Exploring Downtown Chicago and Beyond


Exploring Downtown Chicago and Beyond

[By Richard Sheppard in Chicago, Illinois] 

Accommodations for the Urban Sketchers Symposium can be quite comfortable if you have a friend who’s nice enough to use thousands of accumulated Marriott points. My friend Phil had enough points to score the Blackstone Hotel, just two blocks from the Goodman Center where the Symposium was centered in downtown Chicago. Thanks Phil!

The historic hotel was built by the Drake brothers, hiring architects Marshall & Fox to design it. It opened in 1910 and at the time it was the tallest building in Chicago. Noteworthy guests have included 12 consecutive presidents from Taft to Carter, Al Capone, and others. The Blackstone has also been used as staging for several notable films, including The Color of Money and The Untouchables.

The narrow view we had out our 19th floor room included Grant Park and Lake Michigan off in the distance where two of my Symposium classes were held (Thanks Shari and Virginia!).


Across the street from our hotel was Grant park where the city of Chicago runs a free SummerDance series (with live band and instructors included) that’s available for anyone with two feet. So, why did I draw this food stand instead of the dancers? They showed up in droves about the time I was wrapping this painting up.
Once the Symposium was over, it was time to explore more of the great city of Chicago. Since the Symposium took every ounce of time and energy I had, I was glad my mother-in-law invited us to stay with her, rest up, and explore this amazing city beyond the downtown area.
The house my wife Marilyn grew up in.
One thing I’ll always remember about my visit to Chicago is this antique clock in a corner of my mother-in-law’s living room. Its art deco styling and colors are what attract me most, along with soft chimes that dance each quarter hour. The clock has been passed down for generations, and no doubt will be treasured by family clock keepers to come. It makes this corner a special place where I’d like to spend a day with a good book and a cup of tea.
Although I enjoyed the pizza at several downtown restaurants (including Exchequer) while at the Symposium, my favorite pizza restaurant in Chicago is still Pizzeria Uno. My wife and I went there on a Tuesday afternoon to avoid the crowds and were seated at a table with a view. I couldn’t have been happier. I placed my order for a Numero Uno “the works” pizza with sausage, pepperoni, onions, peppers, mushrooms and Uno’s unique chunky tomato sauce–topped with mozzarella and grated Romano. Then I began to draw my place setting, leaving space to sketch in my pizza when it arrived.
Deep dish pizza was invented in Chicago and Pizzeria Uno’s claims they introduced it to the world. But as with any number-one-claims-to-fame, there are controversies surrounding who actually owns the top spot. But who am I to argue? I just want a great tasting Chicago style deep dish pizza.

Chicagoans are proud of their public transit system, the Chicago Transit Authority (CTA), and they should be. Since the late 1940’s, the CTA has been providing a reliable, economical, and relatively safe way of getting around the city. The buses and trains we’ve used while here have been on time, clean, and an enjoyable way to travel.

While waiting for the bus to arrive, Marilyn and I played footsie at the station. I started to sketch our feet but it wasn’t long before the bus arrived and cut my drawing time short. Once we found a seat, I used my water brush to add some quick color to the line work. The bus took us to a train, which then left us at our final destination, the Art Institute.


Surprisingly, independent coffee houses (other than Starbucks) are hard to find in Chicago. But Copi Cafe in Andersonville is a nice alternative to the usual cup-o-joe. There we met an old friend of Marilyn’s, Tim, a native Chicagoan who’d lived briefly in Michigan, had returned to Chicago a few years ago.

We sat on floor pillows near the front window where we could watch the rain. After ordering a double Americano, I joined the discussion on politics, movies, and more. Marilyn asked Tim about his Lobster Butter Love t-shirt, which, it ends up, is RoosRoast’s signature blend coffee from Ann Arbor.
My trip to Chicago wouldn’t feel complete unless I visited Wriggly Field to watch the Cubs play. It was a good day for the Cubbies because they beat the Arizona Diamondbacks 12 to 4. Hot dogs and peanuts for everyone.
Although I’m not a huge hot dog fan (though I loved the one I had at Wriggle Field), I occasionally get a craving that just won’t let up. One afternoon as we drove past the cool vintage sign for Superdawg, a fire was lit in my belly and an image of a hot dog was etched into the craving side of my brain in glowing neon.

As we pulled up to park at the restaurant, I noticed the glowing retro menu at the passenger side. So Superdawg wasn’t just a diner, but a true old fashioned drive-in. Supercool! I hadn’t been to a drive-in restaurant since I was a kid. We parked and I rolled down the passenger side window to read the menu.

The array of choices was dazzling. Not only did they have Superdawgs but they also had: Whoopskidawgs, Whooperburgers, Superchickenmidgees, Supertamales, Superonionchips, Supermalts, and Supersundaes! The selection was a mind spinner, but what made my taste buds really stand at attention was a good ol’ fashioned hot dog with mustard. (In this town, I’m told ketchup on hot dogs happens about as often as peanut butter on eggs.)

I pressed the service button on the Order-Matic to request a Superdawg with fries and a Coke. Ten minutes later, a cheerful carhop fastened a full tray to the driver’s side window.

Marilyn passed me a drink and a cardboard box that, when opened, was stuffed full of ridged fries and, of course, a hot dog. I dove in, and before my wife could ask how it tasted, it was gone. “That was super!” I said. “But without pickles or onions, it’s not a REAL Chicago dog,” she quipped. “I wanted a Superdawg, not a superpickle,” I told her.

What could she say to that? The answer, my friends, is not much. And with that we flipped the tray pick-up switch on the Order-Matic and were on our way.


While shopping just north of Chicago near Lake Michigan, I began to realize that the end of my Chicago visit was near: there was only one day left to sketch the city. After browsing around downtown Evanston, we headed toward Northwestern University, driving amongst the ivy-covered buildings.
As we pulled into an outdoor parking lot, I spotted a clear and complete view of downtown Chicago. My spirits lifted as I left the car, sketchbook in hand, and strolled closer to the shoreline for the best vantage point.
Listening to the gentle splash of shallow waves against the steel pier, I watched clouds gather in dark formations miles east, above Lake Michigan, then watched as sheets of rain poured into the lake. I could have sat there for hours soaking up the view and listening to the waves. What a peaceful yet energizing way to cap off my time in Chicagoland.



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