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What started out as an innocent suggestion to go see Bill Maher in Chicago a few months back turned into a reality this past weekend. That’s right I found myself in the middle of a megabus at 9 in the morning heading for the only city in a 1,000 mile radius that could call itself an international city. That was one of the things that I took away from this trip (along with the sobering fact that some homeless people will threaten to kill you if you don’t give them some change, but more on that later). Ever since traveling through Europe every new destination is seen through that prism, and in many ways Chicago made me feel like I had stepped back onto European soil. From the throngs of tourists to the little corner cafe’s and restaurants everything about the city had a very friendly feel to it. Walking 10 hours a day also took me back.

Lets start at the beginning though. I arrived in Chicago around noon on Thursday to what seemed like a 150 degree day outside. I was met at the bus stop by my friend Leer who dealt with the heat by both taking his shirt off and then putting it back on repeatedly. This was Chicago after all so no one seemed to notice the shirtless man walking through the city and he even had some company with a couple other people who “got it.” The heat in and of itself wasn’t too bad but the big bag that I brought did not help the cause. I think I tried to hold that bag in every way possible trying to find the one comfortable spot (there may have been a five minute window where my forearms weren’t stretched out.) Well after about a 20 minute walk in which it felt like Leer was trying to keep me from knowing how to get to his apartment ( every time I thought we were going to turn left down a street he would at the last second turn right,) we got to his apartment. When I stepped into the room I was greeted by an enormous window in the main room that opened to an amazing view of the Chicago Skyline. This was both the best and worst thing about his apartment, because this would also be where I would sleep every night and wake up around 6 in the morning due to the sun coming in. I think I deserved to wake up so early each day after I confidently told Leer that I can sleep through almost anything and that the sun wouldn’t bother me. Pride is a funny thing.

Chicago skyline

This was the view out the window

After resting for a little bit we decided to head out to Navy Pier for lunch. Navy Pier was probably my favorite part of Chicago and how can it not be. Any place that can have both a stained glass museum and a Jimmy Buffet’s margaritaville is ok in my book. In all honesty I had one of the better meals I’ve had in a while at a little greek fast food type restaurant at the pier. Maybe it had something to do with my love of gyros or the fact that I hadn’tNavy Pier Beach had anything to eat since that morning, but something about that meal hit the spot. From Navy Pier we walked to the beach and up Lakeshore drive. It is pretty cool to have a beach surrounded by skyscrapers so another point for Chicago. We decided to stop for gelato after working up an appetite walking for about an hour. I don’t think i’ve enjoyed an ice cream as much as this one since I was in Italy. The cafe we stopped in was called the Leonidas Cafe and they may have the best tiramisu  gelato this side of the Mississippi. Why was it amazing you ask? because not only did the gelato taste exactly like a perfect tiramisu, but it also was stuffed with real lady fingers. I think I may try to recreate this gelato with a tub of breyers coffee ice cream and some twinkies. From there we took the red line to Wrigley. As a sports marketing student I found it shameful that I had never seen Wrigley field so I would not leave the city without seeing it. Not only the field but the area was very historical. It doesn’t even matter that I really don’t care about baseball it was just one of those things you have to cross off your bucket list.

Wrigley Field

So this is where the magic happens?

After an hour or so of walking through Wrigleyville we walked to the Lincoln

Chicago Skyline

The view from the Lincoln Park Zoo

Park area. This was one of the more beautiful areas of the city so we stopped to explore a bit. We came to the entrance of the Lincoln Park Zoo and debated for ten minutes whether it was free to go in or not. Thanks to technology and my iPhone (you’re welcome for the free plug Apple) we found out that it was in fact free. What we didn’t find out however was that the zoo closes at 5. It was 5:06 so our trip to the zoo consisted of seeing a leopard in a 200 degree zoo house lounge on a rock not wanting to move for fear of dying from heat exhaustion. There were also some great views of water tanks with no animals in them. What I can’t figure out is where all the animals go when the zoo closes, but I’m sure I just gave Kevin James an idea for his next big blockbuster. From the Zoo we took a taxi to Pequads, yes that Pequads, a staple of the Chicago pizza scene. I decided to be blasphemous and get a thin crust pizza while Leer got the traditional deep dish Hawaiian. The pizza was awesome, so awesome that I could only eat two pieces which left me with an amazing breakfast the next morning.

