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From the Breakfast Counter to Last Call: Eating Chicago in One Day

Chicago, United StatesApril 21, 20252 min read
By MASA Editors
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A Chicago deep-dish pizza in its black pan on a wooden table, one slice lifted out01
A Chicago deep-dish pizza in its black pan on a wooden table, one slice lifted outPhoto: Dex Ezekiel / Unsplash

Italian beef, a hot dog that must never meet ketchup, deep-dish and tavern-cut pizza, and a jazz club that has been pouring since Prohibition.

Chicago eats like a city built by everybody. The dishes it guards most fiercely were invented for people working long shifts: portable, cheap, unreasonably good. Here is a day built entirely around them.

Key facts

  • The rules: no ketchup on a Chicago dog. Ever.
  • The two pizzas: deep-dish gets the fame, but tavern-style thin crust cut into squares is what locals eat more often.
  • Getting around: the "L" reaches most of these neighbourhoods; hours and closures vary, so check before travelling far.
  • Best months: May to October, when patios, rooftops and street festivals are open.

Breakfast: the counter, not the cafe

Start at Lou Mitchell's, a diner near Union Station that has been feeding travellers since the 1920s and still hands out doughnut holes to people in the queue. Order eggs in a skillet and pretend you have a train to catch.

Mid-morning: the Italian beef

Thin-sliced roast beef, seasoned gravy, sweet or hot giardiniera peppers, on a roll that is dipped back into the juices until it barely holds together. Al's No. 1 Italian Beef and Portillo's are the reference points. Order it "dipped, hot", stand at the rail, lean forward.

Aerial view of downtown Chicago's dense skyline at dusk with Lake Michigan stretching to the horizon behind the towers
Aerial view of downtown Chicago's dense skyline at dusk with Lake Michigan stretching to the horizon behind the towersPhoto: Pedro Lastra / Unsplash

Lunch: the hot dog, done properly

An all-beef frankfurter in a poppy-seed bun, then yellow mustard, chopped onion, bright green relish, tomato wedges, a pickle spear, sport peppers and celery salt. Superdawg keeps the drive-in tradition alive on the north-west side; The Wieners Circle serves them with a side of theatrical abuse.

Afternoon: sandwich city

Manny's Cafeteria and Delicatessen has been slicing corned beef since the 1940s and is still run on trays and shouted orders. If you would rather eat somewhere older still, The Berghoff has been pouring in the Loop since the 1890s.

Dinner: pick your pizza fight

Deep-dish is a casserole with ambitions: buttery crust, cheese under the sauce, forty minutes in the oven. Lou Malnati's and Giordano's are the classic pair, while Pequod's makes a pan pizza with a rim of caramelised cheese charred against the tin. For the local everyday version, find a neighbourhood tavern doing thin crust cut into squares.

Mister J's storefront advertises char-broiled chicken, Italian beef and burgers on a Chicago street corner.
Mister J's storefront advertises char-broiled chicken, Italian beef and burgers on a Chicago street corner.Photo: Alan Rodriguez / Unsplash

Late: a nightcap with history

The Green Mill in Uptown has been a jazz club since Prohibition, with Al Capone's preferred booth still pointed out to visitors. Locals may dare you into a shot of Malort, a punishingly bitter local liqueur. Nod, sip, regret nothing.

If you want the tasting-menu version

Chicago's fine dining is world-class: Alinea remains one of the most decorated restaurants in the United States, Girl and the Goat built its reputation on bold shared plates, and Kasama turned a Filipino bakery into a destination. Book weeks ahead.

Tip: Do not try deep-dish and Italian beef in the same sitting. Space them across the day, walk the lakefront between them, and you will make it to dinner.

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