There are certain things about Chicago that apparently only exist in the minds of people who grew up in the suburbs, went away to college, and then moved into the city at 22.

These are people who have lived in Chicago for three years and somehow know more about being a Chicagoan than people who have lived here their entire lives.

They have rules.

And not just rules. Chicago rules.

The kind of rules that, if you don’t follow them, apparently the city will revoke your Chicago card.

Here are a few.

Cubs vs. White Sox

According to the people who have recently moved to the city, Chicago is divided into two warring tribes: Cubs fans on the North Side and White Sox fans on the South Side.

You must pick one.

You cannot possibly root for both.

This is nonsense.

Plenty of Chicagoans root for both teams.

Because here’s the thing: we root for Chicago.

Sure, if the Cubs and White Sox are playing each other, you might have a preference. And yes, we might make fun of North Siders or South Siders depending on where we live and who we’re talking to.

That’s part of the fun.

But when it comes down to it, they’re both Chicago teams.

When one of them is playing somebody from St. Louis, Milwaukee, Detroit, New York or wherever, I’m not suddenly going to pretend they’re the enemy because I have a preferred baseball team.

That’s not how this works.

The idea that Chicagoans are required to hate one of our own teams is something I suspect was invented by somebody who discovered Wrigleyville after graduation and thought neighborhood boundaries were a personality.

Ketchup on a hot dog

This one drives me crazy.

Yes, you can put ketchup on a hot dog in Chicago.

You just don’t put ketchup on a Chicago dog.

Those are two different things.

A Chicago dog is a specific hot dog. It comes with mustard, relish, onion, tomato, sport peppers, celery salt, a pickle and whatever other argument people want to have about the proper arrangement of vegetables.

There is already tomato on it.

Putting ketchup on it would be redundant.

It’s like putting pineapple on a Hawaiian pizza and then announcing that pineapple is forbidden on pizza.

No.

You can put ketchup on a regular hot dog.

You can put mustard on it.

You can put sauerkraut on it.

You can put whatever the hell you want on it.

The only people who seem genuinely offended by this are the gatekeepers.

You know the type.

They’ve lived in Logan Square for fourteen months and now they’re prepared to lecture you about the proper application of condiments.

Relax.

Nobody is coming to take away your Chicago passport because you ordered ketchup.

Malört

And then there’s Malört.

Malört is supposedly this essential part of the Chicago experience.

Except it isn’t.

It wasn’t.

And it certainly wasn’t when I was growing up.

Somehow this stuff has gone from obscure, terrible-tasting liquor to The Official Beverage of Authentic Chicago™.

It isn’t.

It’s a manufactured Chicago tradition that seems to have become popular because people who moved here wanted something they could use to demonstrate that they were really Chicago now.

“Yeah, I’m from Naperville, but I’ve lived in Chicago for six years and I drink Malört.”

Congratulations.

I have bad news for you.

Drinking something that tastes like somebody distilled a tire fire doesn’t make you more Chicago.

And let’s be honest about what happens.

Some bartender gives a group of twenty-something transplants a round of Malört.

Everyone takes a shot.

Everyone makes the same horrible face.

Everyone laughs.

Someone takes a picture.

And suddenly it’s a Chicago tradition.

No.

That’s not a tradition.

That’s a bar trick.

Malört isn’t some sacred Chicago inheritance passed down from generation to generation.

It’s something that became fashionable because people started telling other people that it was fashionable.

You don’t have to drink Malört to be a Chicagoan.

You don’t have to hate the Cubs if you’re a Sox fan.

You don’t have to hate the Sox if you’re a Cubs fan.

And you can put ketchup on your damn hot dog.

You just can’t put it on a Chicago dog and then call it a Chicago dog.

There.

Now you can go back to Naperville.

Whenever I buy a pass, I immediately start doing the math. I need to know if I’m getting my money’s worth.

Gym membership? I mentally keep track of how many times I go and calculate the cost per visit. Ski pass? Same thing. I want to know exactly what each day of skiing cost me. There’s something deeply satisfying about watching that number drop. It turns recreation into a very boring accounting exercise, which apparently is how I like to have fun now.

