10 Important Things to Consider Before Living in Chicago

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I have come to the conclusion that DRD4-7R is very prevalent in my genetic makeup. This combination of letters and numbers is the name of what has been dubbed the wanderlust gene. This is due to its ties to increased levels of curiosity and anxiousness, mainly.
I grew up in a small city in the Midwest, but I find myself spending a good amount of time trekking through the vast landscape of mountains and forest in the Pacific Northwest.

kayaking glacier national park

Before I made it to Chicago, I hadn’t been engulfed by many places that I could consider large enough to be a city. I have visited many cities, but never had the time to truly explore. When the realization came into effect that I was indeed making my way to Chicago for the first time, it was a mixed feeling. Excitement of the unknown was the first effect– followed by an overwhelming feeling when I really thought about what I was about to put myself through. Huge buildings, too much traffic, so.many.people.
The fear of the unknown and being out of my bubble was somewhat thrilling.

Stepping out of O’Hare International Airport and riding towards the city was exhilarating. Then all of a sudden Chicago’s mighty skyline appeared out of nowhere and consumed my eyes. It was intense. It was beautiful. It was confusing. I was having an internal struggle of love and hate. My love of the mountains and solitude was conflicting with the yearning to take on something new and surround myself with millions of people. The first time I stepped foot in Chicago was actually the winter of 2013/2014, so it was pretty miserable. I was having flashbacks to growing up on the plains. However, once the temperature rose and my exploration could begin outside, that is when the learning experience fully began.

1) Chicago has greenery.

After being in Los Angeles and seeing the never ending block after block of concrete with little vegetation– I assumed that was standard procedure. Nope. Chicago blew my mind with the amount of foliage that they have– from the parks, to the little sidewalk garden areas. The fact that there are phenomenal parks right in the downtown area is surprising– yet innovative. It provides a nice break from the fast paced concrete surrounding it. I also believe this has an effect on the city being so clean. Trash is put where is belongs. Kudos to management and citizens for that.

chicago park bike ride

2) The Waterfront is kind of majestic.

It’s very relieving to be able to go somewhere in the city and essentially stare off into nothing. With everything to your back, you can just… decompress.
It also does allow for some pretty stellar dock parties as well. When summer makes itself evident, and the beaches open back up– the waterfront is a whole other scene. With tiki bars and beach volleyball, it is Chicago’s own little slice of ocean life. Yachts and sailboats galore and with the Lakefront Trail being packed, makes for a relatively social scene.

rowboat in lake michigan

3) The food & drink scene is unfathomable.

I was well aware that Chicago possessed a massive culinary scene and arguably some of the best bars around– but it wasn’t until I was trying to navigate it first hand that I understood how huge it truly is. Everyone will point you in a different direction– and that isn’t necessarily a bad thing. Really, it’s like a scavenger hunt. For example, I love chicken wings– so rather than going to the same spot over and over, I aimed to try some place new as often as possible to see how they hold up. New distilleries, breweries and innovative restaurants make sure that the scene will never dull.

drink at g & o in west town

4) Chicago Dogs & Deep Dish Pizza– Oh yeah, Italian Beef.

These three items seem to be of all the rage when people thing of the Chicago food scene. Yes, yes, yes– they do play their own role and impact the scene. However, from speaking with many native Chicagoans– they all have their fond memories and certain occasions when they will indulge in these Chicago specialties, but for the most part it seems like a hot spot for tourists.  Feel free to prove me wrong on this.

pizzaria uno deep dish in chicago

5) Downtown is neat, but perfection lays just on its outskirts.

This is a obviously a biased statement. The clubs and whatnot can be fun, and perfection for some, but I enjoy the more laid back atmospheres. I like to be able to have conversation, I like good beer, creative cocktails, food with thought put into it and just the welcoming feel. According to many– I fall into the hipster neighborhoods then. I’m fine with that– apparently hipsters have pretty phenomenal taste and they know how to create cozy venues. West Town and Logan Square being two frequent stops. Plus, the people just seem more friendly. I enjoy stepping into a random bar that has the same vibe that I’ve encountered in a small town along my travels. If anything, it is a welcome change of pace from the typical Chicagoland fast paced setting.

marble bar in chicago

6) Chicagoans are pretty nice people.

For the most part, you can sit anyone next to me and I can hold a conversation if required. But, when it comes to the majority of people that I’ve had the pleasure of meeting in Chicago, conversation isn’t forced. You find a lot of people that are full of passion and charisma– it is inspiring. People also love their city and seem eager to point you in the right direction of places to experience. Without these personal recommendations, many spots would lay dormant to me.
I have met some pretty great people just from striking up random conversation at the bar– people that I still interact with to this day.

group of people in front of chicago skyline

7) Be open, be spontaneous.

It is nice to have guidance, but with so many opinions floating throughout Chicago, it can be best to create your own. If you are walking down the street and something catches your eye, go in and try it out. There are hidden gems throughout Chicagoland just waiting for you to indulge in them.
If I find myself in the greater downtown area, I try to avoid taxis as much as possible for this very reason. Being on foot or bike allows for you to fully take in your surroundings and stop in any shop whenever you’d like.

Divvy bike on Lakefront trail In Chicago

8) It’s okay to have a tourist day.

Chicago is a top tourist destination for a reason– weather that be for music, food, museums or a million other reasons. People flock to these locations for a reason; you may learn a thing or two. Tours are also a phenomenal way to see the city and learn some intriguing facts. Selfie with the bean, eat some popcorn, check out the pier and see where the day takes you.

selfie in navy pier ferris wheel

9) The automotive scene is quite impressive.

Chicago is full of wealth and full of passion. Depending on the level of automotive enthusiasm that you are at– those two traits are key. If you are a fan of supercars, head to the Viagra Triangle and the mass amount of money in Chicago will make itself very prevalent. Bentley, Lambo, Ferrari, Porsche– and a Maybach just drive by in a row. If you are lucky, a Mclaren will even make an appearance. About 50-miles from the Viagra Triangle you will find yourself at Autobahn Country Club. No, this isn’t a German inspired golf course– this is an automotive playground that allows you to push your car hard and fast. Even just spectating is quite a treat to the eyes and ears.
Being so close to the Motor City, the American automotive scene is quite strong (I expect). Honestly, I haven’t explored it much– as I tend to find myself gravitating towards Euro and Japanese creations. JDM Chicago is Chicagoland’s premiere outlet for this scene. Automotive features and event coverage are in no shortage. The high-quality level of builds in the area are inspiring. If you are in the mood to just cruise, be sure to head up to Highway 100 near Milwaukee. Everything from superbikes to supercars and every vehicle in between will make an appearance.

risky devils rocket bunny brz in chicago

10) Chicago has something to offer anyone.

With all of this said– I am still barely scraping the surface of Chicago. It really is that expansive. The city is a conglomeration of so many cultures and tastes that anyone will be able to find their niche. For the adventurous souls, there are plenty of opportunities to step outside of your bubble and grow.
If you are a city dweller– Chicago offers it all. If you are more of a rural soul that has found themselves in the city– it may be rough, but there are still ways to get in your nature dosage and some peace. There are some impressive locations for hiking and camping within hours.
As far as major cities go, this one right here may very well be the golden child.

lincoln park and chicago skyline at sunset

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Ross Perkins

Ross Perkins is the Executive Editor & a connoisseur of all things enjoyable– at least in his mind. He is an avid traveler in the name of inspiring sights, music, food & cars. He is a published photographer & writer that is looking for any reason to get out and explore his surroundings.

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