Chicago isn't what the headlines say. Honestly, if you only watched the nightly news or scrolled through clickbait Twitter threads, you’d think the city was a literal war zone or some kind of decaying industrial relic. It’s not. It’s a massive, vibrating, architectural marvel that somehow keeps its Midwestern politeness while operating with the intensity of a global financial hub. You’ve probably heard people call it the "Second City," a nickname that actually traces back to the Great Chicago Fire of 1871, but today, that name feels a bit like an insult to a place that often leads the nation in manufacturing, tech, and—no joke—the best food scene in the country.
People come for the Bean. They stay because they realized they spent three hours in the Art Institute and forgot to eat.
The Deep Dish Myth and What Locals Actually Eat
Let’s get this out of the way immediately: Chicagoans do not eat deep dish pizza every Tuesday. We just don't. Deep dish is an event. It’s a heavy, buttery, structural engineering project that Lou Malnati’s and Giordano’s have turned into an art form, but for the average person living in Logan Square or Bridgeport, deep dish is for when your cousins from Iowa come to visit.
📖 Related: What Is The Time Difference Between New York and Other Major Cities? A Real-World Guide
If you want to eat like a local, you’re looking for "tavern style."
It’s thin. It’s crispy. It’s cut into squares. Why squares? Because back in the day, tavern owners in neighborhoods like Beverly or Cicero wanted to give patrons a little something salty to keep them drinking, and a square fits on a napkin better than a floppy triangle does. This is the real Chicago pizza. When you’re at Vito & Nick’s on the South Side, you aren't seeing tourists; you’re seeing families who have been ordering the same sausage thin-crust for forty years.
Then there’s the Italian Beef. Thanks to the show The Bear, everyone and their mother now knows about the "dipped" sandwich. But here is the nuance people miss: the beef is a communal experience. You go to Al’s #1 Italian Beef on Taylor Street, and you see the "Chicago Lean." You have to lean over the counter so the gravy doesn't ruin your shoes. It’s a messy, glorious ritual. And don’t even think about asking for ketchup on a hot dog. Gene & Jude’s in River Grove doesn't even have it in the building. They will literally point to the door.
The Segregation Reality No One Likes to Talk About
We have to be real for a second. Chicago is a city of neighborhoods—77 of them, officially—but it’s also one of the most segregated cities in America. This isn't just an "opinion"; it’s baked into the geography. The "L" lines, specifically the Red Line, tell a story of two different worlds. You can take the train from the gleaming glass towers of the Loop up to the leafy, affluent streets of Lincoln Park, and then ride it south into areas that have been systematically disinvested for decades.
Sociologist Mary Pattillo has written extensively about the Black middle class in Chicago and the complexities of neighborhood dynamics here. It’s not just "north is rich, south is poor." That’s a lazy oversimplification. Places like Hyde Park, home to the University of Chicago, are intellectual powerhouses with incredible history, but the city’s history of "redlining" and restrictive covenants created borders that still feel very much alive today.
The lakefront is the great equalizer.
By law, Chicago’s lakefront is "open, clear, and free." This dates back to Aaron Montgomery Ward, the mail-order tycoon who fought tooth and nail to keep the lakefront from being filled with buildings. Because of him, we have 26 miles of public beaches and trails. Whether you live in a multi-million dollar condo in the Gold Coast or a small apartment in Rogers Park, the lake belongs to you. It is the city’s front yard, and in the summer, it’s the only place where the entire city actually mixes.
Winter is a Personality Trait
You haven't lived until you’ve experienced "The Hawk." That’s what locals call the wind that whips off Lake Michigan in January. It doesn’t just blow; it bites. It finds the one gap in your scarf and makes you question every life choice that led you to 41 degrees north latitude.
But there is a strange, shared trauma that makes Chicagoans incredibly nice.
When your car is buried under three feet of snow after a blizzard, your neighbor—the one you haven't spoken to since October—will be out there with a shovel helping you dig out. We call it "Dibs." It’s a controversial, unofficial law: if you shovel out a parking spot on a public street, it’s yours. People mark their "territory" with lawn chairs, broken ironing boards, or old crates. It’s chaotic. It’s technically illegal. But if you move someone’s Dibs chair? You’re asking for a flat tire or a very sternly worded note on your windshield.
