Chicago Water Tower

Original Painting - Acrylic on canvas 20x20

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Holiday Shoppers

Original Painting - Acrylic on canvas 20x16

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Cold Chicago Rain

Original Painting - Acrylic on canvas 16x8

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Chicago Skyline at Sunset

Original Painting - Acrylic on canvas 30x40

Chicago Skyline at Sunset

I never tire of painting the Chicago skyline. The lights glitter and shine against a backdrop silhouette of towering buildings as the sun sets.

Chicago From Above

Original Painting - Acrylic on Canvas 24x30

From the air the lights of Chicago cast a magical glow skyward as gathering clouds form a dramatic backdrop. To the east, only the dark waters of Lake Michigan surge and swirl, seemingly as cold and black as deep space.

Rainy Night Blues

Original Painting - Acrylic on Canvas 20x16

A summer thunderstorm drenches the city and isolates the pedestrians under awnings and umbrellas to escape the downpour. Car tires swish through puddles on the wet pavement as the rain beats a steady tattoo on the city streets. The distant rumble of thunder joins the rumble of traffic and bright downtown lights challenge the sporadic flashes of lightning illuminating the dark sky above.

Chicago Raindrops on Glass

Original Painting - Acrylic on Canvas 16x20

Raindrops splatter against the window as thunder shakes the glass and rumbles across the dark and churning sky. The city looks as if it is underwater …a lost city of Atlantis beneath the waves. Watery lights gleam and flicker distorted by the droplets as they wriggle their way down the wet surface. It seems like a good day to stay snug and dry in your bed.

Downtown Chicago

Original Painting - Acrylic on canvas 40x30

Flashing lights, city traffic, pedestrians and noise are all part of the urban scene as the denizens of the concrete jungle prowl the streets.

Tooker Alley Chicago



Original Painting - Acrylic on canvas 20x16

One can almost imagine the denizens of early 20th century Chicago climbing over the garbage cans “down Tooker Alley to the Green Light over the Orange Door” to get to the famed Dil Pickle Club.

The club was almost hidden from the outside and was considered a "hole in the wall" in Tooker Alley. The entrance was marked by a "DANGER" sign that pointed to the orange main door which was lit by a green light. On the door, it read: “Step High, Stoop Low and Leave Your Dignity Outside.”

During the Great Depression, the Dil Pickle Club began to experience its decline. By the early 1930s, the club was being frequented more by Chicago mobsters rather than the usual free-minded Bohemian attendees of the earlier era.

Machine Gun Madam

Original Painting - Acrylic on canvas 16x12

“The voluptuous blonde bombshell just delivered a Chicago Valentine to a couple of wise guys trying to muscle in on her operation ...a hooker with a heart of hot lead instead of gold.”

I had a lot of fun painting this and learned a lot about the Thompson Submachine gun; also known as, the Chicago piano, the Chicago typewriter, Chicago Organ Grinder, and the Tommy Gun.

Gangsters and Bootleggers of the Prohibition and Depression era made this their weapon of choice. It has been referred to by one researcher as the "gun that made the twenties roar." The Thompson Model 1928 submachine gun came with a 20 or 50-round drum magazine and a .45 caliber punch.

This was the weapon used in the infamous Chicago St Valentine’s Day massacre where seven members of the North Side Irish Bugs Moran gang were mowed down by Al Capone’s South Side Italian gang.

Chicago Gold

Original Painting by Tom Shropshire

Acrylic on canvas 30x40



An impressionist view of Chicago after dark. The lights glitter and shine like a pot of gold against a backdrop of towering buildings. A light fog drifting in from Lake Michigan diffuses the golden glow and softens the edges of the skyscrapers. chicago cityscape canvas prints

Power Center

Original Painting - Acrylic on canvas 30x24

The Sears Tower, now named the Willis Tower, had the name changed under terms of the 2 million dollar lease agreement between the building owners and a London-based insurance company. To most midwesterners it will still always be known as the Sears Tower. But money is power, and in this painting the power lines converge on Chicago ...a not so subtle visual aid as to the center of power. chicago at night canvas prints

Chicago Fog

Original Painting - Acrylic on canvas 24x30
The fog rolls in from lake Michigan and covers the lower parts of the city while the tallest skyscrapers hold their heads above the swirling blanket. But the poet Carl Sandburg - Chicago Poems 1916, said it best;

Fog

The Fog comes

On little cat feet.

It sits looking
Over harbor and city
On silent haunches
And then moves on.

Rainy Days and Mondays

Original Painting - Acrylic on canvas 20x16

I always liked the Karen Carpenter song with the same title. The only difference is rainy days and mondays never get me down. I love rainy days ...the wetter the better. Rain storms have always made me feel invigorated and very creative. Painting on a stormy day is one of my favorite things. Curling up with a good book as the rain pounds on the roof is also right up there with my favorites.

This scene could be any big city in the rain such as New York, Chicago, or Milwaukee.

Chicago Moon

Original Painting - Acrylic on Canvas 30x40

A full moon over Chicago with the John Hancock Center in the foreground was a challenge and a learning experience. The moon was added midway through the painting and it controlled the painting from that point on. The sparkle and glitter of the city at night plus the moody sky combined for a dramatic show. Sometimes a painting lets you know what it needs if you just look and ask ...what if ? I'm glad I did. city scenes prints

Moon Over Third Street

Original Painting - Acrylic on canvas 20x16

I painted this as a companion piece to "Street Life". I had so much fun painting the seedy section of town teeming with life and vitality, that I was compelled to paint it again. I added the guys with the basketball for my grandson Joey because he's a dedicated basketball player and he really liked the last painting.

Street Life

Original Painting - Acrylic on canvas 24x20

This painting of a city street is completely imaginary but representative of any older run-down neighborhood in any major city such as New York, Detroit, Chicago, or Milwaukee. People are outside on the street to escape the heat of a summer night. Graffiti painted walls are the backdrop for a police stop gathering onlookers.The old brownstones lean together remembering a grander and more genteel time and place as hip hop music blares and sirens wail in the distance.  night city art

City Haze

Original Painting - Acrylic on canvas 16x12

Ghostly skyscrapers tower over older tenements on a hot summer morning in the big city.  city lights art

Navy Pier Ferris Wheel Chicago

Original Painting - Acrylic on canvas 16x20

(click on painting to enlarge)

The Navy Pier Ferris wheel in Pier Park was modeled after the first Ferris wheel built for the 1893 World’s Columbian Exposition in Chicago. It is the jewel of Navy Pier with its thousands of lights sparkling over the waters of Lake Michigan. Almost 300 people can ride the Navy Pier Ferris Wheel at a time, with up to six people in each of its 40 passenger gondolas. chicago art



The Chicago Theatre

Original Painting - Acrylic on canvas 16x20
(click on painting to enlarge)

This historic Chicago landmark first opened it's doors in 1921 and has thrilled visitors ever since. The last time I was there was for a performance of "Dirty Dancing", but the theater itself is the real show. See more landmark images; landmarks art