FEATURE image: 946 N. Sheridan Road, Waukegan, Illinois 1876.

Waukegan’s surviving architecture serves as a visual record of the city’s transformation from frontier trading post to prosperous Great Lakes industrial center, preserving nearly a century of changing architectural tastes and civic ambitions.

Text & photographs by author.

INTRODUCTION

Waukegan, Illinois, is an historic community on Lake Michigan about 40 miles north of downtown Chicago. It is one of the oldest settlements in Illinois. The site of the city was visited by French explorers Louis Jolliet (1645-1700) and Père Jacques Marquette, S.J. (1637-1675) in 1673 where Waukegan began as a French trading post and Potawatomie village.

Inside the Kiva (c.1905-1912), oil on canvas. 20 in. x 30.25 in., Kate Cory (1861-1958), Waukegan Historical Society. Waukegan photographer, sculptor, painter and muralist Kate Cory moved to Newark, New Jersey, with her family as a child. Between 1905 and 1912 she lived among the Hopi of the Oraibi Mesa in Arizona where this painting was made.  Public Domain.

Waukegan’s origins as “Little Fort.”

“Little Fort” was the first name for the environs of Waukegan. It started around 1700 as a log building overlooking the Waukegan River on its southwestern shore as it drained into Lake Michigan. This point marked the portage from the Lake to the Des Plaines River as it traveled west. The state of Illinois was established in 1818. Over the next quarter century, the Illinois volunteer army fought local native American tribes and forced them to sign treaties and migrate west of the Mississippi. The Potawatomie left Waukegan by 1829 as they ceded their land in this area and throughout northeastern Illinois to the U.S. Government. The 1830s brought vast changes to the area with opportunities for development. In addition to the land transfer, the building of the Erie Canal in 1830 brought boatloads of settlers from New England and New York State into the Illinois and the Midwest region.

Along with other communities which developed on Chicago portage routes, the history of Waukegan’s founding and development shares a similar time frame as well as personalities and activities. In 1835 Thomas Jenkins was the first settler at “Little Fort.” Jenkins was followed in quick succession by other enterprising and hard-working New Englanders who settled much of northern Illinois in the 1830s which was the edge of the Western wilderness. Like Marquette and Jolliet in the 17^th century, these newcomers recognized the potential monumental impact that access to Lake Michigan had for transport of goods in and out of the region and what that commercial activity and subsequent settlement would have on the surrounding real estate. As more people arrived, the creation of a village emerged. The area was platted and streets designated, and in a contested election in 1841, “Little Fort,” became the governmental center for a recently formed Lake County.

Little Fort Becomes Waukegan

Between 1844 and 1846 the town’s population multiplied from 150 to 750 persons. In 1849 the community changed its name from “Little Fort” to Waukegan. By 1859, when the town was incorporated as a city, Waukegan boasted a population of 2,500 people. Chicago, by comparison, had a population of 112,172 denizens in the 1860 census. Waukegan is an English alliteration that closely approximated the word for “fort” or “trading post” in the Algonquin language. In the 2020 census Waukegan reported a population of 89,321 people.

Growing population in the port city. Coming of the railroad

Waukegan had a natural deep harbor and was a port city. This feature attracted merchants and farmers who could readily ship their goods, produce, and grain from Lake and McHenry County businesses and farms to Chicago –- and, from that point, to the Midwest and the world. Waukegan soon became one of the busiest ports on the lake. When the railroad came to Waukegan in 1855 (today’s Chicago and North Western Railway), it stimulated interest in Waukegan as a manufacturing town that included ship and wagon building, flour milling, sheep raising, pork packing, beer brewing and dairy farming (Hawthorne-Melody Farms). The railroads made it feasible for the establishment of larger industries which appeared in Waukegan at the end of the 19^th century such as U.S. Sugar Refinery, Washburn and Moen Wire Mill (U.S. Steel Corporation), U.S. Starch Works, and Thomas Brass and Iron Works, among others. This mercantile and agricultural activity generated sufficient wealth for its citizens to build big houses along Waukegan’s main streets. These residences expressed the current tastes in residential styles from Greek revival and Italianate styles to the Victorian and Prairie School.

1890-1930: Population boom fueled by immigration

Between 1890 and 1930 Waukegan experienced a population boom fueled by European immigrants and, in the 1920’s, Black Americans during the Great Migration. Waukegan thrived though by the end of the 20^th century, the city suffered from an exodus of its population to farther west suburbs. This was accompanied by a shuttering of industries as management sought cheaper labor in other countries. At the same time, Waukegan was welcoming a new influx of immigrants from Latin America.

