Independence Day: Drunk And Homeless In Chicago

Homeless In Chicago

We are less than one week away from our great nation’s birthday. And with every July 4th that rolls around these days, I’m always reminded of the one ill-fated Independence Day when I was a homeless vagrant.

Early on in my post grad life, I lived in western Michigan (I’m pointing to the exact spot on my palm right now). I had a few friends from college that lived in Chicago, and I’d regularly escape the mitten to party for the weekend in Chiberia. I was looking to make such a trip for the 4th and it just so happened that my friend Emma was doing a summer internship with an accounting firm downtown. Her boyfriend Scott, who was my fraternity brother, was flying in to see her for the weekend. Perfect, I thought. They’re two of my closest friends and are also a fun couple to third-wheel with. Seemed like a no brainer to me, so I texted Emma to count me in for the weekend.

Bright and early on the morning of July 4th I made the two-hour drive over to the Windy City. Emma was staying in employee dorm housing in The Loop, so once I found the place and paid a cool $45 for 24-hour parking, I took an Uber to meet up with her and Scott at the beach. When I showed up, it was apparent that I was in last place in the drunk competition. Scott immediately threw me an ice cold John Daly in a sippie cup because God forbid you spill your drink in the sand. What happened over the next 12 or so hours is fairly irrelevant. All you need to know is that the drinking continued throughout.

Fast forward to 1 a.m. and we three amigos were out at a bar in Old Town. It’s a pretty douchey bar but it’s always full of hot girls so I demanded that we end up there. As fate had it, I walked out of the bathroom there and ran into my hot next door neighbor from Michigan. Her name is Steph. She was the last person I expected to see at this place, but it turned out that Steph was in town visiting some friends as well. My night had just gotten very interesting, and the play with hot neighbor girl was setting up perfectly.

I introduced Steph to Emma and Scott and suggested we all go to a different bar. In typical post grad fashion, Emma and Scott hit the 1 a.m. wall and decided they were going to bail. I of course was going to stay out with Steph and her friends, so Scott told me to give him a call later if I needed to be let into the apartment. No need to dive into the exact details or missteps here, but basically I botched it with Steph that night. It happens. At 2 a.m. she called it a night and went back home with her friends. Can’t knock the hustle.

At that point, I was alone with no choice but to shut it down and Uber back to Emma’s apartment. When I got there, the security guard wouldn’t let me go past the lobby, so I called Scott for him to come down and let me in. No answer. I called again. Voicemail. I tried calling Emma a few times. Nothing. I called Scott again and again and the grim reality of the situation began to set in. I bargained with the security guard to let me, some drunken stranger, exchange my ID to go upstairs and knock on the apartment door to wake them up. I knocked for a good 10 minutes loud enough to wake up the entire floor except for the only two people that could’ve let me in. Reaching maximum frustration levels, I headed back down to the lobby, bargained some more with the guard to let me use the bathroom, and then returned to my strategy of phone calls. The next morning Scott and Emma would laugh at me and show me that they EACH had 50 missed calls from me. I was desperate.

It was now around 3 a.m., the security guards had changed shifts so I came up with a fun idea and said, “Screw it, I’ll just stay up all night alone in Chicago.” This plan was cool for about 15 minutes. I left the building and started walking aimlessly down the street. For those who aren’t familiar with The Loop, at 3 a.m. it becomes a very lonely and a very scary place. The scene was me and about six homeless people within eyeshot each chilling hard on our respective street corners. These dark streets were no place for a 160-lb. Caucasian male at 4 a.m., so my next brilliant idea was to Google ‘24/7 bars Chicago’.

I figured I might as well just keep drinking until the sun came up. The results of that Google search were worthless and mostly strip clubs, so I decided I’d rather take my chances on the streets outside a 7-11.

Completely out of my element, I was peacocking way too loudly with my Polo button down, chinos, loafers, and inebriated gait. The night crawlers were eyeing me, and some began following me. Slowly but surely, I began fearing for my safety so I pivoted again to a new plan. It was an absolute miracle that at 4:30 a.m. my phone still had enough battery to Google map me to the nearest Hampton Inn. With no Ubers or cabs working that late, I hoofed it about 15 minutes to the hotel.

I walked through the automatic doors into the lobby and started feeling human again within seconds. The front desk clerk gave me the most judgmental look I’ve ever received, and when I asked for a room he said, “Of course. That will be $185.” I was going to pay that $185 no matter what, but considering I’d only be using the room for about 4 hours, I wasn’t looking to get swindled.

I tried using my tactful negotiating wit and told the clerk my girlfriend had kicked me out of the apartment after a big fight, and I just needed a place for a few hours so to please have mercy on me. Stonewall Jackson said no dice. With that, he left me no choice but to whip out the big guns, so I showed him my Hilton Honors Silver status and demanded that I be given a discounted rate. This guy was a pro. He was probably back-to-back employee of the month because he just told me to, “Either pay $185 or leave.” Those words are forever etched in my memory.

I handed him my credit card while mentally running the numbers of the future budget cuts I’d have to make. I took the elevator up, swiped my key, and collapsed on top of the king size duvet around 5am. 9am came quickly when I woke up to a text from Scott asking where I was. I took a picture of the wet bar in my king suite hotel room and sent it to him with a “Fuck You” caption.

I ate my free continental breakfast and coffee and then walked back to Emma’s place. As I entered the lobby, the security guard recognized me and we stood in silence while Emma came down to let me in. I don’t know why, but right before I got on the elevator the guard said to me, “Don’t forget to validate your parking.”…I just laughed and thought to myself, “Thanks guy, good lookin’ out.”

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