Dog daysChicagoland and Springfield, IL

Chicago sketch by Chandler O'Leary

This post is part of an ongoing series called 66 Fridays, which explores the wonders of old Route 66. Click on the preceding “66 Fridays” link to view all posts in the series, or visit the initial overview post here.

Okay, I’m starting this post with a few sketches that are not on Route 66, but that provide a good bit of context—which is to say, if you’re hankering for a roadside red hot on your travels, there’s no better place to go than Chicago.

There’s some debate as to the origin of the humble hot dog. There is the German frankfurter, of course, but what has become the ultimate American street food seems to have murkier beginnings. Various cities with German-immigrant roots lay claim to the invention, including New York (where sausages were served on rolls at Coney Island in the 1870s) and St. Louis. But thanks to the persistent legend that the modern dawg, as we know it, was first served at the World’s Columbian Exposition in 1893, Chicago has taken the story and run all the way to the bank with it.

Chicago sketch by Chandler O'Leary

Today, Chicago is the weenie capital of the world. Chicagoland Mom & Pop hot dog stands outnumber the city’s combined tally of McDonald’s, Burger King and Wendy’s franchises. And many of them, like the fabulous (and slightly creepy) Superdawg Drive-In above, have been mainstays for half a century or more.

Chicago sketch by Chandler O'Leary

And just like the infamous Hot Wiener Sandwich of Rhode Island, a true Chicago Dog wouldn’t be caught dead in ketchup.

I started with these non-66 hot dog stands so you could see how high Chicago sets the bar for its tube-steak signage. If these wiener masterpieces could be found across town from the Mother Road, imagine how high my expectations were for Route 66’s offerings.

Route 66 sketch by Chandler O'Leary

Well, I’m here to tell you, I didn’t come away disappointed.

Route 66 sketch by Chandler O'Leary

And if you’re heading west on Route 66, you’re in for an added bonus. Just when you think you’ve left the Dog Days behind, you’ll reach the state capital of Springfield and meet the Cozy Dog Drive-In. The Cozy Dog was founded by one Ed Waldmire, Jr. (remember the name Waldmire—there’s more 66 lore there to share another day), who, at a USO during World War II, invented the “crusty cur,” a cornbread-battered hot dog on a stick that would become a staple of State Fair cuisine. The recipe was an enormous hit with the troops, so in 1946 Waldmire rechristened his creation the Cozy Dog, and the rest, as they say, is history.

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