A hallmark Chicago dog shack, Portillo’s has expanded to multiple states from California to Indiana. Each of the 45 outposts has a different theme, whether ‘20s gangster or ‘30s Prohibition. Still, the W. Ontario flagship in Chicago offers a drive-through so you can get a classic dog on the run, piled high with mustard, relish, onions, tomatoes, pickle, and sport peppers on a poppy seed bun.