How to Draw Chicago Art

What You'll Need

• •Sketchbook or smooth heavyweight paper, plus an H or HB pencil, ruler, kneaded eraser, and fineliner for measured construction and crisp architectural edges
• •Watercolor, gouache, colored pencils, or markers in warm brick red, ochre, cream, brown, charcoal, muted teal, and subdued blue
• •A small set of flat and round brushes, including a narrow brush for terra-cotta details and window mullions
• •Drawing tablet or mouse with digital painting software that supports layers, selections, vector or shape tools, and perspective guides
• •A photo reference folder containing Chicago street elevations, masonry textures, window grids, cornices, terra-cotta motifs, and overcast or softly lit skies
• •Optional: a lightbox or tracing paper for testing facade variations before committing to the final composition

Step by Step

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   1. Choose a strong architectural composition

   Begin with a tall page or canvas and place the main building slightly off-center so the facade has room to breathe. Combine one dominant vertical mass with lower forms that extend horizontally along the street, creating the tension between steel-frame height and Prairie horizontality. Reserve a simple strip of sky and a narrow foreground street; the building should occupy most of the image. Avoid filling the first sketch with details, because the silhouette and proportion must work before ornament is added.

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   2. Establish horizon and perspective

   Draw a horizon line at about eye level and mark one or two vanishing points, depending on whether you want a frontal facade or a corner view. Use light construction lines to aim roof edges, sidewalk lines, window rows, and cornices toward the appropriate vanishing point. For a convincing street-corner composition, keep vertical edges nearly vertical while allowing horizontal edges to converge. Check the width of each floor against the perspective grid before darkening any lines.

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   3. Build the steel-frame massing

   Block the tower as a stack of clear rectangular volumes rather than as a single flat silhouette. Emphasize vertical piers at regular intervals to suggest the hidden steel frame, then interrupt them with horizontal spandrels or floor bands. Let the central shaft rise above a lower, wider base to create a readable skyscraper hierarchy. Keep the structural rhythm consistent, but vary the base, middle, and crown enough to prevent a mechanical repetition.

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   4. Construct the plate-glass window grid

   Divide each facade bay into repeated window modules using evenly spaced mullions, with slightly smaller modules near corners or recessed sections. Make the grid lighter and thinner than the structural piers so the facade reads as glass held by a frame, not as a wall covered in black lines. Add a few selective reflections as broad pale shapes rather than drawing a separate reflection in every pane. Use darker windows near recesses and warmer, lighter panes where the flat daylight strikes directly.

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   5. Add masonry, Prairie bands, and terra-cotta ornament

   Introduce warm masonry around the window grids with horizontal courses, broad belt courses, parapets, and projecting cornices. Use long, low bands at the base and intermediate levels to reinforce Prairie horizontality without reducing the building's height. Place terra-cotta ornament at meaningful transition points such as entrances, spandrels, capitals, and the crown; geometric leaves, stepped patterns, rosettes, and chevrons work especially well. Simplify each motif into a few repeatable shapes, because controlled rhythm is more convincing than intricate random decoration.

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   6. Design a geometric stained-glass focal point

   Choose one entrance transom, lobby window, or upper-floor panel for a concentrated stained-glass accent. Divide it into geometric rectangles, diamonds, arcs, or fan shapes with strong lead lines, then fill the sections with muted amber, teal, blue, cream, and rust. Keep the stained glass flatter and more saturated than the surrounding facade so it becomes a focal point. Repeat one or two of its colors elsewhere in small accents to connect it to the whole composition.

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   7. Apply the warm masonry palette

   Lay in large color families before adding texture: brick red or russet for masonry, ochre and cream for terra cotta, charcoal-brown for deep structure, and restrained blue-gray for glass and shadows. Mix neighboring warm colors instead of using a single flat brown, but keep the overall value pattern simple and readable. Save the darkest values for window recesses, doorways, joints, and a few strong structural lines. Test the piece in grayscale; if the facade still reads clearly, the color organization is working.

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   8. Finish with flat Midwestern illumination and selective detail

   Use broad, soft-edged planes of light rather than dramatic spotlighting or glossy high-contrast effects. Place a pale, nearly even sky and let one side of the building receive a gentle warm light while the opposite side shifts slightly cooler and darker. Add restrained sidewalk, street, and distant-building shapes to anchor the architecture without competing with it. Finally, sharpen only key corners, entrance details, window groupings, and ornament; leave secondary areas quieter so the finished image feels designed rather than overworked.

Going Digital

Work in layers for perspective guides, structural drawing, windows, masonry, ornament, glass color, atmosphere, and final line accents. Use shape or vector tools to create repeated window bays and facade bands, then vary opacity or masks so the repetition does not look sterile. A textured brush set to low opacity can suggest brick and terra cotta, while a clipping mask keeps texture inside each architectural region. For flat Midwestern illumination, use a broad low-opacity layer in warm cream for light and a cool blue-gray layer for shadow, avoiding excessive bloom, lens flare, or photorealistic reflections.

Common Mistakes

FAQ