chicago is the actual best (not biased at all)

If you haven’t gotten it from reading any of the posts in this section, one of my all-time favorite things to do is travel to different cities and learn about different languages and cultures. I love traveling, and I am fortunate to have traveled all over the US, mostly in pursuit of an education. One of my dreams for this new blog is to write about the many places I go, whether in the US or the world. I figure that a good place to start for this indefinite travel series is at the very beginning, in the city where I grew up—Chicago.

Truth be told, I grew up in the suburbs, only occasionally venturing into the city with my parents or my cousins. I saw a lot of the most important sights—the Sears Tower (no local calls it the Willis), Millennium Park, Michigan Avenue—before college, but I never traveled into the city with any sort of frequency. It was only after college, when I came home for a gap year, when I started going into the city with any sort of regularity. And it confirmed what I had always believed: after all my travels, Chicago is still my favorite city in America.

Chicago is kind of like New York, but cleaner, less crowded and way more chill. As far as business opportunities, its many skyscrapers are bursting with them; the opportunities are comparable to pretty much any other major city in the world. It has world-class shopping, parks, sports and food, and it is one of those cities where you can come back again and again and discover more every time you come back.

Whenever I tell people I’m from Chicago, I get two reactions. People who haven’t been there (especially people from the Northeast) are usually scared for me, wondering about what they’ve seen on TV; the crime, the police altercations, the literally Antarctic cold. And don’t get me wrong, Chicago has a LOT of problems to sort itself through. But what’s telling is that whenever I have told someone I’m from Chicago, and the person has actually visited Chicago, their response is almost invariably the same: “Oh yeah, I love Chicago!” 

So, allow me to introduce you to my city and some of the best things about it.

The architecture

Strangely enough, one of my favorite memories of my gap year was driving into Chicago from my hometown. It always took a very long time because of traffic, but I was always elated when in the middle of the morning slog, almost as soon as I crossed the city border, that glorious skyline would come right into view, and the rest of my morning commute would be instantly more beautiful, if not much faster. Chicago has four of the top 10 tallest buildings in the US, and once you get into the city, you can see them all, along with many others, in near-perfect symmetry from almost everywhere you look. 

But Chicago’s architectural prowess certainly doesn’t end with its skyline. After the Great Fire of 1871 destroyed everything, I think the people who redesigned Chicago wanted to make the city architecturally stunning as revenge. The result is a whole lot of beautiful buildings, from skyscrapers to libraries to houses. I did an internship at was at a health center in a very rough neighborhood called Lawndale, but I found it telling that even the houses in that neighborhood were pretty and had a clear architectural style. We take our architecture very seriously around these parts.

The first photo is a stock photo of Chicago from Lake Michigan, and is not mine. The rest are my own personal photos. The second photo is from a plane; the third, fourth, and fifth ones are all from my friend’s apartment downtown. The fifth one is of Navy Pier. I took the sixth photo from the University of Illinois at Chicago, where I used to tutor students during my gap year. Click each photo to go through the gallery.

The sights everyone knows about

On a Saturday when the weather is fine and you don’t know where to go, Michigan Avenue is a great place to start. In just one mile on this road, you’ll see the Art Institute, Grant Park, and Millennium Park, as well as the most important sight: the one and only Nutella Cafe, right on the intersection of Michigan and Lake Avenue. All of that comes before the Magnificent Mile. The Magnificent Mile begins when you cross the Chicago River, and there you can find shops and restaurants galore. What I like about the Magnificent Mile is that it has high-end shops like Cartier, Zegna, and Hugo Boss along with lower-end shops like H&M and Zara and many, many more. I feel like a lot of people can shop on the Magnificent Mile; it’s more like Oxford Circus in London than say, Rodeo Drive in LA, which has only high-end stores.

Grant Park and Millennium Park are always busy. In the summer, for example, there are free weekly classical music concerts coming from an amphitheater; during the holidays, Millennium and Maggie Daley parks bring out ice-skating rinks. During my gap year, there was one weird week in February when it was 70 degrees outside. Because the ice-skating rink isn’t removed until March, my friend and I went ice skating in Millennium Park…on a near-summery day. it was weird and amazing.

Just behind Millennium is a new park, Maggie Daley Park. Apart from the aforementioned ice skating rink, which is less a rink than a path swirling through the entire park, Maggie Daley has multiple intricately designed playgrounds as well as multiple rock-climbing walls. 

