Disclosure: I may earn affiliate revenue or commissions if you purchase products from links on my website. The prospect of compensation does not influence what I write about or how my posts are structured. The vast majority of articles on my website do not contain any affiliate links.

It was January 2015 and I stood atop the Marin Headlands outside San Francisco. It was sixty degrees outside and I had just finished a picturesque climb with my cousin. I wasn’t sure how he had procured the road bicycle I was riding, but the fit was perfect.

Perfect–that Bay Area. I gazed out over the Golden Gate Bridge. A little fog but not too much. A stranger took our picture. I had a helmet on which I later learned isn’t the coolest thing to wear, but I still admire the scene that was captured. At that point, I was so sure of my path forward. Get a job at Google or somewhere, move to San Francisco, and live the life that any undergraduate studying Computer Science dreams about.

My dream never came true. I ended up getting rejected by or never heard back from all of the companies that I applied to in the Bay Area. I accepted an internship in Chicago instead.

I never considered Chicago as a second-tier city for the simple reason that I had never considered it at all. I didn’t know anybody who lived in Chicago. I didn’t know any companies that were based in Chicago. The scene of Chicago painted by the Blues Brothers was gritty and not much to my liking. But it’s where I ended up and, perhaps, going in with absolutely no expectations made all the difference.

I had a blast during my summer internship and my first two years of employment. Now, I’m settled in as a Chicagoan and I’m really proud of what this city can offer.

Proximity is Everything

People who can afford to live in Manhattan will brag about being “close to everything.” Certain neighborhoods in Chicago offer relatively-inexpensive closeness to the things people care most about. To live in a city is not just to work in a city but also to enjoy what it has to offer, and Chicago strikes that balance better than anywhere.

On an intern salary (which was not an extravagant tech salary), I was able to live alone in a studio apartment in downtown Chicago. Specifically, in Lakeshore East. I could walk to work in twenty minutes. There was a grocery store on the other side of the park next to my building that was, at that point in my life, the nicest grocery store I had ever been to. I ran along the Chicago River and Lake Michigan each morning, some days even swimming in the fresh water of the lake. From my front door, it took me five minutes (walking) to get to the river trail.

As an intern in Manhattan, you have no discretion in selecting a neighborhood to live in. Living alone is not a luxury you will have, potentially for the better part of your twenties. The people who say that they are “close to everything” usually live in decent neighborhoods but then have to take a dirty, smelly, crowded subway for thirty minutes to get to work and whenever they want to see their far-flung friends.

In my current location, of which my split of rent is less than I paid for the studio apartment three years ago, I have four grocery stores (two being what I would consider top tier) in walking distance. Work is a fifteen-minute walk. I have to cross one street to get to public transportation. I have the best restaurant scene in the country less than a mile away, and the same river trail I used to run is now just a mile away.

Lack of Homogeneity

As someone who works in tech, I have grown wary about moving to San Francisco or Seattle and, to be blunt, having all my friends be computer nerds. I don’t equate a lack of homogeneity with an abundance of diversity, but I’ve met a wide variety of people in Chicago and things have always been exciting. Sure, when talking about ethnic diversity (which I’m really not fixated on), NYC and Los Angeles are probably more diverse, but Chicago holds its own.

The other massive, understated benefit of the lack of concentration of any particular person or group is that tech companies haven’t come in and driven prices up. Historically, I haven’t been sympathetic to people who decry getting priced out of their apartments by wealthy Googlers. I believe in capitalism. However, you don’t have hundreds (if not thousands) of new grads showing up every year making $100k starting salaries, so prices for goods and services across the board haven’t inflated. I’d like to think of it as a well-kept secret.

Cost of Living

To continue my last point, Chicago is an affordable city. A conservative estimate puts New York City as 50% more expensive than Chicago–mainly due to housing–and San Francisco at 130% more expensive than Chicago. Housing again being a major factor.

I have always found such cost of living comparisons useful. Where many would debate such stats in order to defend their cities or exaggerate their relative hardship, I did a significant amount of research into the cost of living for these two cities when I was recently searching for a new job. I spent two years living in a “luxury” building here in Chicago. The equivalent rent in San Francisco would have me paying roughly 80% more. The equivalent amenities, newness, and more in New York City would have started at 150% more. San Francisco, while more expensive to buy in, had a fairly standardized rental market. New York’s rental market was hard to navigate, and in the end, I realized that it just wouldn’t be feasible to move there and not have a roommate.

For many people, rent or mortgage payments will be their largest monthly expense. I am not embarrassed to admit that my largest expense is grocery shopping and dining out (alcohol excluded, for comparison’s sake). I love cooking and I love eating. 3000 calories per day is a normal amount for me. It is a privilege that my rent is so affordable that I can splurge on food. Being in the midwest, I definitely pay less for goods that are produced in the vicinity, but Whole Foods still feels expensive.

