4 days in Chicago

Before flying home, I took a quick little stop in Chicago to see what all the hype is about. The flight was also the cheapest way for me to get home so that was also a major factor in the timing of checking off Chicago from my bucket list (I have a list I made in 2013 that needs revisiting).  I’ll give a Bert description of my 4 days in Chicago but if you are at the airport trying to decide on a destination, go ahead and book Chicago.

People love Chicago. My brother goes every year. I haven’t heard anything bad except for all the murdering that happens. Apparently, the danger is more on the outskirts of the city so this Canadian was safe staying downtown. I didn’t have much on my to do list. My list included going to a country bar, wandering around the city, eating some famous Chicago hot dogs and pizza, taking part in the architecture tour, seeing a baseball game, seeing that famous bean thingamajig, and essentially embrace being in an English-speaking environment after finishing my time in Shanghai.

Let’s start with what I was most excited for: country music. I adore country music. Going to a country bar is much more fun that any other type of drinking establishment. They aren’t pretentious, they aren’t expensive and people aren’t there to start trouble. People are there to drink, ride bulls and listen to Alan Jackson songs. My theory is that people who like country music are much less likely to be murders. Prove me wrong; you can’t. So, here is what happened when I went out. First, if you are a guy and you go out in Toronto alone, people think you are super weird (which might be true) but in New Zealand people would invite you to their group. I was unsure where Chicago would fall on this continuum. Before making my dream come true and going to this somewhat famous country bar, I went to Guaranteed Rate Field to see the White Sox play the Minnesota Twins. Baseball teams have fun giveaways on the weekend and luck would have it that that Friday was COUNTRY NIGHT! Do you believe in miracles because I do. 

So, I take the subway out there, grab a few beverages, wander around the stadium, eat some unhealthy food and finally settle into some seats with hardly anyone around me. There did happen to be two married women behind me and I thought this would be a good time to approach strangers and pepper them with questions. My first question to them after confirming they had husbands was, "So.... is getting married a scam?"

I do not believe these women have ever been asked this question before in their lives. They had no reason to lie because their husbands weren’t at the game and they both agreed that it’s not a scam and that it was mostly about managing your expectations. I then rapid fired a few more questions before excusing myself and letting them enjoy the rest of their night sans Bert.

I take the subway south to Bub City and find there is a bit of a line to get into this establishment. I then come to the realization that Chicago is a bachelorette hotspot. The whole weekend, I am seeing groups of women in matching t-shirts drinking champagne and puking off speedboats. Whilst in line, a group of ladies from a bachelorette party ask if I’m married. My smooth response? “Ahhh I’m from Canada.” THAT’S NOT HOW WE TALK TO HUMANS BERT! 

Oh brother; we are off to a rough start. I get into the bar, order a drink and everyone in there is with friends and having a gay old time. I am not with anyone, drinking my gin and tonic just happy to understand what is going on around me. Then a lady who was in her late 20’s comes up and says her friend thinks that I’m cute and asks if I will join her and her girlfriends. If you can imagine, I joined them. It didn’t take that lady long to realize I am not as good looking or charming as she thought and I was soon left alone once again.

About 10 minutes later, a guy from the line I was in to get into the bar asks me if I want to come with him and his friends to another bar. Should you leave a place with a stranger you’ve never met? Yes, yes you should. However, I realized the bartender had my credit card so I had to decline his request after I realized this fact.

Back to being alone.

10ish minutes pass and a handsome man who was about 50 asks if I’m sitting at the table I’m next to. I said no so he calls his girlfriend over and only because he feels bad, asks me if I want to join them. SURE! I replied enthusiastically. So I’m sitting with this attractive older man with his lady who definitely has a biker chick kind of vibe who is blonde and slightly older than him. He’s telling me stories about being a musician and how much cooler her is than me. To show off, I told him I would go over to a pair of women and show him how smooth I can be. Long story short, I ended up buying these two people drinks then never talking to them again. Classic Bert move. 

Finally, alone once again, another lady waves me over and asks why I’m all alone. She’s from England and had a good heart but if we are being honest, I would have rather of been alone than talking with her so eventually the lights come on around 1:40am, I make my way to the local hamburger shop where the man working at the counter was by far the most interested anyone was in me the entire night. If only God made me another way, I would be much more successful in the love department. So that’s my Chicago Friday night country bar story.

The Saturday I did the Chicago architecture tour which was certainly worth it. I found it interesting that there was a man selling beer on the boat like they sell beer at a Jays game. Americans love boozing it. Here are some stolen pictures of the tour.

The biggest surprise about Chicago due to my limited research was how outstanding and expansive their waterfront is. It’s spectacular. People are biking, running and there are countless areas to jump into the water or find a nearby beach. Did I get lost going in the wrong direction? Yes. Did I take more than 41,000 steps? Yes. Did I find a massive beach volleyball event? Also yes.

A major highlight that my hostel recommended was a neighbourhood named The Pilsen. It’s a Latino community that has delectable food, creative street art and is not like the rest of Chicago. I went to Los Comales #3 and asked the waitress to bring me anything she thought was exceptionally good. She did not disappoint.  If you are interested in doing something a little off the beaten path in Chicago, it’s worth the quick visit. Also, I wanted to visit The 606 Bloomingdale Trail but didn’t have time but it is compared to NYC’s Highline.

Other notable mentions in Chicago was the 24-train system; I felt much safer than its reputation. Midwest hospitality/charm is a real thing. Chicago Riverwalk is a great spot for sightseeing, kayaking, coffee and drinks. Navy Peer is bustling and worth the visit even though this is where my getting lost confusion began so BE CAREFUL! Chicago has a crazy number of parks, has random street art, lots of museums but I have a no museum policy lately so I can’t give you advice on that but Chicago has lots of sports teams and music festivals to keep everyone happy. I left a few days before Lollapalooza took place.

The only real negative thing I can come up with is the high amount of homelessness around the city. I don’t know anything about the numbers or what the city is doing to improve the situation but there are people asking for change or food everywhere I went. It’s sad and disappointing to see that in such wealthy countries like Canada and America, people have to live like that. I don’t know what the answer is but it was the only downside to the trip.

I would most certainly advise you to go with a pal, co-worker or mistress because while traveling alone is fun, I’m sure hopping on a boat and exploring Chicago by water with friends would be even more more memorable. 

Also, I live in Korea now so you should be getting some Korea input soon. Let’s just remind ourselves that I didn’t like Thailand, New Zealand or Shanghai at first so let’s give this new spot some time.

“It is hopeless for the occasional visitor to try to keep up with Chicago-she outgrows his prophecies faster than he can make them. She is always a novelty; for she is never the Chicago you saw when you passed through the last time.” Mark Twain