Let’s get something straight right off the bat. Chicago is cold. I don’t mean that as a slam on Chicago, but I thought that you should all know that as I form my opinions of Chicago, the city, the ecosystem and the startups, in the back of my mind all I’m thinking is: it is cold here. Very cold indeed.

Now, the people of Chicago don’t seem to understand this. Everyone is telling me that the weather is beautiful, and that I’ve arrived at the perfect time to enjoy “the Spring.” Let me tell you something, Chicago. If you think it is nice out right now, even “nice for Chicago at this time of year,” you are out of your mind, and there is no coming back.

For comparison, let’s look at where I came from. I arrived on Saturday, after flying in from Florida. As I was on the plane in Florida waiting to take off, I received this picture from a particularly cruel family member:

It was 85 degrees.

It was 33 degrees when I landed in Chicago. And snowing. (For comparison, this is roughly what it felt like. That’s Rahm Emmanuel welcoming me to Chicago, by the way.)

Now, I’m no stranger to the cold. I lived in upstate New York for years, and after that I lived in Iceland. When I say that I understand cold, I really do. When I say I understand wind, I really, really do.

So when I say that Chicago is cold, you have two options. You can think, “Hey, he is just not used to it anymore,” or you can think, “Hey, it must be pretty cold up there.” When leaving Florida, one thing I hadn’t considered is just how cold Chicago would be. Know how people say Chicago is “the Windy City”? Guess what, it’s not just some metaphor for something. Turns out, Chicago is actually, well, windy. I know. BREAKING.

Which brings me to my current dilemma, the lack of a scarf. As I live in Florida right now (and spend a significant amount of my time outside of Florida in other warm places like Arizona and California) I didn’t consider the wind, and didn’t consider the cold. So I didn’t bring a scarf. Which is a bad thing, because I don’t exactly have the strongest lungs. Not asthma, but something more along the lines of a general annual attraction to bronchitis, with infrequent flings with pneumonia. Needless to say, I should have brought a scarf.

Now, take this disposition to respiratory disease, and combine that with the fact that the head honcho, Sarah, mandated/ruled/decreed/ordered me to couch surf. “It’ll be fun!” she said. “You’ll get a real feel for the city!” she claimed. Learning of my new adventure, and likely in on the charade, Greg and Erin both whole heartedly approved of the measure.

Little did I know, couch surfers are not as reliable as hotels, or even as reliable as the sand on the beach. (Can you tell that my mind is elsewhere, as I write this?)

Sure, the first few nights were great. Interesting people, comfortable couches, nice locations. Oh. But then things changed. Boy, did they change.

Probably sensing that I would turn on the city at some point and point out something bad about the technology ecosystem or one of Chicago’s startups, my scheduled hosts dropped me like a bag of potatoes.

“I’ve got to leave town.”

“I can do one night but not two.”

“Something has come up.”

Sure. I get it Chicago, you don’t like my insinuating that the people at the Jackson subway stop are insane strange. But kicking me out in the cold? Seems a bit harsh.

Now, if you’ll recall, dear reader, I am also disposed to bouts of lung-related illness. So, while I am traipsing about from host to host — nightly, mind you. I have to change places nightly — I am carrying a duffle bag, a laptop bag, and a not so nice virus. Which makes for an interesting story, sure, but also a rather painful experience.

You can see the picture. Little old me, barely hanging on to the railing on the trains. Coughing up a storm. At one point I imagined myself on crowded train in India, and by comparison I started to feel a little bit better.

But not by much.

As if all of this wasn’t enough, let’s focus our attention on something that is patently absurd. (No, not the patent system, though I understand the confusion). While I was living on the streets without a place to stay and slowly recovering from my illness, Sarah decided to allow me to stay a couple of nights in a hotel, which is great. Guess what I found out about Chicago? Approximately 90% of the hotels here require you to be 21 or older to check in.

Yes, I know the reasons. Drinking laws, mini bars, etc. Great reasons, really. If I’m willing to pay money though, I should be able to stay wherever I want. I should, and everyone knows this. Everyone. I honestly can’t think of a reason why someone would disagree with me on this. One hotel that I stayed at was 18 and up, and although they had a mini-bar, they just took the alcohol out of the room before I went up. Excellent strategy. Let’s all do that one.

While it may all seem doom and gloom, it isn’t all bad. The entrepreneurs are great, the ecosystem is better than I expected, and everyone is so helpful that I’m pretty sure I have the connections to run for mayor.

Not that I’d want to though, because it’s cold.

And you probably need to be 21.

[Image Credit: Shutterstock]