A Local’s Guide to What Chicago Is Really Known For

If you ask an outsider what Chicago, Illinois, is known for, they’ll probably focus on the big three: deep-dish pizza, wind, and gun violence.

If you ask a local like me, you might still get some overlap, but things also get a heck of a lot more nuanced. 

Chicago is known for its food scene, its architecture, its placement on Lake Michigan, and for being a city of distinct neighborhoods. That’s the positive spin. It’s also known for its horrible weather, traffic, gun violence, and high cost of living. 

Everything I’ll say here comes from a place of love because I truly believe Chicago is one of the best cities in the world. If we’re talking food, I’d argue that it’s the most delicious city in the United States at the very least. 

I’m likely biased on that last statement, but I’ve been to every state in the country sampling the local eats and I said what I said.

Why don’t we start there?

The Pizza

If you’re a Chicago newbie or just passing through, you likely connect Chicago to deep-dish pizza. That’s the really thick stuff that people from New York City like to make fun of because it’s an easy mark.

It sits in your belly like a lead balloon and that’s the G-rated version.

Yes, locals eat deep-dish pizza. That said, it’s a rare occurrence. It’s typically a request from visiting family and friends, but it’s not what you’d order if you need a quick slice or pie to-go on a lazy Tuesday night. 

Chicagoans know that some of the best pizza on the planet is found beyond the regular deep-dish spots downtown and around. 

My personal favorite is Pequod’s. They have both a thin-crust pizza and pan-style that I think of fondly enough that I’ve written a love letter to it. 

Real Chicago-style pizza, though, is tavern-style. This is a square, thin-crust pizza with toppings like giardiniera, sausage, and peppers.

If you don’t have one of these within a few blocks you’re probably living in the wrong neighborhood. Growing up, mine was Di Vita’s Restaurant. If you try to fold this stuff, you’ll also be shamed right out of the neighborhood.

Hot Dogs and Italian Beef

Many food items in Chicago will give you heartburn, but the Italian beef sandwich likely tops the list right after that deep-dish pizza you just housed. 

Honestly, it’s not my thing. I don’t eat a ton of red meat anymore, but I’d usually rather have a burger if that’s what I’m after. (Some of the best burgers in Chicago are at Small Cheval, by the way. In-N-Out, it’s just not a contest.)

If you can’t see yourself leaving the Windy City without noshing on some beef, Mr. Beef on Orleans is getting the most attention lately. That’s the one featured in The Bear. Al’s #1 Italian Beef is another favorite with locations all over the city.

For the best Chicago-style hot dogs, you’ll need to head out to the ‘burbs. You’ll be rewarded with the creepy blinking eyes of hot dogs dressed as Tarzan and Jane on the roof of Superdawg Drive-In in Niles.

I can’t tell you how many hot dogs I’ve consumed from that spot in my lifetime. My dad used to work near there and it’d be a treat when he was in charge of my sustenance. They go down easy is all I’m saying. 

Just keep the ketchup out of it unless you’re talking about the fries. While we’re at it, your Chicago dog should come on a steamed poppy seed bun with a dill pickle spear on the side.

The Fine Dining

Famous Chicago food has to include fine dining. Chicago is right up there when it comes to Michelin stars. 

Alinea, considered by many foodies as one of the best restaurants in the world, has three. Famous Chicago restaurants like Moody Tongue, Ever, Smyth, and Oriole all have two. 

We’ve been lucky enough to eat at Alinea, Moody Tongue, and Ever, and would probably agree that Alinea is at the bottom of that list. I’ve never forgiven Grant Achatz for forcing me to forage for mediocre jerky in one of his most popular plates. 

It has to be delicious first, chef.

Outside of Michelin, though, Chicago has a fantastic fancy food scene. The West Loop alone is a who’s who of celebrity chefs and small plate connoisseurs that will show you a good time if you show them the cash. 

The Craft Beer Scene

Chicago’s craft beer scene has exploded over the last decade. I remember taking a free tour of Half Acre Brewing Company when they first came onto the scene with their own spot in 2008. There wasn’t much to Chicago beer back then unless you loved Old Style.

Chicago’s beer today competes with the best of the best. I used to say San Diego breweries were at the top, but the sheer volume of options in Chicago now is impressive.

