Chicago is One Town That Won’t Let You Down

Lake Michigan and the Chicago skyline.

So it’s been a little over a week since I got back from Chicago, but I still think the pics, and the experience, are blogworthy, and therefore need to be posted.

Since my best friend Sam is now Dr. Sam, and began her residency at Rush Hospital June 28, it was only right that I go visit her before our friendship takes a four-year hiatus (Sam I miss you!). Her apartment, which lies right on the Chicago River, is sick, with floor-to-ceiling windows, granite counters and stainless steel appliances. Quite a move up from her’s and her husband Patrick’s one bedroom on Long Island. Congrats guys!

Mushroom and pepperoni goodness.

There were several things I had to check out while I was in town – the generic, “I’m going to Chicago” things that every tourist needs to do before they leave. Number one: eat deep-dish pizza. According to Sam, there’s only one place to do this and that’s Giordano’s. She warned me ahead of time that a small would be sufficient for the both of us, but, I’m a professional eater and didn’t take her seriously. Also, I’m on a health kick and had to get my serving of vegetables, so I forced Sam to order fried zucchini sticks. And I still made it through two pieces of pizza. Take that Chicago – I will not be outdone!

Next, we had to check out Lake Michigan, because I am amazed that something that looks like an ocean can be classified as a lake. The water seriously looked like it belonged on the coast of a tropical island, and in the hot weather, boaters were out in full force.

I have no picture-taking shame.

Also out in full force: weddings, and not the pretty kind. We had top hats, parisols, gangsta-pinstripes and Russian mail-order brides getting their pictures taken near the planetarium. There was also a sweet girl getting pictures taken for her quinceanera, however, her dress of choice made me want to vom.

After a few hours of walking around the city and checking out Millenium Park, Navy Pier, Michigan Avenue, the fountain from Married…with Children and the “Taste of Chicago,” I then made Sam take me to the top of the Sears Tower (now called the Willis Tower, how dumb).

On the Skydeck, there are 360-degree views of the city, and visitors can see as far as parts of Wisconsin, Indiana and Michigan. We could see Sam’s building, which looks even cooler up high, and I could also test my height-tolerance by walking out on the Skydeck’s glass floor. This was totally in preparation of my skydive!

Awkward Skydeck shot.

Finally, after a long two days of traveling, I crossed my last task off the list: buying a Chicago Cubs t-shirt. I loved being in a city where being a Yankee fan is not a mortal sin, and where my dates don’t judge me based on the fact that I’ve lived on Long Island.

While I would still root for my NY teams if the Cubs/White Sox/Bulls/Bears/hockey team I can’t name are in town, I do really like Chicago fans, who are as educated about their sports as they are about their deep-dish pizza. I was impressed by the t-shirt shop owner who gave a scheduling breakdown for baseball that made more sense than 1 + 1 = 2. Congratulations Chicago – your sports fans are a treat.

Boston, you need the L!

While I didn’t get to meet Kanye or Oprah, and I didn’t take a trip out to Wrigley Field or convince anyone to bring back My Boys, I had an awesome time in Chicago, a city at the same time familiar and completely different from anywhere I’ve been.

Sam and Patrick, I wish you the best of luck in your new city, and I hope Harry has adjusted to being left at home! I’ll be back Chi-town. Be prepared.

For more awesome pictures, click here!