This week I added a new one: Divvy.

Divvy is Chicago’s bike-share program. I bought an annual membership, which gives me 45-minute rides on regular bikes for free, plus reduced rates on e-bikes and scooters.

There was a promotion, so my one-year membership cost $99.

And the clock immediately started.

On Monday, I took a regular Divvy bike to an activity and rode one home. Two rides.

Cost per ride: $49.50.

Not great. But this is a long game.

The next day, I went to the gym and took a Divvy scooter home. That ride cost me an additional $1.56, bringing my total Divvy investment to $100.56.

However – and this is the important part -I now had three rides.

Cost per ride: $33.52.

Look at that. In 24 hours, I had slashed my transportation costs by almost a third.

Of course, I couldn’t leave it there. I calculated the minutes, too.

So far, I’ve used Divvy for 51 minutes, which puts me at approximately $1.97 per minute.

Again, terrible.

If someone offered me transportation for $118 an hour, I would probably decline.

But I’ve had the membership for less than a week. These are merely the startup costs. Every time I climb onto one of those free regular bikes, the number drops a little more.

And now I have a goal.

Not to exercise more. Not to reduce my carbon footprint. Not to explore Chicago by bike. Those would all be reasonable goals. No. I want to drive that cost-per-ride number into the ground. I want to reach the point where every Divvy ride costs me pennies. I want Divvy executives looking at my account and wondering if perhaps they made a terrible mistake.

So I’ll keep track and post an update here every now and then.

Current standings:

Total spent: $100.56
Total rides: 3
Cost per ride: $33.52
Total riding time: 51 minutes
Cost per minute: $1.97

Those numbers are going down. This may eventually become the cheapest transportation I’ve ever had. Or I may spend $99 on a bike membership and lose interest by October.

That’s why we track the dollars.

From AI:

Chicago’s Leavitt Street is named after David Leavitt, a New York banker and financier who played an important role in saving the construction of the Illinois and Michigan Canal.

In the 1840s, the canal project was running out of money and in danger of collapsing. Leavitt, who represented bondholders and helped arrange financing to complete the canal, was instrumental in keeping the project alive. The canal’s completion in 1848 transformed Chicago into a major transportation and commercial hub by linking the Great Lakes to the Mississippi River system. In gratitude for his efforts, Chicago named Leavitt Street after him.

It’s one of many Chicago streets named after people who helped build the city, even though David Leavitt himself was a New Yorker and not a Chicago resident.

I’ll do this from time to time, but AI makes it so much easier now.  I think most people (including myself) drive down roads all day long without any thought to who they are named for.

When I parked my car (on the street) last night after work, my keys were in my workout bag.  Rather than get them out to lock the car, I thought, “What are the odds that something will happen if I leave it unlocked one night?”

Pretty high, apparently.  You wouldn’t think I’d be the guy who underestimates how shitty Chicago is.

When I got in the car this morning, it had been ransacked.  Joke’s on them, I don’t have anything of value, and certainly not in my car.  They just rifled through the console and glove box.  They didn’t bother taking the napkins or Chick-fil-A sauce packets.

So this leaves me with two thoughts:

1.  It is the craziest of odds that the ONE night I leave my car unlocked is the ONE night someone is going down the block trying doors or;
2.  Someone comes down the block every night trying doors.

TBH, I actually think #2 is more likely in Chicago.

In two years, my wife and I can retire and move out of Illinois.  It’s a dream.  All three of my kids want to live here, so I’ll never be able to leave completely.  If I had my druthers, I would leave and never return.  Alas, I will be born and die here.  Something about Thoreau and most men living lives of quiet desperation.

Ten Things I Actually Like About Chicago

After unloading on Chicago the other day, it feels only fair to admit something: there are things I genuinely like about this city. Quite a few, actually. My frustration comes from caring, not indifference. So in the spirit of balance—and maybe sanity—here are Ten Things I Like About Chicago.

1. The Lakefront

The lakefront really is special. Miles of running and biking paths. Beaches that actually feel like beaches. That moment when the skyline rises behind you on one side and open water stretches forever on the other.

