Tag Archives: Chicago

Chicago Theatre sketch by Chandler O'Leary

Magnificent Marquee

When I was in Chicago last summer, I finally got to cross a big thing off my sketching wish list: the iconic lights of the Chicago Theatre. By the time I was done, I couldn’t help but wish that every city had its name inscribed on a giant, gorgeous neon marquee. I mean, I-Heart-NY shirts are nice and all, but if I were New York, I’d rather see my name in lights.

Chicago sketch by Chandler O'Leary

Dog days

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.

Lou Mitchell's sketch by Chandler O'Leary

The first stop

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.

If you’re going to start Route 66 in Chicago, start your trip right with a meal at Lou Mitchell’s diner. Nicknamed the “first stop on the Mother Road,” I can’t think of a better place to break your fast or mark the beginning of a journey. Also, since the place opens at 5:30 on weekday mornings, you don’t have to derail your whole day with a stop here. (Tangent! One of my few complaints about living on the West Coast is that nothing opens early. A huge thing I miss about Midwestern living is being able to run errands and go out to eat at the crack of dawn!)

Lou Mitchell's sketch by Chandler O'Leary

And if you go, you best come hungry. Not only are the plates enormous (double-yolk eggs!), but even the simplest breakfasts turn out to be five-course meals there. Leave room for the doughnut holes, is all I’m saying.

Lou Mitchell's sketch by Chandler O'Leary

Now, the food and history are reason enough to eat at Lou Mitchell’s. But the icing on the proverbial cake, for me, was the lettering. Hoo boy, there is more gorgeous, vintage, hand-painted sign lettering in there than can be found in some entire cities. I thought I’d died and gone to heaven.

Lou Mitchell's sketch by Chandler O'Leary

All I can say is thank goodness this place is still here, still largely untouched. It seemed like a good omen for embarking on an Americana pilgrimage. Long live Route 66, long live Lou Mitchell’s.

Route 66 sketch by Chandler O'Leary

Eastern terminus

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.

To help you keep your bearings in this 66 Fridays series, and to provide an overview of the route, the first few posts will go in geographical order. So let’s start at the very beginning, at the eastern terminus of the route.

American highways, in general, are measured from south to north, and from west to east. So in general, the “start” of any highway is technically its southern- or westernmost point, and the milemarkers count from there. But for our Route 66 trip we went from east to west. That’s because for that highway, at least, most travelers (from Dust Bowl migrants to pleasure cruisers) seemed to head that direction. All the Route 66 lore, from songs to stories, seems to be oriented that way, too. And besides, America is steeped in the tradition of heading West—to me, the East still feels like a beginning, and the West a promise of what lies ahead.

So that put the beginning of our journey at the beginning of the route: in downtown Chicago.

Chicago sketch by Chandler O'Leary

Route 66’s path through Chicago has changed somewhat over the years, but that’s a longer story than necessary for this post. To make things simpler, most travelers and historians count Michigan Avenue, between Adams and Jackson, as the eastern terminus of the Mother Road. (Adams is a one-way heading west, and Jackson is the same eastbound, hence the two intersections.) And there are no better guardians of the route than the bronze lions prowling in front of the Art Institute.

Chicago sketch by Chandler O'Leary

It’s even more fitting when you consider that the Art Institute was originally part of the 1893 World’s Columbian Exposition. A sort of World’s Fair, the Exposition marked 400 years since Christopher Columbus landed in the New World, and celebrated the rebirth of Chicago after the Great Fire of 1871. Most of the buildings erected for the Exposition were designed to be temporary, but the Art Institute was intended to occupy what was the World Congress Auxiliary Building at the fair, so that structure was made permanent.

Oh, and incidentally, the Art Institute of Chicago was originally called the Chicago Academy of Design, which was founded in 1866. Its address before the Great Chicago Fire? 66 West Adams Street.

Route 66 sketch by Chandler O'Leary

Somehow, then, it seems pretty perfect that an old WCE building, originally designed to promote westward exploration and new beginnings at the fair, marks the beginning of America’s best-known westward highway.

Chicago sketch by Chandler O'Leary

Detour

For as disorienting as being awoken before dawn by owls can be, it’s nothing compared to how it feels when you suddenly find yourself on the opposite end of the country than you planned to be. When you’re expecting to land in Houston, and what you get is a hurricane in your path, a sudden 2000-mile detour, two hours in the airport ticket line, a guardian angel having two phone conversations at once, and a surprise overnight trip into the heart of the wrong city—there’s definitely an overwhelming sense of “Okay, what just happened?”

All I could do was what I always do: get out the ol’ sketchbook, and enjoy the view.