Superdawg opened its doors on the corner of Milwaukee, Devon, and Nagle Avenues in 1948 and became an instant success, wowing Chicagoans with its slightly spicy hot dogs topped with picked green tomato. Today, the classic drive-in still maintains its rep as one of the best spots for hot dogs in the city. You can order from the takeout window or grab one of the small handful of indoor seats, but we suggest you go full-on '50s and pull up to one of the carports and order through the retro call box. You'll want to go for the Superdawg, served on a poppy seed bun and dressed with golden mustard, tangy piccalilli, kosher dill pickle, chopped Spanish onions, and a hot pepper. It comes with a side of scrumptious crinkle-cut fries, too.