Lincoln Park Zoo

One of the only "animals' we saw at the zoo

 The next day we set off through the city once more. We walked down Michigan Avenue only to discover that walking in front of us was none other than Kelsey Grammer aka Frasier. Little known fact Grammer made $1.6 million per episode of Frasier. Thats pretty remarkable considering no one watched the show. We thought we would follow Frasier, wouldn’t you too? He

Kelsey Grammer

My best attempt at snapping a picture of frasier

was with what looked like his daughter at first but after the open mouth kiss I wasn’t so sure. The best part about the whole thing was seeing peoples reactions to him. There were people who just walked by and didn’t notice him at all as well as people who walked past, stopped, thought for a second then did the whole look back realizing who had just walked past. My trip in Chicago was complete because I had seen a C-list celebrity.

From there we decided to take a boat tour of Chicago’s main landmarks. This is all part of my plan to take a boat ride in every city I visit. I learned much more than I ever needed to know about Chicago’s architecture on the Wendella boat tour. For example did you know that Chicago had an ordinance that no buildings could be built on land past Lakeshore Dr.  But there is a skyscraper past Lakeshore Dr. because the developers claimed that it was built on a landfill fill not land. So as our tour guide said always remember to find the loopholes in life. The tour was pretty cool however as we were able to see the city from a different perspective. It was also a good deal as the tour was an hour and a half for $26.

That night Leer and I went to a “soiree” hosted by Immerman Angels an

Lake Michigan

The view from the Yacht

organization that brings Cancer survivors together with people who currently have the disease. Having had someone in my family die from cancer I think this organization is a great way to help someone going through the disease. The event took place on a small yacht parked in the harbor of Lake Michigan. I thought I should look my best so I braved the 100 degree temperatures in a suit. Not one of my better decisions considering I stuck out like a sore thumb compared to everyone else who was more smartly dressed in shorts and polos. It was all worth it however when I was told my tie looked dapper, whatever that means. In all honesty the event was a great cause that sought to raise awareness for the organization.

The next morning we walked to the bus station to pick up our friend John who would be going to see Bill Maher with us. Along the way we stopped to marvel at the world’s greatest technological feat, The Bean. The bean is the one thing in the world that can unite both little kids and frat guys who both can’t wait to take a picture of their reflection. Once we left the bean we walked by a hotel that had a crowd of people gathered around it. We crossed the street to see what all the excitement was and this is what we saw:

It was either an Indian wedding or this boy’s super sweet bar mitzvah. Only in Chicago does this sort of thing happen. When we picked up John we decided to go to the Chicago Institute of Art. There was a lot of great exhibits such as the one

medieval weapons

Which one would you choose?

on miniature rooms and houses. The amount of detail that went into these little models was amazing. You could look through the windows of the house and see outside in the yard which looked as realistic as a true house. We also walked through an exhibit on medieval weapons which led to a 20 minute conversation on which weapon you would choose for battle. These types of conversations are only too common when in the presence of John. We left the museum and tried to decide what to do. I got the bright idea to walk to Soldier field which turned out to be one of the dumber things I have ever come up with. First of all I thought that Soldier field would be another great stadium to cross of my list, but with its new renovations its hard to tell that it has any historical significance at all. At the same time Manchester United was playing the Chicago fire inside the stadium and we happened to walk there right as the game was over. So in essence I got us stuck in traffic with 80,000 people to take one picture of a futuristic looking steel stadium.

The last part of the trip involved going to see Bill Maher at the Chicago Theater. Even though I had heard most of the jokes that he told I thought Maher did a great job of connecting with his audience. For a two hour show he was able to keep everyone laughing and engaged throughout. No matter your political persuasion its hard not to give Maher credit for continuing to stay relevant all these years. On the way back from the show we were fortunate enough to get hassled by not one but two homeless people in one area. The first was a lady who was talking about a mission she ran in the city, the three of us just kept walking so she took this as a reason to walk next to us and keep talking to us. The other guy decided that if we didn’t volunteer our money to him he would threaten to kill us. So my last night in the city consisted of getting threatened by a homeless man. So this would be how I would end my time on this earth?

Overall I loved the three days I was able to spend in Chicago. It truly is an amazing city that would take weeks to properly visit and dissect. It didn’t hurt that Leer was a great tour guide that was up for anything. This included trying to find an old church in the middle of the city that we could only see from afar. When we found it we found ourselves in the heart of Depaul’s campus. This is the way I love to travel, having no real plan in place, but just walking and finding things naturally. Here’s hoping that Leer and I have more travels like this in the future. Its nice to know that Chicago is just a 3 hour megabus ride away. For now enjoy some of my pictures from the trip, and I look forward to working with no breaks for the next couple months to make up for this 4 day vacation.

Chicago Theater

Garret's Popcorn

Marilyn Monroe

Chicago loves Marilyn?

BP Bridge

The Bean

The greatest thing in the world

Chicago Institute of Art

Chicago Institute of Art


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