I first met my wife Marilyn, a Chicago native, at a friend’s Halloween party in the Haight district of San Francisco. We clicked right away and spend the entire evening together. Since Marilyn was only visiting for a few days, I convinced her to extend her stay so we could spend more time together exploring the city and the California coast.

After the extended visit, Marilyn returned to this Chicago home where she lived with her grandmother. Several weeks later, I flew in to The Big Windy for a visit, staying for four snowy, sub-zero days during which we did precious little sightseeing. While we gazed out the window at the frozen snow, Marilyn told me that, hidden in their burrows until spring lived an abundance of black squirrels, and she hoped one day I’d be able to see them.

Last autumn, Marilyn’s grandmother passed away in this home she had owned for 40 years, and now Marilyn’s mom lives in Gram’s house. Marilyn and I, who now live in Sonoma County, visited Chicago recently and stayed in the house with Marilyn’s mom. And after five short days, I became convinced that in Chicago, squirrels outnumber humans.

Behind the house, a wooden deck provides an excellent view of those busy squirrels, and overlooks a yard where cardinals can often be heard, but rarely seen. The deck is surrounded by a colorful flower garden, where in the evenings, solar lights in whimsical shapes give off an inviting glow.

One afternoon, I carried a dining room chair to the front of the house to stake out a sketching spot. The air grew heavy with humidity as I drew, subsiding precious little in the fading afternoon. Cicada insects buzzed in crescendoing waves, louder than I ever imagined they could, then faded to silence.

The squirrels kept their distance, showing no interest in my drawing, but several groups of people were intrigued, including a woman and her daughter, a budding artist. I was happy to talk about my sketch of Gram’s house and to let the young girl know that sketching is all about having fun while learning.

As we exited the plane at O’Hare Airport, I felt a wave of heat and humidity wash over me, contrasting to our familiar Bay Area climate. “Welcome to summer in Chicago,” Marilyn called back with a smile. Although I’ve lived in hot climates before, my wife likes to remind me that Arizona is a dry heat and that I haven’t felt real heat until I’ve experienced it in combination with humidity.

Gathering our bags, we headed out to the curb and waited for Marilyn’s mom to arrive. After a cell phone call and a few minutes of honks, screeches, and exhaust, we were picked up and swept off to to lunch. Although it was only 10:30 am back home, we’d been up since 3:00 am and were already adjusted to our new time zone, hunger pangs and all.

On the corner of Talcott Road and Canfield Avenue, right on the dividing line between Chicago and suburban Park Ridge, is Nonna Silvia’s Trattoria and Pizzeria. We sat under a patio umbrella while enjoying lunch in the warm, but not yet hot, midday sun. Jetliners flew overhead, arriving at nearby O’Hare, engines roaring.

I ordered pollo con pesto, an open faced grilled chicken sandwich and a refreshing local ale called 5 Rabbit. The beer tasted of malt with a slightly hoppy finish and it replenished the water that had been extracted from my body during travel.

While drinking beer and waiting for my lunch to arrive, I reached for my sketchbook and drew Marilyn sitting next to me and then began another sketch of my lunch, starting with my beer and making sure to leave room on the page for a plate. When my sandwich arrived, I added it to my sketch but soon hunger won over and I set my sketchbook aside. Taking a picture of my meal for later reference, I then devoured my sandwich.

A rogue gust of wind came out of nowhere and blew over the patio umbrella next to us causing a stir, but thankfully there were no injuries. The wait staff asked if everyone was okay and secured the umbrella upright, this time leaving its canopy closed. Welcome to The Windy City.

While visiting Chicago, I told my wife I wanted to hear live jazz in a smoky old club without the smoke. As a native Chicagoan, she’d visited the Green Mill in the Uptown neighborhood many times. We checked online to find the Pharez Whitted Quintet would play that weekend. So, after a Friday night home cooked meal, we ducked out to hear the show.

In a cozy booth hugging the main room’s wall, Marilyn sipped cranberry juice while I enjoyed a pint of beer. It was almost too dark to see the marks on the page, but even still, I sketched through the evening. Dimly lit art nouveau chandeliers provided ambiance, lighting rococo framed murals. In keeping with the club’s décor, an alabaster statue of Ceres, the Goddess of Harvest (whom house musicians have rechristened “Stella by Starlight”) stands just to the left of the stage.

