I have read at least a dozen articles various people have posted about what to really do in Chicago, all of which were somewhat true, funny and in general, nice reads. As my project at work has just been submitted to QA, I have an hour or so of unanticipated free time, which I would hate to spend skimming through Reddit, StumbleUpon or worse, Facebook. Therefore, with a very productive mindset, I decided to come up with my own rendition of how to be a Chicagoan, based on the few years that I have spent here. Needless to say, many things will be skipped and perhaps some nonsensical points will be included. Some of my ideas will coincide with yours, or what you have read about, but some may contradict. These are merely opinions — so, just humor me.
Supporting a sports team from Chicago is NOT mandatory
If you are a sports fan and you do happen to support one, or all of the Cubs, Bears, White Sox, Bulls, Black Hawks and Fire, great. But even if you don’t, don’t feel like an outcast. Lots of us aren’t into sports at all, and being as diverse as Chicago is, most of us probably are from different places where we’ve established our favorite sports teams as kids, and continue to follow them. Chicago isn’t limited to the handful of sports teams that the city has, it is much more than that.
Make the “L” your best friend
It’s okay if you cannot drive, or feel intimidated by the traffic, the recklessness, the potholes — driving in Chicago is a miserable experience anyway (unless you like a 1000 dents in your car, and enjoy cracked rims every now and then). But you cannot be forgiven for not knowing your way around the city through its excellent public transportation system. This applies to CEOs and the homeless alike.
Explore places to eat out
Yes, Chicago definitely has some of the fanciest restaurants in the U.S. But unless you make a very fat paycheck, you will probably not get even close to them. What truly defines Chicago is the plethora of small, local and quite inexpensive places to chow down at. You will be pleasantly surprised at how many seemingly “ghetto” places will be the ones featured by the Food Network, or the Travel Channel, or has had top food journalists visit numerous times. So if you have been living in Chicago and eating at fast food chains, or saving your pennies for fancy restaurants, you are doing it wrong. Go out, and eat at the first local restaurant you see. You will be surprised at how good it will be. (Just make sure the first restaurant you see is not a McDonald’s)
This city prides itself in being beautiful. It was built from ground up to be pretty and picturesque. Go outdoors, and walk around, even if it is just a few blocks around your house. If you are lucky, you live near the lake, and it is even prettier. Take the “El” to downtown, then walk again. Even the best cities in the world do not have such a beautiful downtown, as the Magnificent Mile. But downtown Chicago is not just limited to that — it is a very beautiful and sophisticated concrete jungle. If you have not taken the architectural tour yet, do it. It is simply amazing.
If you live here, snow will become a part of your life — and that includes, freezing wind and snowstorms as well. Rather than constantly complaining about it, get a nice warm coat, some thick gloves and a hat, and get on with it as if nothing has happened. Almost everything you will have at your disposal during summer will still be there during winter, and in fact some more nice things like beautiful lighting and ice skating. Also, either learn to drive in the snow or befriend the CTA as I mentioned before, because trust me, people here will drive in snow, as if it’s 85 degrees outside.
Join groups and organisations
Regardless of who you are, you will have some interests, some hobbies. One of the best things about Chicago is that it offers an organisation you can join for any interest you may have. And the best part, it is almost always free. So make use if it, make new friends, and expand your network.
Chicago is an urban jungle, but it is not New York. People aren’t so busy that they won’t talk to you. Go to coffee shops to do your work. Say hello to a few people around. You will be surprised how friendly everyone is — if you are good at conversations, chances are that you will be invited to a party they are hosting the coming weekend. It is as simple as that. (No offense to New York, it is amazing in its own ways)
Know your nightlife
As much as it is beautiful to be around the day, Chicago has an amazing nightlife. Every neighborhood, has its own scene going on, from amazing drink selections, to live music to great nightclubs. Pick your stop, but don’t limit yourself there, hop around — enter some local college bars one day, or dress up for some fancy places another day. If you are a party animal, know what closes when. Pick your place to hangout till 1 am, then know where to hop till 2 am and then know where to go to party till 5 am. And if the Red Bull is still going on at 5 am, know where the after party is. If you cannot find one, create your own and invite people over. (Keep the next day free to recover though, and don’t attempt after parties on a weekday unless you are really feeling adventurous)
One word that sums up the city of Chicago is diversity. So be yourself, people will appreciate you for that. Don’t go overboard with patriotism so much so that you are wearing your national flag around every day, but don’t be afraid to represent. Represent your country, your nationality, your sports team, or just your views and opinions, while being respectful of others and you will be well-respected, too.
Even if you pick 1 new activity to do each day, you will have grandchildren before you run out of things to do in Chicago. So have fun, be abrupt, be spontaneous and be adventurous. That is the best way to live, feel and breathe the City of Chicago to its fullest. Enjoy!