Jeppson’s Malört

I think the hype on Malört as the most horrific thing you can drink is overblown. I’ve taken shots of it, sipped it, and can truly say I’ve had worse.

Some of my family members make concoctions in their bathtubs, so I’m coming at this with unique alcohol-related experiences under my belt.

That doesn’t make it less of a big deal in Chicago lore. The bitter liqueur is a right of passage for folks new to Chicago. If you really want to impress us, take a shot with a straight face. Then ask for another.

The Great Chicago Fire

The Great Chicago Fire of 1871 was one of the biggest catastrophes in American history, let alone Chicago history. 

The fire started in a barn owned by Patrick and Catherine O’Leary, but the exact cause remains a mystery. You can leave that poor cow alone, OK?

More than 300 people died as a result and thousands of buildings were destroyed. Martial law was initiated to prevent looting as the ashes smoldered, but that didn’t provide much solace for the full third of Chicagoans who were left homeless as a result.

If you want to see one of the few buildings that survived the fire, visit the Chicago Water Tower downtown.

The World’s Columbian Exposition

The World’s Columbian Exposition of 1893, or the Chicago World’s Fair, was held to celebrate the 400th anniversary of Christopher Columbus’s arrival in the Americas.

No matter how you feel about all of that, you can’t deny the fact that the event had a profound effect on the city’s image as a showcase for the arts, sciences, and architecture. This was the debut of the Ferris wheel.

Chicago also beat out Washington, D.C., and New York City for hosting rights, so that’s cool.

In true Chicago fashion, the fair ended with the assassination of then-mayor Carter Harrison, Sr. You cannot make this shit up.

Chicago Architecture

Chicago’s architecture boasts a rich history that has shaped not only its iconic skyline but also the skylines of big metro areas all over the country. The city pioneered a style known as the Chicago School, at that time known as the Commercial Style. 

The city’s desire to go vertical is obvious as soon as you head downtown, and the best example of that is the Willis Tower, once known as the Sears Tower.

The nearby John Hancock Center, now renamed 875 North Michigan Avenue, boasts some of the city’s best views.

Chicago architecture isn’t just known for its skyscrapers, though. Frank Lloyd Wright and his Prairie style have a big presence here. The Garfield Park Conservatory and its impressive dome are yet another example of unique Chicago building styles.

The Chicago Cultural Center is famous for its interior, a stained glass dome that is close to the top of locals’ favorite spots around the city.

My favorite Chicago vibes are in its residential buildings. 

Two-flat and larger multi-flat brick buildings are still the norm in a good chunk of Chicago’s housing stock. I even grew up in one of these, complete with radiator heating.

Chicago Diversity

Segregation is a real problem in Chicago, but I will always stand by the idea that the city’s diversity is its strength.

My family arrived in Chicago because there was already a thriving Polish community here. You’ll find similar stories for immigrant pockets across Chicago that have become safe spaces for diverse groups of people.

It makes sense when you consider how Chicago came to be.

Jean Baptiste Point du Sable was a Haitian-French trader credited as the founder of Chicago in the late 18th century. As the city’s first non-Indigenous settler, he established a successful trading post near the Chicago River.

This led to commerce with Native Americans and European traders, laying the foundation for modern Chicago’s development.

This is a city that is deeply tied to immigrants as part of its identity.

Chicago Politics

Chicago politics are known for power and corruption. There’s no shortage of stories where wealth, nepotism, and influence are more important than grit and good ideas.

The Daley family alone ran things in the city for a combined 43 years. That’s totally normal, right?

Note: If you want to impress a native Chicagoan, make reference to the real origins of its nickname, The Windy City. Some people think it’s because the city is just that windy — most small towns in Texas are a lot more windy, by the way — but the name’s origins are actually linked to a rivalry with Cincinnati from the 1870s.

Some of that machine-style politics has gone by the wayside in modern times as progressive candidates try to reshape the more old-school Democratic Party in the city. This is definitely an area that deserves criticism.

The Gangsters

Chicago’s history with gangsters is steeped in infamy. Much of that history is centered around the Prohibition era starting in the 1920s. The city’s location made it a hub for illegal activity like bootlegging and speakeasies for people seeking a good score.

Fun fact: Chicago today remains a hub for some of the best speakeasies in the country. They’re all legal, but you still may need a password to gain entry.