The Green Mill opened in 1907 as Pop Morse’s Roadhouse and was used as a place for mourners attending service at nearby St. Boniface Cemetery. In 1910, new owners converted the roadhouse into an indoor/outdoor club for dancing and drinking, modeled after The Moulin Rouge Gardens, renaming it Green Mill Gardens. Musicians Al Jolson, Eddie Cantor and Sophie Tucker all performed here. The table just across from us (bottom left of my drawing) was frequented by Al Capone and his bootlegging henchmen, and tonight, the table was ironically covered with glasses filled with wine and booze.

The band kept our feet tapping until the early morning hours. I would best describe the sound of Pharez Whitted as straight-ahead jazz, but Neil Tesser of the Chicago Examiner gives a better description, “Pharez . . . honors the late giant (Freddie Hubbard) with his combination of intensity and technique, spank and sparkle, and that hot-cider tone!” I’ll buy that.

Wrigley Field was near the top of my Chicago to-do list. On our first day out driving, I asked to see the famous stadium, with no idea it just happened to be nearby. I knew there’d be a game in progress so traffic might be a problem. My wife pulled into the McDonalds parking lot across the street from the stadium and my mother-in-law popped in for a soda (or “pop” as they say in the Midwest). I asked Marilyn if I had enough time for a quick sketch; she smiled and nodded yes. Jumping out of the car, I then began to draw at a frantic pace. The game was in progress, and “Take Me Out to the Ball Game” was being played and sung. We had just happened to catch the 7th inning stretch. A bit later, in the bottom of the inning, cheers erupted as the Cubs knocked in another home run, reaching what was to be the final score: Cubs 7, Brewers 1.

Chicago has a great public transit system known as the CTA and my wife and I used it almost every day during our visit. While riding the Blue Line train on our way to Millennium Park down town, I sketched this guy with his blond mass of hair hanging down over his face and reading the sci-fi book Dune. I used ink, colored pencils, and my watercolor kit with a waterbrush to add color as we zipped along. The interior bus drawing (22 Clark) was added another day while visiting Andersonville, a neighborhood of Chicago.

While glancing at a Chicago newspaper’s calendar of events, I noticed that in just two days Roger Ebert would be signing his new book Life Itself at a local Barnes and Noble. We planned to arrive early that evening, expecting a crowd. I didn’t know whether Roger would allow pictures or drawings of him, so while waiting, I began sketching two comfy chairs, one of which was to be occupied by Roger. Before he and his wife Chaz arrived, promptly on time, I’d also had time to add the backdrop to my drawing. We all quickly felt a distinct part of the experience, as Roger walked straight up the queue of his fans, stopping to shake each one’s hand. He also took a moment to look directly at each person’s eyes, as if to etch their face into his memory, or perhaps simply to acknowledge everyone individually. It was a touching experience. Someone in the crowd asked if photographs of Roger were allowed, and Chaz, who was also there to help, replied in the affirmative. After he signed my book, I stood back a bit and sketched Roger as he continued to sign books. What an amazing person he is.

**UPDATE September 10, 2012**

Roger Ebert will have a documentary made about his life, based on his book, Life Itself, with Martin Scorsese producing the film. Scorsese has optioned Ebert’s book, Life Itself and Hoop Dreams’ Steve James will direct.

From Suntimes.com:

“When I first learned they were interested, the news came out of a clear blue sky,” Ebert wrote in an e-mail. “I once wrote a blog about Steve James’ “˜Hoop Dreams,” calling it the “The Great American Documentary.” His “˜The Interrupters,” about volunteers trying to stop street violence in Chicago, is urgent and brave. Now to think of him interested in my memoir is awesome. Zaillian and Scorsese are also brilliant filmmakers. I couldn’t be happier, especially since I never thought of “˜Life Itself” as a film.

**UPDATE April 4, 2013**

Roger Ebert passed away today. He will be missed.

Marilyn drove us to Andersonville to meet a friend she hadn’t seen in many years. Tim, a native Chicagoan who’d lived briefly in Michigan, had returned to Chicago a couple years ago. We met at Kopi Cafe — my kind of place with its great coffee and desserts, and eclectic décor. We sat in the warm front section, on floor pillows around a low table, and 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.