You’ve got pickup soccer games, families grilling, twenty-somethings playing volleyball, people swimming, biking, running, walking dogs. It’s alive in the best way. On a good summer day, Chicago feels like a place you’d choose to be.

2. The Sports Teams

I’m a sports guy, and Chicago delivers there.

The Blackhawks, Bears, and Cubs are all top-tier for me. Even in bad years, they matter. Beyond that, we’ve got two basketball teams, two soccer teams (and yes, I do count women’s soccer), and enough sports culture that you’re never far from a game, a bar argument, or a shared heartbreak.

Sports bind people here in a real way.

3. Diversity (The Real Kind)

Not in the buzzword sense. Just… everybody’s here.

Different cultures, backgrounds, languages, traditions—all living on top of each other. It makes the city richer, louder, messier, and more interesting. Which leads directly to…

4. The Food

This is where Chicago punches way above its weight.

Yes, hot dogs. Yes, deep dish. (Also: tavern-style, which I eat far more often than deep dish.) But the real story is that you can get any cuisine you want—and it’s usually cooked by people who actually know what they’re doing because it’s their food.

Years ago, my younger son asked for Chipotle because he wanted Mexican food. I stopped the car and said, “Uh, we live in Chicago.” Then I took him to L’Patron. Lesson learned. Since then, he’s known what’s up.

5. The People

Not the politicians. Not the loudmouths. The regular people.

Midwest sensible. Friendly. Solid neighbors. People who shovel each other’s sidewalks, chat at the bar, help when something goes wrong. For all my issues with the city itself, I genuinely like the people who live here.

6. Public Transportation

I don’t use it as much as I probably should, but it’s there—and it works.

Trains, buses, bikeshares, scooters—you can actually live here without a car if you want. When I think about moving to Utah, this is one of the trade-offs that gives me pause. Out there, you’re driving. Always.

7. Neighborhoods

Chicago is truly a city of neighborhoods.

Some have higher crime, yes. And unlike New York, our neighborhoods tend to be more ethnic and class-segregated, which is a real flaw. But each neighborhood still has its own identity—its festivals, parks, murals, corner bars, and local spots that feel personal.

You don’t just live in Chicago. You live somewhere.

8. Health Care

This is a big one, especially as I get older.

Chicago has outstanding hospitals, many tied directly to medical schools. Top-tier doctors. Top-tier treatment. When something serious happens, you want to be in a city like this.

9. Four Seasons

This one’s mostly here because my wife insists.

I’ll be honest: winter can go pound sand, and August humidity is a crime against humanity. Somehow it feels colder here than in the Wasatch Mountains, which makes no sense. But fine—we get seasons. Snow, spring, summer, fall. Variety counts for something.

10. Colleges

We’re not Boston, but we hold our own.

Between Northwestern, the University of Chicago, UIC, DePaul, Loyola, IIT, and a bunch of others (no offense to the “lesser” ones), the city stays young. You feel it in places like Wrigleyville or Lincoln Park—energy, movement, people figuring things out.

That matters.

So yes, Chicago frustrates the hell out of me. But it also has moments—real ones—where I get why people love it. Maybe the truth is that Chicago, like most complicated things, is hard to live with and hard to leave.

Some days one side wins.
Some days the other does.

Driving back to Chicago from vacation always triggers me.

You fly down the highway, relaxed, windows cracked, thinking maybe this time will be different. And then you hit the outskirts of the city and – bam – tolls, brake lights, construction barrels, and that familiar sense of doom. The vibe is dead. The spiral begins.

I start seething at the thought that I still have to live here, in a city I actively dislike. Chicagoans (read: my wife and kids) seem to accept this place as “normal,” even though most other cities don’t function like this. So without further ado, here are Ten Things I Hate About You (Chicago Edition).

1. Traffic

According to INRIX’s 2025 Global Traffic Scorecard, Chicago is now the most congested city in the United States, officially surpassing New York. Let me repeat that for those who say, “All big cities are like this.”

No. They are not.

Sitting in traffic for hours every week is not normal. It’s not charming. It’s not “the price you pay.” It’s time stolen from your life. See, wife? The data backs me up.

