When I mention “ Chicago” to other people, I’m often met with a mixed bag of reviews.
Some folks jump at the chance to remind me it’s a dangerous, crime-riddled city.
Others ask me “What’s even in Chicago?”
And then there’s the classic: “But the winters are SO cold.”
But I love defending Chicago. Because as a local, I think it’s the best major city in America, hands down.
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A Towering Skyline Meets Lake Michigan
I grew up in the South but my family is originally from the Midwest. I spent almost every summer as a child visiting the Great Lakes, specifically Northern Michigan.
I remember telling classmates and teachers where I’d be taking my summer vacation and I was always given a strange look, one that implied, “What could possibly be in Michigan?” But my answer was always simple: Lake Michigan.
Many people don’t realize that Chicago sits directly on Lake Michigan.
They also don’t realize that Lake Michigan isn’t just a lake. It’s an enormous body of water that feels like an ocean. In fact, Lake Michigan is the 5th largest lake in the world [ source]. It has all the benefits of “real beaches,” minus the cons.
This unofficial Lake Michigan motto says it best: “No salt. No sharks. No worries.”
I’d argue that Lake Michigan is one of the top factors as to why Chicago is so great. Not only does the lake add a stunning, striking contrast to Chicago’s towering skyline, but I think it brings the city down to earth. Lake Michigan breaks up the concrete jungle with its vastness. It reminds you to take a deep breath amidst the city noise.
Midwestern Hospitality
I’ll never forget the first time I visited New York City. After that trip, I came home to North Carolina and was relieved to be met by that sweet ole’ Southern hospitality as soon as my plane touched down. It was an experience that stuck with me.
The first time I came to Chicago, I didn’t feel that jarring contrast. Instead, I felt right at home. The people were friendly — making small talk at grocery checkouts and complimenting strangers on the street.
Now, being a local, I still feel this.
The coffee shop around the corner knows my name and order.
I’ve gotten farmer’s market freebies after having conversations with local vendors.
Just the other day I passed by a film set on my way home from the grocery store. Instead of being yelled at to get out of the way, a crew member politely stopped me. They asked where I was headed and let me walk down my sidewalk, even though it was where they were filming.
These might seem like small things — anecdotal pieces that show off Chicago’s sense of community, but the small things add up.
I think a big part of Chicago’s charm lies in the fact that it lacks the lore and fanfare synonymous with places like New York City and LA.
Of course, Chicago has a rich, storied history, but it feels like all of that history and legend didn’t go to Chicagoans’ heads. Chicago still feels real. Chicago still feels like a people’s city.
A City Built for People
I can’t tell you how many visiting friends have walked the Chicago Riverwalk with me and expressed that they wished their cities had something similar.
Those same friends have pointed out how cool it is that Chicago has accessible public beaches like North Avenue Beach and scenic urban trails like the Lakefront Trail. I have to agree with them.
When I look around, I see a city and urban design that was planned with people in mind. Places where people can gather to eat, socialize, play, and just be part of the city outside of their homes and places of work.
Spaces like these are known as “third places” and they play a huge role in your overall mental health and wellbeing [ source]. In downtown Chicago alone, you have the Riverwalk, Grant Park,Navy Pier, and part of the Lakefront Trail. On the other hand, there are tons of indoor spaces like coffee shops and cultural centers where people can come together.
Not to mention, Chicago’s housing — while expensive — is cheaper than housing in New York City and LA. [ Source]
I get that other cities have similar amenities, but my point is that Chicago has all of these things. This compilation of good urban design, accessible third places, and decent housing options all play a role in making Chicago feel truly livable.
Chicago Has Something for Everyone
Theoretically, I could go to the beach, catch a Cubs game, ride a Ferris wheel, visit the zoo, dine at a top restaurant, and attend a play or performance in one day in Chicago.
It would be a packed day for sure, but the point is that I could do it all if I really wanted to.
The common draw of most cities is that they offer residents and visitors an abundance of things to do within a compact area.
Chicago is no exception.
Residents of other cities might come at me claiming that their cities offer similar amenities, activities, and attractions as Chicago. However, the sheer diversity of things to do is what sets Chicago apart.
Chicago is a city for sports fans, arts and culture lovers, foodies, and outdoor enthusiasts alike. Throw in any other category of interest and I’m sure Chicago has activities for that, too.
As a resident, it feels like something is going on every day of the week, all year long, across the city. There are activities to partake in, winter or summer, rain or shine. I’ve never once thought to myself, “I’m bored here.”
The abundance and diversity of things to do make Chicago exciting and dynamic. One day I could decide to lean into my outdoorsy side by kayaking the Chicago River and then escape to a state or national park only a day trip away.
The next day I could indulge in city life by visiting the Art Institute and shopping in the Loop. Another day, I could pretend to be in a small town by exploring neighborhoods like Roscoe Village or Andersonville, which are full of local charm.
There’s no limit to the things you can do and experiences you can have in Chicago.
A City Where You Can Walk, Drive, Bike, and Take Public Transit
Can you name a major city in America that is genuinely walkable, driveable, bikeable, and has good public transportation?
It’s tricky, isn’t it?
I’ll tell you: Chicago.
Most cities boast one or two strong transportation methods. For example, New York City has an awesome subway system and walking is one of the best ways to get around. But driving in New York would be a nightmare. Cities like LA are driving cities, but traffic is bad and walking can be tricky. [ source]
In Chicago, you have a good range of options for getting around. I can easily hop on the “L” to go downtown into the Loop. I can take buses if I don’t want to take the train. I can walk or even bike across several Chicago neighborhoods if I want to. On the other hand, I can easily drive to get groceries and run errands.
The fact that at the very least, Chicago has the infrastructure for different types of transportation, makes it easy to rank highly in this category. [ source] [ source]
Summers Make the Winters Worth It
Outsiders love to harp on Chicago’s cold winters.
But I’ll tell you what any Chicago local knows to be true: the summers make the winters worth it.
Yes, it’s true that our winters can be cold, long, dreary, and frankly, depressing. But our summers are unbeatable. The city may get hot, but we have cool, refreshing Lake Michigan beaches at our fingertips.
I get that Los Angeles and Miami are situated on beaches but Chicago beaches don’t have the salt or sharks to worry about. Our beaches also tend to be less crowded than those of coastal American cities.
The summer buzz may get old for some people, but locals savor it because we appreciate good weather days after long stretches of bad ones. So many cities have this summer feeling of exhaustion, while Chicago’s summer feeling is one of exhilaration. Everyone wants to be outside, and there’s a buzz in the air that can’t be extinguished.
I’ve always said I wanted to live in a place that makes me feel like I don’t want to escape it, and Chicago summers are the embodiment of this. This time of year in Chicago feels like a vacation where you want to soak up every minute.
In Conclusion …
Living in Chicago truly feels like taking advantage of an open secret. Anyone who lives here knows how special a place it is, but it’s often overlooked by people who have never visited. My advice is to not be so quick to judge the Windy City. Chances are, one visit will change your mind.
It’s like the lyrics say in the song, “End of Beginning” by Joe Keery, “And when I’m back in Chicago, I feel it.”