The Art Institute costs money to get into, but if you’re willing to pay and if you like visual art, by all means, go! Aside from having beautiful paintings inside, the place itself is gorgeous, with pavilions so pretty that people even get married there. You can also get a pretty good view of downtown from the Nichols Bridgeway, a huge pedestrian walkway that starts near Millennium Park and takes you to the top of the Art Institute. 

DuSable Bridge, the bridge you cross to get to the Magnificent Mile; Nutella Cafe; one of the pavilions by the Art Institute; one of the two sculpted lions in front of the Art Institute (you can guess what day it was taken on by the hat); view of Jackson Street from Nichols Bridgeway. The last three photos are my own.

…and the sights you don’t know about

Everyone knows about the Magnificent Mile; it is the highest-grossing street in Chicago. But not a lot of people know about the second highest grossing street in Chicago, 26th Street. 26th Street is the central street of a neighborhood called Little Village (AKA La Villita or South Lawndale) on the West Side, and going there is literally like teleporting to Mexico. There are Hispanic grocery stores, quinceañera shops, mom and pop clothes shops and of course, tons and tons of authentic Mexican food shops serving everything from tortas to tacos, from quesadillas to paletas (the Mexican equivalent of popsicles, with much more natural flavor). I straight up got fat on my internship from coming to 26th Street so much. The only precaution: being that Little Village isn’t the nicest neighborhood, I would go only before sundown.

There are many other food streets like this in Chicago. Up on the north side, Devon Street is the place to get all the best Indian and Pakistani eats. Taylor Street on the West Side has four iconic Italian restaurants. Argyle Street is the place for Vietnamese food, and for those who like fine-dining, the West Loop and Fulton Market neighborhoods have become known as “Restaurant Row”. Like every great city, Chicago has a Chinatown with great Chinese food on the near-South Side. I should know more, but here is where my suburban-ness comes out; I have plenty more to find out myself.

While we’re on about food...

Did I tell you Chicago is known for good food? No? Well now you know.

In Chicago we like our pizza crusts a bit softer and more noticeable then say, in New York. Of course, our most famous food item is deep-dish pizza. Most food websites put Lou Malnati’s as the top place to try this, but Giordano’s and Connie’s are also good places to go. For those looking to avoid atherosclerosis, there are a myriad of options for thinner crust pizza (including the three aforementioned places). In particular, Home Run Inn is a Chicago-bred pizza chain known for their thin-ish, flaky crust, almost like puff pastry. They have nine locations, and they sell some of the best frozen premade pizza I’ve ever eaten in every grocery store in the area. 

The Chicago hot dog, a 100% beef hot dog with basically everything but ketchup, is another well-known food item, and Portillo’s is the most iconic place to get one. There are many other shops all over Chicago that put their own spin on this classic.

In looking up other Chicago food for this, there were things I found out that I’m excited to try. Puerto Ricans brought over the jibarito, which is basically a torta that uses fried plantains instead of bread. A restaurant called Avec makes medjool dates stuffed with chorizo. There’s mac and cheese grilled cheeses, rainbow ice cream cones, T-bone steaks, tacos in bags and donut ice cream sandwiches. Chicagoans are not afraid to take risks with their food and mash things up to make incredible combinations.


Home Run Inn Pizza; Portillo’s hot dogs; a jibarito. None of these photos are mine.

The relatively easy navigability

Unlike many US major cities (including the one I live in now), Chicago has a comprehensive, relatively clean, and relatively cheap public transport system that takes you all over the city as well as to several suburbs. As far as US cities go, only New York, Boston and Washington, D.C. are comparable in terms of accessibility by public transport. A car does become necessary as you venture farther out into suburbia, but in the city, you probably don’t need a car.

Also unlike in many US major cities, Chicago’s streets are arranged in a grid. This basically means that every street is either parallel or perpendicular to every other street, and it makes navigation substantially easier. You will not find any five-way intersections, randomly placed roundabouts, or streets in the arrangement of a four-year-old kid’s best drawing like you would in Boston or London. It is substantially easier to drive in Chicago than in Boston, New York, or LA. (That said, it is a major city—there is plenty of traffic, and people will honk and be mean. But driving culture is not nearly as cutthroat as in LA or Boston.)

I realize that navigability is a bit of a weird thing to highlight in a travel post about Chicago, but I find it to be really important! I thank God for Chicago’s navigability every time I’m back!

I could go on, but I don’t want to make this post too long. In short, Chicago is amazing, and I would recommend it to everyone I know! 

Simi Akintorin