The original Italian beef since 1938, and the place where the arguments about how to order one are settled by the counter staff with a speed and impatience that leaves no room for indecision. Italian beef is Chicago's greatest sandwich — thinly sliced roast beef, slow-cooked in a gravy of Italian spices, piled onto a long Italian roll, and topped with sweet peppers or hot giardiniera (or both). The 'dipped' option means the entire sandwich is dunked in the gravy until the bread saturates and begins to dissolve, which sounds like a mistake but is actually the point. Al's invented the format and the Taylor Street location has served it unchanged for the better part of a century.
Location
Little Italy, Chicago
Insider Intel
Italian beef, dipped, with hot giardiniera. This is the correct order. 'Dipped' means the assembled sandwich is submerged in the jus/gravy before being handed to you; the bread absorbs the liquid and the structural integrity becomes a race against time. Hot giardiniera adds the vinegary, spicy crunch that the soft, wet sandwich needs for contrast. Sweet peppers are the alternative for those who cannot handle heat. Eat it leaning forward over the counter — the drip is inevitable and part of the experience.
Weekday lunch at 11:30am when the line is short and the beef is fresh from the morning cook. Weekend afternoons draw longer lines but move quickly — the counter staff operate with the efficiency of people who have been making the same sandwich for decades. The Taylor Street location is the original; other locations exist but this is the pilgrimage.
Counter service only. The line moves fast because the ordering process is designed for speed — know what you want before you reach the counter. Cash and card. No seating inside; you stand at a counter or eat in the small outdoor area. The Taylor Street location is in Little Italy, near UIC, accessible by the Blue Line at UIC-Halsted. The sandwich is messy by design — do not wear anything you value. Italian beef and a Chicago-style hot dog from the same counter is the double-header order for the ambitious.