Al Capone is probably the city’s biggest name related to gangster activity. Things came to a head after the Saint Valentine’s Day Massacre in 1929 which resulted in the murder of seven members of the city’s North Side Gang.

Two of the assailants were dressed as police officers, but it’s widely believed that it was a hit ordered by Capone.

The history may be grisly, but leave it up to Chicago to monetize it. Chicago gangster tours are one of the most popular tourist attractions for visitors to the city. We’ve been on the Untouchable Tour years ago and had a great time.

Check it out below as the “original” gangster tour plus a few more highly-rated options:

The Obamas

This is more of a modern history, but it’s become a stronger one over the years. Former President Barack Obama began his career as a community organizer in Chicago. Michelle Obama was born and raised in the city. 

Since leaving the presidency, the Obamas still spend most of their time in Washington, D.C., but they’ve retained their property in Hyde Park. That’s a neighborhood on the city’s South Side that is home to the prestigious University of Chicago.

The connection remains if they want to make a more permanent return to Chicago at any point. 

Chicago Sports

Chicago sports are a big deal in the city and you’ll find fans at games where the local teams are doing well or not. It gives us more to complain about when they inevitably disappoint us.

The city also has much to be proud of when it comes to its sports scene. We have two Major League Baseball teams that have won World Series in my lifetime. 

Note: That’s the Chicago White Sox and the Chicago Cubs, those loveable Wrigley Field guys who were able to persevere despite the Curse of the Billy Goat.

If you love hoops, United Center games to watch the Chicago Bulls are very fun. I grew up watching games with my dad during the Michael Jordan era, so I’m spoiled in that regard. We also have a decent WNBA team in the Chicago Sky.

I’m not done yet. The Chicago Bears, our NFL team, usually leave something to be desired, but I’ve seen them play in a Super Bowl. The Chicago Blackhawks, our NHL team, won a Stanley Cup while I sat in a box above during Brian’s insurance days. 

I’m not that fancy, I swear. Corporate America just loves to schmooze. 

I haven’t even gotten into the soccer scene. Chicago sports has it all.

Chicago Comedy

The Chicago comedy scene is huge, and it’s made far-reaching contributions to the comedy world for decades.

I was lucky enough to participate in the 50th anniversary at The Second City, perhaps the city’s best-known comedy venue. They’ve since passed another decade.

That’s just one venue, though. The Lincoln Lodge, Laugh Factory, and Zanies are all fantastic places for a laugh among so many others. This city is hilarious, and the proof is in the big names who have passed through the scene. 

Jim Belushi, John Belushi, Andy Richter, Jane Lynch, John C. Reilly, and Hannibal Buress are all from Chicago or the Chicagoland area. (I’m counting suburbanites here because they tend to do the same for themselves.) 

Fun fact: Hannibal Buress had my phone number for a while. Nothing ever materialized, but I’ll tell anyone who will listen about what could have been. Brian, I kid. I love my life.

Famous Chicagoans

There’s a long list of famous people from Chicago beyond popular comedians. Here’s a taste:

• Gillian Anderson
• Cindy Crawford
• Anna Chlumsky
• John Cusack
• Walt Disney
• Harrison Ford
• Hugh Hefner
• Jennifer Hudson
• Bill Murray
• Robin Williams

The Music Scene

Chicago is a hub for live music. All of the major artists come through here, but it’s also a great city for up-and-coming talent. In the summer months, the city does it up with events like the Grant Park Music Festival and Lollapalooza.

The city also boasts some historical heft in terms of its musical roots. 

Chicago has been an influential force in the overall music landscape across the country. Legends like Nat King Cole and Muddy Waters have roots in Chicago. The city is credited with creating forms of the blues, house music, and Chicago-style jazz.

This is largely thanks to the migration of Black people from the South to cities like Chicago in the first chunk of the 20th century. I’m grateful for it.

Rosa’s Lounge, the Green Mill, and the Sleeping Village in my childhood neighborhood of Avondale are all great spots for live music in Chicago.

READ MORE: Love a musical city? You’ll want to plan a trip to Memphis.

The “L”

The Chicago “L,” short for “elevated,” is the best representation of the city’s public transportation system.

Yes, there are buses and the Metra that take you out to the ‘burbs, but the “L” is where you cut your teeth when it comes to the Chicago Transit Authority (CTA).

