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The list · Restaurants · Chicago

Ten Chicago Restaurants, and the Order to Eat Them In

Deep dish, Italian beef, a hot dog from a drive-in and two rooms you book weeks ahead. A list you can work through in a long weekend.

MyCheck · Sep 18, 2026 · 3 min read

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Chicago's food identity rests on a few specific things — deep-dish pizza, the Italian beef sandwich, the Chicago-style hot dog — and on restaurants that have stayed in one place for decades. This list mixes those with a handful of the city's better-known dining rooms, and puts them in an order that works: the ones you need to book come first, because the booking is the hard part.

Tick each place as you eat there. When you save the list, the ticks come with you into MyCheck.

Book these first

Stop 01

Alinea

Lincoln Park · 1723 N Halsted St, Chicago, IL 60614

Alinea is one of a small handful of three-Michelin-star restaurants in the United States, and its seats are sold as tickets through Tock rather than taken over the phone. They go weeks ahead. If it is on your list at all, it is the first thing to arrange, and everything else fits around the date you get.

Stop 02

Girl & the Goat

West Loop · 809 W Randolph St, Chicago, IL 60607

Stephanie Izard's restaurant has been on Randolph Street since 2010, one of the first on what became the West Loop's restaurant row. It takes reservations and they are worth taking a week or so out; walking in on a Friday is a long wait.

Stop 03

Gibsons Bar & Steakhouse

Gold Coast · 1028 N Rush St, Chicago, IL 60611

A Rush Street steakhouse open since May 1989, serving beef under its own USDA prime certification. It is the kind of room where the portions are the point and the bar is half the reason to go. Book, but a same-week table is usually possible.

The counters

Stop 04

Al's #1 Italian Beef

Little Italy · 1079 W Taylor St, Chicago, IL 60607

The Taylor Street stand of an Italian beef shop that dates itself to 1938. Order it "wet" — dipped in the jus — with hot giardiniera, and eat it standing up, elbows out, the way the counter is built for. There is no version of this list without it.

Stop 05

Portillo's (River North)

River North · 100 W Ontario St, Chicago, IL 60610

Portillo's started in 1963 as a Villa Park stand called The Dog House and now has locations across the country, but the River North one, open since 1994, is the one to visit: Chicago-style hot dog, Italian beef, and a chocolate cake shake that people order without irony.

Stop 06

Manny's Cafeteria & Delicatessen

Near West Side · 1141 S Jefferson St, Chicago, IL 60607

Manny's is a cafeteria-style Jewish deli open since 1942. You take a tray, the counterman hand-carves the corned beef in front of you, and you pay at the end of the line. It is on Jefferson, south of the Loop, and it is worth the detour on any day that is not a Sunday.

The pizzas

Stop 07

Lou Malnati's Pizzeria

River North · 439 N Wells St, Chicago, IL 60654

Lou Malnati's is deep dish: a family business whose first pizzeria opened in Lincolnwood in 1971, now with ten rooms in the city. The River North one on Wells Street is the easiest to reach and takes a reservation. Order the Malnati Chicago Classic and expect to wait forty minutes for it — that is not slow service, that is the pizza.

Stop 08

Pequod's Pizza

Lincoln Park · 2207 N Clybourn Ave, Chicago, IL 60614

Pequod's is the pizza you will argue about. It is pan pizza with a ring of mozzarella laid against the pan so it caramelises into a dark, chewy rim; Burt Katz opened the first one in Morton Grove in 1971, and the Lincoln Park room on Clybourn is where the city goes for it now. Some people think it is better than deep dish. Go and have the argument.

Michigan Avenue

Stop 09

The Purple Pig

Magnificent Mile · 444 N Michigan Ave, Chicago, IL 60611

Mediterranean-inspired small plates just north of the river — a useful stop if you are already walking the Magnificent Mile and do not want to plan a dinner around it. Book if you can; it is busy from six.

The drive-in

Stop 10

Superdawg Drive-In

Norwood Park · 6363 N Milwaukee Ave, Chicago, IL 60646

Superdawg has been at Milwaukee and Devon since May 1948, and it is still served to your car by a carhop, under two hot-dog figures standing on the roof. It is on the far Northwest Side, which means a car or a long ride on the Blue Line and a walk. Save it for the last day, and go.

Before you go

Hours and menus change. Every address on this list was checked against the restaurant's own website on the date at the top — and on the way, two ZIP codes that older lists get wrong were corrected. If something here has changed, say so in the comments and it will be fixed.

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