👉 See also: Finding the Peak: Why the US Map Fall Foliage Never Quite Looks the Same Twice
The Architecture is Actually the Main Character
Most people think of New York when they think of skyscrapers, but Chicago is where the skyscraper was born. After the Great Fire, the city became a blank canvas. Architects like Louis Sullivan and Daniel Burnham didn't just want to build tall; they wanted to build beautiful.
If you do one "touristy" thing, it has to be the Chicago Architecture Center’s river cruise. It sounds cliché. It’s not. Standing on a boat looking up at the Willis Tower (locals still call it the Sears Tower, and we will never stop) while floating past the neo-Gothic Tribune Tower and the honeycomb-shaped Marina City is a religious experience for anyone who likes design. You see the transition from heavy masonry to the "International Style" of Mies van der Rohe, who famously said "less is more."
Then you have the 16th Street murals in Pilsen. That’s architecture too, just a different kind. Pilsen is the heart of the Mexican-American community, and the walls there tell stories of revolution, family, and survival. It’s a living museum.
The Economy is More Than Just "Old Industry"
Chicago used to be the "Hog Butcher for the World," as Carl Sandburg put it. We processed the meat, we built the steel, we moved the freight. While some of that is still true—Chicago remains the rail hub of North America—the economy has pivoted hard.
Google has a massive presence in the West Loop (the old meatpacking district, naturally). Salesforce just finished a massive tower. The city has become a hub for logistics tech and "fintech" because of the Chicago Mercantile Exchange. People forget that the world's prices for wheat, corn, and belly fat are basically set at the corner of LaSalle and Jackson.
The "brain drain" from the Midwest usually ends in Chicago. Kids graduate from the University of Michigan, UIUC, or Wisconsin-Madison and they don't all go to San Francisco anymore. They come here because you can actually afford an apartment and still have a career in high-frequency trading or biomedical research.
Why the "Second City" Label is Wrong
The term "Second City" actually came from a 1952 book by A.J. Liebling, a New Yorker who spent a year here and hated it. He called it a "second-rate" New York. We took that insult and turned it into a badge of honor. We named our most famous comedy theater after it—the place where Bill Murray, Tina Fey, and Steve Carell got their start.
Chicago doesn't want to be New York.
It’s too clean for that. Seriously, the alley system in Chicago means there isn't trash piled on the sidewalks like in Manhattan. It’s a small detail, but it changes the whole vibe of the city. It’s a "big" city that feels like a collection of small towns. You go to a dive bar like The Old Town Ale House and you’ll find a billionaire sitting next to a guy who fixes elevators, both of them arguing about whether the Bears should have traded Justin Fields.
Actionable Tips for Navigating the City Like a Pro
If you’re actually planning to head to Chicago, don't just stay in the Loop. The Loop is for work and museums. The life of the city is in the neighborhoods.
- Skip the Navy Pier Ferris Wheel: Unless you have kids who are screaming for it, Navy Pier is a tourist trap. Instead, go to the 95th floor of the Hancock Building (now called 875 North Michigan Avenue) for a drink. The view is better and you don't have to pay for an observation deck ticket if you're buying a cocktail.
- The "L" is your best friend: Buy a Ventra card. The Blue Line takes you from O’Hare straight to the city for five bucks. Taking an Uber from the airport during rush hour is a soul-crushing ninety-minute mistake that will cost you $80.
- Museum Free Days: If you’re a flat-out local or have a friend who is, check the schedule for the Field Museum or the Shedd Aquarium. They have specific days where Illinois residents get in free.
- Check out the "606": It’s an elevated rail line converted into a walking and biking trail, similar to the High Line in NYC but way less crowded and more focused on actual neighborhood commuting. It connects Wicker Park, Bucktown, and Humboldt Park.
- The Jazz Scene is Real: Skip the "Top 10" lists and go to the Green Mill in Uptown. It’s an old Al Capone hangout, the booths are original, and the music is world-class. They have a "quiet" rule—if you talk during the set, the regulars will shush you. Respect it.
Chicago is a city that requires a bit of grit. It’s loud, it’s cold for five months of the year, and the politics are... complicated, to put it mildly. But there is a soul here that you don't find in the hyper-polished coastal cities. It’s a place that builds things, eats well, and doesn't care if you like it or not. That’s probably why we like it so much.