Is it possible that you’ll see someone doing something lewd behind a Chicago Tribune newspaper while aboard? Yes. It’s also possible that you’ll come across the whimsical CTA Holiday Train during the winter holidays, so it’s not all bad.

The “L” is iconic because it touches almost every community in the city. People rely on it to go to work, to play, and everything in between. It’s always been a fixture during my time in Chicago.

The Magnificent Mile

The Magnificent Mile is usually on Chicago itineraries for first-time visitors. The stretch of Michigan Avenue is known for its upscale shopping and luxe retail stories, but it’s also a great stroll to check out Chicago architecture and public art.

Don’t miss The Blackstone Hotel, a hotel that has hosted numerous U.S. presidents, and the original Billy Goat Tavern. The pub is famous for starting the Curse of the Billy Goat after the original owner wasn’t allowed into Wrigley Field with his pet goat. 

You may not believe me, but stranger things have happened in this city.

For a true Chicago tourist experience, walk to Millennium Park. This is where you’ll find the Cloud Gate sculpture, more commonly known as The Bean. This Chicago bean isn’t really a bean but a reflective shape made for some fantastic Instagram photos.

You won’t offend anyone by calling it The Bean, by the way. Chicagoans do it, too.

The Art Institute of Chicago

The Art Institute of Chicago is one of the most important art museums in the world. It was founded in 1879 as part of the city’s rebirth following that big fire, and since then has grown to hold over 300,000 pieces across time periods.

That puts it up there as one of the largest collections in the world. This is where you can see Georges Seurat’s A Sunday on La Grande Jatte, the artist’s largest and most well-known painting, and American Gothic by Grant Wood.

The latter is arguably the most well-known piece of American art anywhere.

READ MORE: Learn about Grant Wood’s roots in my guide to Cedar Rapids, Iowa.

If you want to visit the museum, buy tickets ahead of time, especially if you’re here in the summer months.

Lake Michigan

If you’ve never seen a frozen lake before, you’ve probably never felt the beginnings of frostbite, either. I’d still argue it’s worth it. It’s a sight to behold, especially if you’ve never seen pancake ice.

Come summer, Chicago is known for its beach days. Granted, sometimes a dip in the water isn’t recommended because of high levels of bacteria, but that’s not the point. The point is, the lake is lovely to look at even when you can’t swim in it.

For the best Lake Michigan views, head to Lincoln Park or the Adler Planetarium. Leave some time to geek out at the planetarium, certainly, but the museum offers some stunning views of the lake from its balcony even if you’re not here for space.

The Chicago River

The Chicago River is a vital waterway in the city that offers efficient transportation, picturesque city views, and St. Paddy’s Day fun when they dye it green every year.

The river is also an example of creative engineering. Before 1885, the Chicago River used to empty into Lake Michigan. This meant sewage-polluted water flowed into the lake, affecting water supplies for Chicagoans who used that water for daily life.

City officials decided to build a canal that reversed the flow of the river and ended residents’ bouts of cholera and whatever else they got from dirty water. The water would then flow inland and eventually connect with the Mississippi River. 

Yep, they sacrificed one water source for another in the change.

Today, the stormwater and sewage that used to get sent right into the river is now treated at water treatment plants before its return. Numerous upgrades have been costly but mostly effective, although the city’s facilities still fail after big enough storms.

You wouldn’t know all this strolling down the Chicago Riverwalk, a route completed in 2016 that allows people to get from the river in the heart of downtown to the lake.

Chicago Neighborhoods

Chicago is best when it’s taken as the sum of its neighborhoods. Favorites like Lincoln Park, River North, and Lakeview are known for shopping and access to the lake. The West Loop, underrated Humboldt Park, and Logan Square are a must for foodies.

Each neighborhood has its own distinct personality and its own vibes. I grew up in Avondale, a once Polish community that is now all kinds of hipster. I’ve lived in Wicker Park, Humboldt Park, and Jefferson Park since.

While it can take some time to travel from one place to another, spending a full day in one part of the city isn’t a bad move, either. There’s more to Chicago than Navy Pier and the Mag Mile.

The Weather

Winter in Chicago is no joke. It also feels never-ending once you’re in the thick of it. I grew up with birthdays that could mean balmy temperatures or snow boots. My birthday is on March 29.

