Tastee Freez/Cal’s Creemy Whip/Toot’s Drive-In

During the 1950s Chicago had a bunch of ice cream drive-ins called Tastee Freez. Our local branch was located on the southwest corner of Montrose and Central.

Everyone had a personal Tastee Freez treat. Mine was the dip-top, vanilla ice cream covered with frozen chocolate syrup, served in a square cone. However, I usually bought a sundae because of the premium attached to the dish—little plastic statues of presidents or baseball players or Jesus and his twelve apostles.

Around 1965 the shop became known as Cal’s Creemy Whip. Cal’s last name was Hilton, and he claimed to be related to James Hilton, the famous author of Lost Horizon and other novels. I don’t know whether Cal was telling the truth. I also don’t know whether he misspelled “creamy” on purpose.

Cal eventually sold out. The place was spiffed up and became Toot’s Drive-in. By that time I’d moved out of Portage Park, so I stopped by only occasionally. Toot’s closed a few years ago, and the old building was finally leveled. There’s a more “modern” restaurant on the site now.

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