For a good, old-fashioned, rich-as-Croesus, ice cream, sundae, shake, malt, etc. in Chicago, Oberweis Dairy. They used to be exclusively in the western suburbs (seemingly one within shouting distance of every suburban station of the Burlington Northern commuter line) but they’ve diversified to all over the suburban area and even have a location in the city, in Lincoln Park (which totally surprised me). I’ve never gone past one that was open that wasn’t packed with customers.
“You LAers forgot ‘Tail o’ the Pup’ on San Vincente/Beverly in LA. Where else can you buy a hot dog out of a building shaped like a hot dog?”
How about two enormous hot dogs (one “male” and one “female”) standing on the roof, with arms and legs and faces and wearing a caveman outfit and a dress respectively? Superdawgs, at the “six corners” of Milwaukee, Nagle, and Devon in Chicago. It’s a real honest-to-Betsy drive-in: opened in the 1940s, squawk boxes, “girl” carhops, the tray that hooks on your window, ketchup in a red squirt bottle, and salt and pepper in shakers. They’ve serve hot dogs, burgers, and other sandwiches in a box packed full with french fries. My cholesterol level rose 10 points just thinking about it, but I’m also salivating like Pavlov’s dog.