Before Sonic popularized the concept of the fast-food drive-in in 1953, there was Superdawg, rising like a neon beacon over Chicago’s far northwest side. Since 1948, the retro restaurant has been an Americana pastime for Chicagoans and tourists alike, especially those looking for something a little more unique and a little less touristy than your typical downtown fodder. Founded by Maurie and Flaurie (aka Florence, again with the phonetics) Berman, Superdawg is in a league of its own when it comes to Chicago hot dogs. Unlike most Chicago-style dogs, these snappy bad boys come with onions, sport peppers, mustard, a pickle, and most originally, pickled green tomato for extra zing. It’s all bundled up neatly in a colorful, comic book-esque box alongside a bed of hot crinkle-cut fries. The drive-in format emerged out of convenience, as a way for cars to park by electronic speakers and place orders for carhops to deliver right to your window. Nowadays, Superdawg has another location in Wheeling and a few newer menu items, but the ritual of eating its namesake menu in your car remains as tried-and-true a Chicago pastime as any.
How to book: Delivery isn’t available, nor are advanced orders. Just park your car, roll down your window, and order away.