When it comes to going out, eating and drinking, Chicago excels. Even at some of the hippest restaurants in the hippest neighborhoods, mixed drinks cost $14 at most. In neighborhoods that cater more to recent grads, craft cocktails topping out at $10 are common. Fine dining is also affordable compared to NYC. $150 a head for top-flight restaurants is commonplace, whereas in NYC that would be considered bush league. Lunch during the week is pretty reasonable, with some of my favorite sit-down restaurants offering set lunch menus for just $15.

Relatively Recent Major Reclaimations

People often forget that Chicago was a dirty, industrial city for most of its history. Following White Flight (and many, other factors that are beside the point) in the mid-20th century, living in downtown Chicago wasn’t glamorous or, in many areas, feasible. Thanks to the reclamation of old stockyards, railyards, and factories, Chicago can often appear to be the most modern major city in America.

Downtown, some of the most significant parts of the contiguous Grant Park, such as the Bean, were built in the last fifteen years. Some less notable parts were finished as recently as 2015. Just north of Grant Park, there is the Lakeshore East neighborhood, which consists about a dozen buildings all master-planned by the same development company. I lived in this neighborhood when I was an intern. Frankly, living there felt like living in the future.

Further West, the neighborhood of West Loop has transformed from a gritty meatpacking district to one of the hottest neighborhoods in America. The blank canvas provided by surface parking lots and old warehouses has allowed the area to transform with stunning quickness. It is dotted with gorgeous new buildings and countless new developments. A neighborhood this close to the downtown of a major metropolitan area being rebuilt from the ground up is simply unprecedented.


Chicago has the best dining scene in America. I’m barely willing to be objective here. I will, however, drill down and make an even more wild, specific point. The Randolph Street/Fulton Market corridor has the strongest concentration of high-quality dining anywhere in the world. Come at me!

Further, Chicago, located at the heart of the heartland transportation routes, also sports a higher concentration of steakhouses than anywhere else in the world. That claim is actually substantiated. Now, you may be asking, does this mean that Chicago dominates the list of worldwide top steakhouses? Not necessarily. In my experience, restaurants in NYC will go the extra inch just for the sake of doing it because they know that 1. It allows them to charge whatever they want and 2. It will matter when the critics come to critique the steakhouses. It would take a true connoisseur to be able to fairly compare the best three steakhouses in Chicago versus the best three in NYC. If price wasn’t a factor, I would actually give it to NYC. Price being relevant, Chicago wins slightly.

Safety and Cleanliness

Chicago had more murders than–

Chicago has a violent crime problem. This will be labeled as insensitive, but the truth is that it occurs far away from the city center. I feel significantly safer walking around Chicago at night than Manhattan, Philadelphia, or San Francisco. Police have a really hard job to do, but the areas in which the majority of Chicagoans work and play are kept incredibly safe.

Not to trivialize the above topic, but Chicago also tends to strike visitors as clean. One major advantage over NYC is that there are alleyways, so you don’t have to walk past piles of garbage on the curb on garbage day. Further, there is no ever-present odor like that which you encounter in summertime NYC or year-round SF. The city feels well-planned and comfortably spaced out, rarely feeling like a concrete jungle.

Summertime Chi

Of course, I want to proclaim Chicago the best city in the world, but the truth is that the winters are miserable. Imagine the coldest cold you’ve ever felt. Now picture that occurring from October to early May. I am from the mountains of Northeastern Pennsylvania, and I rarely felt a wind chill as cold as Chicago’s M-F.

The flip side of the terrible winter is that the city comes alive in the summer. For the summer months, I would rate Chicago among the best cities in the world. It’s beautiful with tons of things to do aside from drinking at overpriced clubs at the tops of high buildings. I never want to leave during the summer and all my friends who come to visit often beg me to let them move in with me. Only partially joking.

Midwestern Attitudes

A major part of what makes the summer in Chicago so fun and what makes living here so different from major cities on the coasts is what I would call the Midwestern Attitude. The central theme is that people are much more friendly and much less obsessed with themselves than they are in the Northeast.

This attitude is usually more subtle than most would suggest, but the truth is that it makes a real difference in helping one maintain a positive outlook on life. From basic daily interactions to dating, this is one of my favorite things about Chicago.


The city’s public transportation is not bad. I use it when I need to, which is quite infrequently. Chicago’s position as a United Airlines hub means a lot of great low-cost flights to popular destinations. Sure, Los Angeles, San Francisco, and NYC all have great flights, too. The one advantage of being located in the middle of the country is that spending a weekend anywhere in the domestic United States is easy. Additionally, Chicago has more direct flights to ski resort airports and major airports near ski resorts than any other city in the world. Maybe the winters aren’t so bad after all.

Why I’ll (Probably) Never Leave Chicago