2. Roads

It’s not just traffic – it’s the surface you’re stuck on. Potholes that could swallow a small sedan. Cracked streets. Stoplights every damn block, timed perfectly so you hit every single red. You can drive two miles in Chicago and feel like you just ran an endurance event.

3. Crime

The mayor can say crime is “down,” but no actual resident believes it. Last week, a co-worker’s son was murdered. I’m going to the service today.

Shootings are background noise here. People lose their minds over a school shooting – and rightly so – but Chicago loses that many people every month and it barely registers. It’s tragic, it’s numbing, and it’s unacceptable.

4. Taxes

Between the city and Cook County, we were already near the top. Thanks to recent changes, we’re sprinting toward number one.

So let’s recap:

• Worst traffic
• Worst taxes
• High crime
• Bad schools

And we stay here… why exactly? It’s not because we’re getting good roads, safe neighborhoods, or stellar education in return. The City Council just passed another budget raising—what else—more taxes.

5. Politicians

Just awful across the board.

The Chicago Teachers Union openly and unapologetically owns the current mayor. Every solution is more money. Every failure is met with demands for – wait for it -more money. CPS functions like a jobs program first and a school system second. Student outcomes are an afterthought.

The rest of the City Council isn’t much better. No reform, no accountability, just endless spending. It’s no mystery why the city is losing population. Smart people leave.

6. The Malört People

You know exactly who I mean.

Suburban kids who move here after college and suddenly think they’re urban pioneers. They can’t wait for their college buddies to visit so they can force them to take a shot of Malört and film the reaction.

Here’s a secret: no one who actually grew up in Chicago drinks Malört. Ever. In the entire history of Malört. It’s a performative personality trait, not a tradition.

7. The Weather Gaslighting

Nine months of cold, gray misery, but everyone insists it’s “not that bad” because we get three nice weeks in June. Summer is hot and humid, winter is brutal, spring is mud, and fall lasts about eleven minutes.  Why live with that?

8. Housing Prices That Make No Sense

Home prices in Chicago are wildly out of sync with what you actually get. You pay a premium usually reserved for safe streets, strong schools, and functional infrastructure… and receive none of the above.

Want to buy? Prepare to overpay for aging housing stock, high property taxes, and neighborhoods you’re constantly told are “up and coming.”

Prefer to rent? Same problem. Rents keep climbing while buildings stay old, parking is a nightmare, and you’re still dealing with crime, traffic, and underperforming schools.

Chicago somehow manages to be expensive without being excellent, which might be its most impressive trick.

9. The High Cost of Everything

It’s not just taxes and housing – it’s everything. Gas costs more. Groceries cost more. Parking costs more. (Dear God, don’t get me started on parking fees) Tolls, fees, “convenience charges,” and random surcharges pile up until you’re bleeding cash without noticing where it all went.

You pay more at every step, every day, just for the privilege of being here. And again, that would be one thing if the city delivered top-tier services in return – but it doesn’t. You’re paying premium prices for a very non-premium experience.

Chicago has somehow mastered the art of making ordinary life more expensive than it needs to be.

10. The Constant Sense of Friction

Nothing in Chicago is easy. Every routine task – commuting, parking, paying a bill, getting a permit, scheduling anything—comes with unnecessary resistance. There’s always a form, a fee, a delay, or some unofficial workaround everyone just accepts.

Life here feels permanently set to hard mode for no apparent reason. You burn an incredible amount of energy just navigating ordinary days. And you don’t fully realize how draining that is until you leave town and feel how much lighter everything suddenly becomes.  I spend a few weeks each year in Utah and it’s NOTHING like Chicago.  No traffic, wide open spaces, no crime where we stay, life is easy.

That contrast is brutal.

I know. There are good restaurants. There’s culture. There are moments when the lake is perfect, and the skyline looks incredible. I get why people love it.

I don’t.

And every time I crawl back into the city, sitting in traffic, paying a toll to enter my own misery, I’m reminded that accepting something as usual doesn’t make it normal.

It just makes you stuck.