Chicago looks friendly from a distance—gleaming lake, skyline like a row of trophies—but the city asks a little grit in return. Here, winter is a contact sport, the wind has a nickname, and your neighbors will judge your snow-shoveling form like Olympic judges. The “L” squeals, the roads heave, and everyone still somehow shows up on time with salt on their boots and a grin. If any of the following make you flinch, the city might politely suggest you visit in July and leave it at that.
25. The Hawk will find the gap in your scarf
That legendary wind slices between buildings and right through optimism. If you don’t know how to turtle your whole face into a beanie, you’ll learn by noon. Lotion is strategy, not vanity. And yes, the wind chill is real and rude.
24. Lake-effect weather whiplash
Sun, sleet, sideways snow—sometimes in the same hour. Veterans carry sunglasses and a knit hat in the same pocket. Talking about the forecast is not small talk; it’s tactical planning. If you melt at 38°F and drizzle, January will eat you.
23. “Dibs” is sacred law
Shovel out a spot and you’ll guard it with a folding chair like it’s crown jewels. Outsiders think it’s petty; locals call it justice by back pain. Violate dibs and you’ll learn new vocabulary from the entire block. A lawn chair can hold more power than City Hall.
22. Shoveling is judged like a sport
Your technique, your edges, your attention to the sidewalk seam—all noted. Leave an icy ridge and you’ll hear about it from strollers and seniors alike. Good neighbors salt generously and clear the whole frontage. If you only shovel your car, you’re not from here.
21. CTA patience and platform grit
You’ll wait on an open-air platform with eyelashes freezing together. Trains arrive full, brakes sing, and everyone still slides in with Midwestern efficiency. Don’t block the doors; don’t monologue on speakerphone. If the heat lamps scare you, the Red Line in February will finish the job.
20. The grid is your compass, not your crutch
Addresses count by hundreds, and “East/West of the river” is a worldview. Say “go north on Milwaukee” and expect diagonals and mild chaos. Real Chicagoans give directions with intersections, not vibes. If you need a scenic route, take a boat.
19. Deep dish is a holiday, tavern-cut is life
Tourists worship casserole-thick pies; locals order cracker-thin squares on weeknights. If you can’t respect both, you’ll dine alone. Tomato-on-top isn’t a prank—it’s tradition. Bring napkins and opinions.
18. No ketchup on a hot dog, ever
This is not a debate; it’s a municipal ordinance of the soul. Mustard, relish, onion, sport peppers, pickle spear, tomato, celery salt—load it up. Ask for ketchup and you’ll get a side-eye strong enough to bend steel. You may have it on fries; we’re not monsters.
17. The Italian beef cuts both ways
“Hot” means giardiniera, “sweet” means peppers, and “dipped” means you’ll need forearms. If you eat it with a fork, we’re calling your emergency contact. The bread should sag with dignity. Wear dark colors and accept your fate.
16. Malört separates tourists from citizens
One shot tastes like grapefruit peels and consequences. We clink, we wince, we laugh, and we carry on. The “Chicago Handshake” isn’t delicious; it’s communal. If you refuse it outright, enjoy your suburban exile.
15. It’s pop, gym shoes, and “the Jewel”
Language here has its own zip code. Ask for “soda” in your “sneakers” and we’ll translate with a smile. The front room is the “frunchroom,” and yes, we know how it sounds. You’ll adapt or you’ll order wrong forever.
14. Neighborhoods mean something
Rogers Park is not Logan Square, and it is not Bridgeport. Everyone has a corner bar, a favorite bakery, and a festival they’ll defend like family. Cross-town trips are planned like expeditions. If you say “I live in Chicago” but can’t name your ward, try again.
13. The lakefront is a year-round gym
Runners crunch across snow, cyclists flirt with wind, and polar plunges are love letters to chaos. In July, the trail becomes a parade of sunblock and smiles. If your “beach day” requires 80°F, you’re missing half the year. The Lake is a church; dress accordingly.
12. There are two seasons: winter and construction
Orange cones blossom the moment the thaw hits. Lanes vanish, ramps reroute, and every driver becomes a philosopher. You will recite the names of expressways like saints. If detours break your spirit, wait till the Kennedy closes a lane.
11. Airport fluency is a survival skill
O’Hare delays are a rite, not a surprise. You should know which Blue Line car gets you closest to your terminal. Midway will charm you and still steal your time. If you budget “exactly 28 minutes,” you’ll miss Thanksgiving.
10. Street festivals every weekend, like clockwork
From June through September, every block has bands, brats, and beer lines. You’ll donate at the gate with a folded five and call it civic pride. Learn to navigate wristbands, dog strollers, and funnel cake crosswinds. If crowds make you wilt, find a shady porch and wave.
9. Patio season is a 48-hour window
The first 65° day turns the city feral with joy. We sit outside in coats, clutching drinks like trophies. If you wait for perfect weather, you’ll age out of summer. We bask at the faintest hint of sun.
8. Layering is an art form
Base, mid, shell, confidence—repeat. Wet socks are a moral failing; wool is salvation. Gloves live in every pocket, just in case. If you think a hoodie solves January, bless your heart.
7. The alley system is its own ecosystem
Trash, recycling, brown rats, garage bands, and impromptu parties—welcome to the backstage of the city. You’ll learn bin days and rat-proofing faster than your Wi-Fi password. Garages are social spaces with folding chairs and suspiciously good speakers. If alleys scare you, stay on the boulevard.
6. Vintage radiators and back porches
Steam heat clanks like a percussion section, and windows leak like gossip. Three-flats come with wood porches that creak, host barbecues, and occasionally lean. You’ll master the window fan inversion ritual by June. If central air is a must, bring your checkbook.
5. Tickets, stickers, and boots—oh my
City stickers, permit parking, street cleaning—miss one sign and your car learns humility. Parking apps become reflexes. We accept tickets the way sailors accept waves. If that sounds unfair, welcome to adulthood.
4. Lines you must earn the right to complain about
You will wait for burgers, birria, bread, or Alinea’s wizardry. We gripe, we post, we eat, we forgive. Great food is a hobby and a contact sport. If “first-come, first-served” offends you, pack a snack.
3. Sports heartbreak as a dialect
“Maybe next year” is both a curse and a lullaby. Bears’ winters are long; Bulls’ summers are nostalgic; baseball splits the family group chat. We still tailgate in sleet because hope is hydrating. If you need guaranteed rings, try a catalog.
2. Midwestern nice with steel inside
We’ll hold the door, push your car, and check on your grandma. But we’ll also tell you—kindly—to move down the car and stop blocking the aisle. Polite doesn’t mean soft; it means efficient. If you confuse kindness for weakness, the city will educate you.
1. Loving it anyway
Chicago tests you, then hands you a sunrise over the lake that fixes your whole week. It tears up your shins with ice pellets and still gets you home for a neighborhood beer. You learn the rhythms, the shortcuts, the jokes—and suddenly they’re yours. If that sounds like work, it is; if it sounds worth it, welcome.
