by Just Another Friendly Occupier

If you ever visit Chicago, don’t you dare come at it like a tourist. Don’t do the plastic skyline boat tours or the overpriced deep-dish temples where they smack your credit card harder than the pizza crust. Don’t shuffle down Navy Pier like you’re trapped in a theme park. Chicago isn’t Disney. Chicago is a living organism made of steel, wind, grit, memory, and a million conversations happening at once.

If you’re going to see it, see it like a native.

Start on the Northwest Side — Foster and Milwaukee — where the air still carries the old neighborhood heartbeat. Walk into King’s 2 like you belong there, because in Chicago you do. Order like someone who’s lived a life:

a double cheeseburger with everything

the biggest fries they’ll shovel into a bag

Greek lemon chicken steaming through the Styrofoam

two gyros overflowing with tzatziki

and the largest cola they’ve got — Pepsi, Coke, whatever’s working that day

Sit down, dig in, talk too loud, laugh too hard. Chicago rewards people who don’t pretend. You give it authenticity, and it gives you a damn good meal and a story.

When you’re full enough to reconsider your choices, head toward the lake. Go to the Adler Planetarium. Sit in the Sky Show like you’re eight years old again and the universe finally wants to explain itself. Chicago has this rare magic where it makes you feel tiny and powerful at the same time — the cosmos above you, the skyline behind you, the lake breathing at your back.

When you step into the lake wind — eyes adjusting, brain still orbiting Jupiter — walk it off. The lakefront path is Chicago’s spinal cord. Follow it down to the Field Museum, that grand stone temple of bones, mummies, and cultures old enough to silence the city’s noise.

Go say hi to Sue.
Stand under the elephants.
Wander until your feet negotiate a ceasefire.

And when you’re ready to leave, travel like a real Chicagoan — no cabs, no half-measures, no tourist shortcuts. Do it the way the city itself moves:

1. Catch the #146 Inner Drive/Michigan Express or #147 Outer Drive Express heading north on Michigan Avenue.
Watch the city breathe: stone giants and glass towers, workers, students, delivery drivers, people fighting winter wind with coffee cups.

2. Transfer to the #56 Milwaukee, the artery of the Northwest Side.
Ride through real neighborhoods, past storefronts, bakeries, taquerias, barber shops, old bars, and new dreams.

3. Stay on the #56 until you reach the Jefferson Park Transit Center, where buses, personalities, and CTA lore collide.

4. At Jeff Park, you pay at street level. After the turnstiles, take the escalator down to the Blue Line platforms — that familiar CTA echo chamber below ground.
The Blue Line will carry you straight into O’Hare — steady, reliable, no drama.

⭐ Bonus Chicago Native Move: Lou Malnati’s for the Flight

If you’re feeling bold — or just hungry enough to defy the travel gods — hop onto a Pace suburban bus (yes, Pace) and head for one of the neighborhood Lou Malnati’s locations.

Order a proper deep-dish.
The kind with enough cheese to anchor a tugboat.

TSA will let solid food through security, though if the pie is still molten they may give you a look. If they wave you through, you’ve just secured the best in-flight meal on a 17-hour haul. Whatever the airline is serving doesn’t stand a chance.

It’s your call.
But if you pull it off, you’ll be eating like a Chicagoan at 30,000 feet.

And when the Blue Line finally delivers you into the bright hum of O’Hare, you’ll feel that quiet truth every Chicagoan carries:

You didn’t just visit Chicago.
You traveled it — the way a native does, the way the city wants to be known.

And that stays with you long after your plane lifts off the runway and the skyline shrinks into memory.

— Just Another Friendly Occupier

Featured picture AI Best Guess Rendering. Sometimes we ask too much of it.