The thing is, summer isn’t always awesome, either. Yes, the food and music festivals are a great time. Summer can also bring tornadoes, severe thunderstorms and flooding, mosquitoes, and chirping cicadas that make outdoor conversation pointless.

It’s a lot. 

Some say it all builds character, but that’s because they’re just really sad about it all deep down. After seven years in San Diego, our brains and bodies are a little broken when it comes to dealing with Chicago weather. That’s why I tend to focus on other things.

The Traffic

Chicago’s traffic is truly awful. I have nothing supportive to say about this one, other than you should take public transportation whenever possible. Over recent years, it tops metro areas as the worst of the worst, and some of that is the city’s doing.

The city has done things like close down key lanes of traffic on one of the major arteries to and from downtown. These kinds of projects take years to complete, and projects rarely remain on schedule.

Chicago is famous for its two major seasons, winter and construction.

The Gun Violence

If the news was to be believed, you’d think the city was at war. Chicago is the poster child for gun violence and all that is wrong with metro areas run by Democrats. 

The thing is, it doesn’t even crack the top 15 when it comes to deadliest cities, and rural counties generally have higher rates of gun violence than urban cities.

How can this be? What about “Chiraq?”

There are more violent areas of the city that suffer from divestment, generational poverty, and a racial and economic divide that isn’t obvious to those passing through. 

The perceptions people have about Chicago aren’t based on real evidence, though. Chicago is a big city with big city problems, but it isn’t the most violent city in America. It’s not even close.

The thing is, the people enjoying the safest they’ve been in a generation are often the most worried about Chicago’s rates of violent crime. These are people on the North Side where crime has been trending down for decades.

They feel less safe, so it must be true.

We don’t talk about supporting the people in neighborhoods like West Garfield Park or North Lawndale who are affected by gun violence daily. That coverage isn’t as relentless. 

It’s also not as easy to get into the nuances of the city’s issues vs. just reporting on the nightly gun violence numbers. We have a lot of work to do in the city, but we have a lot of work to do as Chicagoans, too.

The High Cost of Living

Locals will lament about the cost of living in the city, but Chicago is much less expensive overall than major cities in California and along the East Coast. That information doesn’t help when you’re dropping bank at the grocery store or the gas pump, but facts are facts.

That all said, Chicago isn’t a cheap place to live. If you want to live close to the lake, I hope you come from new or old money. Dining out can be expensive.

Expect nicer eateries to include a 20% gratuity on your bill, by the way. I support that, but it’s good to know if you’re cheap. (As the daughter of a career server, tip servers appropriately, please.)

The cost of visiting Chicago varies widely, too. Hotels downtown are obviously more expensive than anywhere else, and summertime rates are higher than at any other time. 

The winter holidays can be a pricey time to visit, too. Despite the weather, Chicago does it up with the Christmas lights, markets, and festivals.

Plan ahead if you’re able and you’ll be rewarded with cheaper Chicago travel.

What are Chicagoans known for?

Chicagoans are known for being rabid sports fans, having fierce loyalty to the city, and that Chicago accent. 

I don’t hear it in myself or my friends, by the way. Chicago Fire has it pretty exaggerated.

Chicagoans are also known for having a chip on their shoulder. It’s thanks to years of flyover country comments and musings about violence in the city. I’d argue that it’s warranted by a Chicago population that’s honestly just sick of the discourse. 

I get pretty defensive myself when people suggest Chicago isn’t worth your time, especially when they haven’t been here themselves. People need to get off social media and experience the world a little bit more.

There is so much that’s special about Chicago. The food scene is the best in the country, the architecture is impressive, and there’s enough here to occupy you no matter what kind of weather the city throws at you.

As cheesy as it sounds, though, the people are what make Chicago the most special. We want to make the city better and invest in making that happen.

Planning more travel in the Midwest? Check out these guides:

• Visit North Dakota & Teddy Roosevelt National Park
• Explore Cave Point County Park from the Water
• What’s the Best Way to See the Apostle Islands?
• The Field of Dreams isn’t Just a Movie!
• A Wisconsin Guide for New Glarus Beer

I’m not done yet! Here are a few more guides for the Midwest:

• Check Out Fossils at the Devonian Fossil Gorge
• A Guide to Visits to Iowa City, Iowa
• You Should Spend a Weekend in Door County
• How to Plan Your Trip to Fargo, North Dakota
• A Guide to the Incredible Devils Tower

Want to see more?