Chicago

Chicago is a city of neighborhoods — 77 officially mapped since the 1920s — and locals identify hard with their corner of the grid. This is not one homogenous place. It's South Siders vs. North Siders, Cubs fans vs. White Sox fans, deep-dish loyalists vs. people who will argue thin-crust is more authentically Chicago. All of it is real and none of it is performance.

Put ketchup on a Chicago-style hot dog and watch people physically recoil. The dog comes dragged through the garden (mustard, onions, relish, tomato, pickle, peppers, celery salt), and that's not negotiable. Italian beef, ordered "dipped" so the bun soaks through with the braising liquid, is a different religion entirely. Ask for giardiniera on top.

Chicago is the birthplace of improv comedy. Second City and iO Theater produced Tina Fey, Amy Poehler, Bill Murray, Steve Carell — the list goes on. Catching a show at one of these theaters is genuinely great, not tourist-trap great. Drill music originated here too, a fact the city has a complicated relationship with. And the Chicago blues scene is completely legitimate — the Blues Festival in June is the largest free blues festival in the world.

Here's the thing about locals: they're Midwestern-friendly but not precious about it. They'll give you directions, recommend their favorite beef stand, complain about the weather in the same breath. The 'L' rattling overhead is background noise. The lake is just "the lake." And everyone has been complaining about the same potholes since 2009.

No ketchup. Ever. On a Chicago-style hot dog.

This is the one rule locals enforce without irony.. Order your Italian beef 'dipped' — the bun goes into the braising liquid. Ask for giardiniera (hot peppers) to make it a proper Chicago beef..

Pluralize store names: it's 'the Jewels' (Jewel-Osco grocery), 'Targets,' 'Aldi's.' Makes no grammatical sense. Do it anyway..

After a snowstorm, locals shovel out their street parking spot and claim it with lawn chairs, cones, or random furniture. This is called 'dibs' and is a deeply serious institution.. The Chicago Handshake is a boilermaker: a can or pint of Old Style beer plus a shot of Malört (a wormwood liquor that tastes like grapefruit rind and regret).

Order one at a dive bar. The bartender will respect you.. Everything is '20 minutes away.

' It doesn't matter if it's three blocks or across the city during rush hour. Chicagoans will tell you '20 minutes.' Plan accordingly..

Call it 'the L' or 'the El' — never 'the subway.' It's mostly elevated, not underground. Correct anyone who calls it a subway with extreme confidence..

Expressways go by names, not numbers. I-55 is 'the Stevenson.' I-290 is 'the Ike.

' If you're navigating by number, you'll confuse every local you ask for directions.. Directions use 'inbound' (toward the city center) and 'outbound' (away from it), not compass directions.. 16-inch softball (played without gloves) is a genuine Chicago institution.

Summer nights, lakefront parks, broken fingers worn as badges of honor.

The tourist areas — the Loop, River North, the Magnificent Mile, Wicker Park, Lincoln Park, Lakeview, and the Gold Coast — are as safe as any major American city. Millions of people visit every year and go home without incident. The scary crime statistics you see in headlines are concentrated in specific neighborhoods on the South and West Sides that you simply won't wander into as a tourist. Roughly 90% of violent crime is reported in just a few neighborhoods well outside tourist zones.

That said, stay sharp. Petty theft and pickpocketing happen on Michigan Avenue, at Union Station, and on the L during peak hours. Keep bags zipped and in front of you. Don't flash expensive jewelry or stare at your phone with your arms extended in crowded spots.

Areas to genuinely avoid: Englewood, West and East Garfield Park, Washington Park, South Chicago, North Lawndale, and Roseland. These are far from where tourists spend time, but good to know.

At night: River North, the Theater District along State Street, and Michigan Avenue are all active and well-lit and fine to walk. Use a rideshare late at night rather than walking alone in unfamiliar territory. Don't take shortcuts through alleys.

One more honest note: Chicago's reputation is significantly worse than the reality for visitors. The same media cycle that makes it sound like a war zone overlooks that the Art Institute, Millennium Park, and the lakefront draw tens of millions of visitors without regular incident. Use the same awareness you'd bring to any large American city, and you'll be fine.

The CTA is genuinely excellent and you should use it. Eight color-coded 'L' lines plus 127 bus routes cover the city well. Standard rail and bus fare is $2.50 per ride. Get a Ventra card (reloadable, also works via contactless credit card or phone) — it gives you two free transfers within two hours of starting a trip.

From O'Hare: Blue Line, 24/7, about 45 minutes to the Loop, costs $5. From Midway: Orange Line, 25–30 minutes to the Loop, $2.50. The 7-day pass at $28 covers unlimited CTA rides and makes sense for anyone staying five or more nights. Download the Ventra app to track real-time arrivals and reload your balance.

The Red and Blue Lines run 24/7 — useful for late nights out. Other lines stop running around 1–2am.

Divvy bike share has 950+ stations citywide. Great for short hops between neighborhoods when it's not brutally cold. Chicago has 450+ miles of bike lanes.

For airport rides: rideshares run $35–$55 from O'Hare depending on surge pricing. The L is almost always faster and a fraction of the cost.

Chicago is also very walkable. The grid system makes navigation intuitive. Eight blocks equals one mile. Madison Street runs east-west as the zero line; State Street runs north-south. An address like 3200 N. Clark puts you exactly 32 blocks north of Madison. You'll get your bearings fast. The underground Pedway connects 40+ blocks in the Central Business District — extremely useful in winter.

One heads-up: in March 2026, the CTA sued the federal government over $3.1 billion in frozen transit funding. Service on some lines has been inconsistent. Check the Ventra app for alerts before you ride.