemployed or just like taking off weekday afternoons to watch a perennial loser. I’d be drunk too if I had to watch the Cubs regularly.  Stands adorn the tops of local apartment buildings and condos. Wrigley is truly charming, sitting right in the middle of a neighborhood, the scoreboard visible from the street. Flying high atop the rear of the stadium is a flag with a big L,  surprise, surprise the Cubs lost, somewhere, the man that once said, “"Booze, broads, and bullshit. If you got all that, what else do you need?" Harry Caray is mad and likely snatching a beer from God’s six-pack. After seeing one of the true treasures of America from only the outside, it’s time to head to the Sweedish icon of shopping, H&M.










She described this H&M as her favorite, and that’s saying something for someone that stops in every H&M she comes within a time zone of.  I have no idea what happened inside, I’d sooner spend my day in a dumpster with Eric Roberts then spend my lone day in Chicago indoors marveling at Swedish fast fashion, I leave her to her shopping nirvana and wander the streets. Tulips were everywhere, finding this odd considering I wasn’t in the Netherlands or even high enough to think I was, I find a sign in the Chicago area known as the Magnificent Mile that tells me that there is a Tulip exhibition from Holland. I secretly like flowers, I don’t brag to my other man friends that I do but alas it was pretty darn neat.  


{H&M - 840 North Michigan Avenue # 1, Chicago, IL - (312) 640-0060
980 N Michigan Ave # 1820, Chicago - (312) 255-0818}

After she loads up on bags filled with underpriced clothes made in a sweatshop far from Sweeden we head for some dinner, actually we skip right to desert and head to Ghiardelli. I have no idea what I consumed other than it was some fattening mouth-gasm with Carmel that I can only say was friggin fantastic. We stare longingly at each other and then feel our lack of nutrition overwhelm our energy levels and waddle back to my truck to drive to the hotel. We didn’t stay anywhere fancy that evening; her company is too cheap to pay for any hotel anyone would be proud to say they are staying at. Fat, happy and exhausted we fall fast asleep." 








The Boyfriend




Here is our original itinerary:




Day 2: Chicago, IL
Miles: 400
Hotel: Best Western Oakbrook Inn
669 Pasquinelli Drive, Westmont, IL 

Lunch: Buca di Beppo
521 N. Rush Street. 312-396-0001

Aurora Outlet Center
1650 Premium Outlet Blvd #1137, Aurora, IL - (630) 499-9569

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