The Bachelor goes to Chicago.

So for those of you who read Pablo’s recent post, I had the chance to spend almost a week in the Windy City. While I did get the chance to do some game, I mainly went to Chicago to check the city out. I won’t bore you with tales but instead just give my take on what I thought about Chicago and my observations on the city itself. Note that the only cities I have to compare Chicago to are Miami, Atlanta, and NYC since those are the cities I have spent a great deal of my adult life in.

While most of my Chicago trip consisted of doing touristy things, I did light amounts of game. From what I have heard, I went at a bad time as the weather just started to get cold. Here are some of my observations and takeaways of Chicago.

The people were genuinely nice and seemed happy.

A Chicago-native will not smile at you like someone in Atlanta would but their niceness is a lot more authentic as opposed to the fake nice you get in Atlanta. I found that even in sets, women gave relatively soft rejections as opposed to the harsh ones I am all too used to in Miami. From the staff at the restaurants we ate at to the Uber drivers, everyone in Chicago seemed to want to be there. I have never received better service in any other city (outside of a couple exceptions in Chicago).

In NYC, I found that everyone gave off an overcompensating vibe and was ready to yell at you on a moment’s notice. In Miami, the vibe is soulless with everyone wanting to shop for whatever the newest flashy thing is. In Chicago, I saw that people had places to be but were not as miserable about it. I was genuinely amazed at the midwestern hospitality and how real it was compared to the phony one you get in the south.

Very clean.

What stuck out to me as a long-time New Yorker is just how clean Chicago was compared to NYC. Who would have thought that you could have a nice skyline with massive skyscrapers and not have to smell radioactive waste on every block? Of the major cities I have been to, I have to say that the streets of Chicago were by far the cleanest. I heard on a date that Chicago has a way to get its garbage disposed of quickly instead of leaving it out on the streets like NYC would.

The crime seems very polarized.

Chicago is known for crime as a major city but my takeaway was that it is polarized. The dangerous neighborhoods in Chicago (famously the South Side) are perhaps more dangerous than dangerous neighborhoods in other cities. I am not going to post that crime is irrelevant in Chicago, it is not the safest place on earth. However, I found that it seemed to be polarized to where the areas that were bad were really bad.

Personally, I felt a lot less safe walking around in NYC after the pandemic than I ever did in my week in Chicago. I was in Manhattan and noticed that robberies were happening at some of the convenient stores I visited; despite them being in a safe part of the city. However, I would still caution anyone visiting Chicago to practice their street smarts as it is not exactly Boise either.

Better control on the homeless.

I am not sure what Chicago is doing when it comes to homelessness but in visiting the city, it seems to have the best control on the homelessness. While there were clearly homeless people downtown, some on drugs, they were not nearly as invasive as they were in NYC or even Miami. In NYC, you would have to deal with invasive homeless people ruining your meal outdoors or trying to harass you.

In Chicago, I noticed that areas of downtown that did have a homeless problem also had cops in the vicinity. I was having food and drinks outdoors with my date and one homeless guy was acting rowdy near us; police immediately handled him. I did notice one woman on drugs wandering around a block as well as tent city under a bridge but compared to other cities, it was not nearly as intrusive.

Social observations.

Now outside of the politics, I wanted to focus more on the social vibes I got from the city. Here were some of the things I noticed.

Pretty good nightlife with amazing service.

One thing I miss about NYC are its rooftop bars and Chicago had its fair share. I found that the crowds were more relaxed and the music wasn’t as loud as it would be at most NYC rooftops. The service we received was pretty good compared to dealing with snobby bartenders at a Mr Purple. Pablo and I met at a Happy Hour bar and once again, the service was great. I asked the bartender a question and despite it being a busy bar, he answered it with a smile on his face. Even the bar I had a date at was kind enough to tell me that they are short staffed and to make my order at the bar itself.

Arguably one of the best cities for dating if you are a minority.

Not even in NYC did I see as many black, Hispanic, or Asian guys with white girls as I saw in Chicago. In Miami, it is somewhat common to see brown men with white women (although it is likely both are Latinos) but Chicago seemed to have a lot of your typical American girl types with a guy from a minority group. In NYC, it was surprisingly not that common although things started to get better as the 2010s rolled on.

If you are a guy of a minority group complaining about dating in Chicago, I can confidently say that the issue is not your race. I noticed white women hanging out with a group of black and brown guys like it was nothing. In NYC, this would be somewhat rare unless you were in Manhattan and there is more segregation going on. In Atlanta, it would be quite taboo to see a white woman that looks good dating a brown or Asian guy.

A lot of abnormally tall women.

I was surprised at the amount of women I saw who were six feet and up in my time in Chicago. In no other city have I felt as short despite being six-feet tall myself (or half an inch or so away). As great as I think Chicago is, I think that shorter guys will start to feel insecure in the city. I saw a lot of guys who were easily 6’2 and up when I was out in the city. Perhaps it has to do with the Scandinavian genes that run rampant in the midwest.

Quality of women was above average but other cities are better.

Maybe it is the time of the year I went but I do not think that Chicago is in the same league as Miami or NYC when it comes to the quality of women. However, I still put Chicago above Atlanta if you are into anything but black girls. Chicago is good for any guy that loves white American women and that is perhaps the one category where I think it can beat out Miami and even NYC. One asterisk here is that I did visit the city in what is considered a bad time of the year so another visit might be warranted before I make a final verdict.

Closing thoughts.

I am still fresh off my visit from Chicago. In the future, I might write more about my time in the city!

6 thoughts on “The Bachelor goes to Chicago.

  1. As someone who lives in Chicago. this article seems very accurate. Midwest girls certainly aren’t as attractive as those in NYC and Miami but they are geniunely sweet and caring. You won’t find drop dead stunners here but you will find a lot of cute 7’s.

    1. Thank you for your input. I think Chicago could have some 9 or 10 potential given how the upper midwest has a lot of Scandinavian descent women and those are typically real good looking, unless Minneapolis kept all of them lol

      1. Chicago is literally 3 times the size of Minneapolis so it would make sense that there would be a higher concentration of hot women here. But it seems that they’re kinda rare here compared to NYC. Even on a night out in River North I would see maybe 1 or 2 8’s at best. But the women are much less pretentious here than NYC or LA, that’s for sure.

  2. Yeah I guess NYC and Chicago women are less pretentious than LA and Miami. But NYC has a much bigger modeling industry, hence why the women there are better looking than in Chicago.

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