Chicago: The Windy City, Indeed


doesn’t mean the streetsand boulevards are densely populated with shops and restaurants; if anything, in a lot of (the more affordable) neighborhoods, it’s entirely the opposite.

So it should come as no surprise that I, a Los Angeles native, hate that I spend so much time sitting in a huge metal frame on wheels, disconnected from everything and everyone else around me; it’s just so isolating. And sure, people are friendly here, but I still find it difficult to just strike up a conversation with someone out of the blue because it’s as if human contact has become a foreign concept here. I blame the car-centric lifestyle. I don’t know, I guess I may have been spoiled; New York City was my introduction to what “city life” could (and should) be, after all.

And before this trip to Chicago, I truly believed that New York would forever be the only place for me. Naive, aren’t I? New York is so outspoken, unapologetic, loud and stimulating. New York City is an animal, but once you grow accustomed to it’s many nuances, you either come to love it or totally hate it. And I absolutely loved it.


Chicago, you just may have stolen my heart. I must admit, when I first booked this rather impromptu trip with my mother, a part of me felt just a bit disappointed that we weren’t going to be visiting New York City.  Despite having been born and raised in Los Angeles, a large part of me has never felt entirely “at home” in this city. Sure, we basically live in sunshine all year round and the beach is only a twenty-minute car ride away (at least from where I live), but aside from that, I’ve always found Los Angeles to be rather… dull.

Without a doubt, Los Angeles is an incredibly unique city, thanks in part to the fact that it is designed, and therefore functions, so different when compared to most other metropolitan cities around the world. Geographically, the actual City of Los Angeles is massive, expansive, and tied together by freeways that are always being repaved or rebuilt entirely. And we spend such a great deal of our time every day cruising along (if we’re lucky!) in our cars instead of walking about on our own two feet! Granted, even if we chose to walk, where would we go and what would we see along the way? Los Angeles is geographically large, yes, but that 


So how does Chicago tie into all this? Well, from what I witnessed and experienced in my five days there, Chicago proved itself to be the most perfect “hybrid” city I’ve ever seen. It’s an incredibly walkable city, and the architecture is awe inspiring! The Windy City’s urban landscape showcases a striking mix of  ultra modern, unadorned, sky high buildings side-by-side with a more traditional, warm and brownstone style architecture. Definitely a visually enticing mix! Oh, and the streets are remarkably clean! Seriously, I was quite shocked at how well-kept the city was! (New York, mayyyybe take note.)

That’s primarily the reason why I call Chicago a “hybrid” city. It’s too clean to be true! You don’t really smell urine or garbage everywhere you go and that, for me, is both amazing and somewhat confusing, hehe. Okay, but before this turns into a conversation about foul scents and their correlation to city life, let me just take you on a quick tour through my week of fun and long overdue relaxation.


Day One was and forever will be known as “Travel Day.” Somehow, no matter how often I travel, Day One is the absolute worst; I’m frequently overtaken by exhaustion since I’m too excited the night before to properly fall asleep, leaving me far too hungry and irritable on the actual day of travel. It’s pretty safe to say that my flight to Chicago wasn’t any different (just ask my poor travel partner, better known as my mother!). But if there’s one thing that’s actually quite fantastic about the trip, it was that it only took about three and a half hours to get to our destination. It’s really so quick! Three and a half hours and we went from being in 105 degree summertime weather to a cool 74 degrees and wind, wind, wind! It truly felt like the seasons were in a state of transition in the Midwest, like fall really was just around the corner.


That’s probably why my mother and I opted out of resting when we first arrived at the Thompson Hotel and instead dropped off our bags and decided to go for a very long walk. Luckily, both of us were very familiar with the metropolitan landscape and lifestyle so it didn’t take too long for us to get used to the “city vibe” that Chicago was emitting. All the walking, the weaving in and out of hoards of people, the constant stimulation of everything around us, it was all too familiar and we loved it! So what did the two of us decide to do on Day One?

We Shopped.

A Lot.


But, if you can believe it, the shopping wasn’t even the best part. Don’t get me wrong, I, like any other person, love to buy new things for myself, but Chicago has a lot more to offer than just shopping.

Like the River Architecture Tour, for example, which takes you around the city by boat (for about $40 a person) while a tour leader fills you in on the history of the city, one monument at a time. Chicago is a beautiful mix of modernity and Art Deco. While individually striking to look at when walking around on foot, the buildings create an entirely different experience when you see them all woven together, while floating by on a boat. So, if you’re an architecture buff, Chicago is, without a doubt, a great city to visit to get your fix.

Aside from the shopping and the River Cruise, however, another “must” on our list was visiting Millennium Park, home of Cloud Gate (also known as “the Bean”). Walking through Millennium Park, I got the feeling that this was Chicago’s equivalent to New York City’s Central Park; it certainly seemed popular enough to be (there were literally three different brides running around the park that day with their respective bridal parties)! So, yeah, if you’re a fan of nature and sight seeing while taking relaxing strolls, add Millennium Park to your list of to-dos!


Despite the short recap, I can honestly tell you that Chicago really stole my heart. My brief recount does not do this incredible city justice. Chicago is full of so much life, history, and of such rich culture, I’d seriously be crazy not to make another visit!