Famous residents

A few of Waukegan’s most famous residents in history include comedian Jack Benny (1894-1974), science fiction writer Ray Bradbury (1920-2012), World War II combat photographer under Colonel Darryl F. Zanuck (Twentieth Century Fox) Albert Klein, the aforementioned fine artist Kate Cory and NFL quarterback for the Cleveland Browns Otto Graham (1921-2003).

When he became famous, Jack Benny never forgot his hometown of Waukegan.

Science Fiction writer Ray Bradbury said he had a sign over his typewriter for 25 years as advice to himself and other writers: “DON’T THINK.”

When Otto Graham played for the Cleveland Browns the team played in 10 consecutive title games, 4 all-American Conference and 3 NFL championships. In Waukegan, Otto Graham’s father was a music teacher who taught Jack Benny to play the violin.

THE HOUSES:

408 N. Sheridan Road, 1875. Built in the Italianate style in 1875. The set of four symmetrical bay windows on the first and second floors have 12 tall thin windows. The moldings have scroll cut, incised, and cut out brackets with heavy decorative surrounds with keystones. In the center above the canopied main entrance are a second floor and gable windows with heavy shoulders for its surrounds. Above the gable window is punched out, playfully decorative bargeboard. The two story porch to the south (left) while integrated to the Italianate building is a later turn-of-the-century addition.

414 N. Sheridan Road, 1847. The strict Greek Revival-style modest building dates from 1847. Built by John H. Swartout, the frame house has a portico with a perfect classical pediment with Doric columns holding up a blank entablature. The façade hosts three identical openings – two being windows with shouldered moldings and a door with a transom. It is a simple and relatively small building that was in need of repair in 2014 when this photograph was taken by the author.

438 N. Sheridan Road, 1840s. The house was built up around a small 1840s Greek revival Style house. The Italian Villa style with its tall central tower, porch and columns, double brackets under the eaves and pediments above the windows, dates from the middle 1850s. the central door starts with the rope molding around the double doors and ascends to double arched windows on the second and third floors.

438 N. Sheridan Road, 1840s. Same house as above, southern exposure. The tower’s windows are replicated on each side at the same level as the front view.

505 N. Sheridan Road, 1850s. A central tower with a double window and a peaked arched pediment and a steep pitched roof marks this house from the 1850s as Greek Revival style. The door has heavy shoulders for its surrounds.

526 N. Sheridan, late 1840s. A Greek revival style house prevalent in the state of Ohio. The Greek Revival gable has short returns with the second-floor windows extending into the gable area. This is a construction short cut for these upper story rooms. The porch with its octagonal columns and front door entry with its heavily bracketed canopy are later additions although no later than the mid1870s.

619 N. Sheridan Road, 1840s. The present house was built around an earlier house erected in the 1840s. It is in the Victorian Gothic style. There are steep gables for the central tower and dormers. The central doors and windows have simple and neat surrounds.

Detail of same house above, 619 N. Sheridan Road, 1840s.

Waukegan’s historic houses and neighborhoods reveal the story of a city shaped by lake commerce, railroads, industry, immigration, and economic growth, with its architecture preserving the ambitions and cultural aspirations of successive generations from the 1840s through the early twentieth century.

710 N. Sheridan Road, 1872. A restored Second Empire and Italianate Victorian mansion. The frame house features a double door entrance with glass panes and a veranda-like columnar front porch. A square-shaped second-floor porch is above the front entrance in the central section of the house and below its double bracketed cornice and Mansard roof.

Detail of double bracketed cornice of restored 1872 Second Empire and Italianate Victorian mansion at 710 N. Sheridan Road in Waukegan, Illinois.

Waukegan preserves a remarkable range of architectural styles including Greek Revival, Italianate, Italian Villa, Victorian Gothic, Second Empire, and Tudor Revival.

837 N. Sheridan Road, 1858. The front porch and polygonal bay window were added to this late-1850s Italianate brick house more than 60 years later, around 1910.

907 N. Sheridan Road, early 1930s. Made of Lannon stone from Wisconsin, the buff-colored, blocky, sedimentary dolomite rock house is designed in the English Tudor style. It has a slate roof. The tall wide chimney is integrated into the façade of the solid stone wall building flanked by casement windows in gabled wall dormers.

Another view of same house above, 907 N. Sheridan Road, early 1930s. The well-designed monolithic stone and slate fortress was erected during the Great Depression.

Individual houses illustrate changing architectural fashions across nearly a century of development. Waukegan’s built environment reflects both nineteenth-century optimism and twentieth-century prosperity before later industrial decline and demographic change.

946 N. Sheridan Road, 1876. An Italianate house has a central tower with notable openings – a ground floor heavy doorway; above that, a pair of windows under a semi-circular pediment; and finally, at the top, a triplet of windows under a triangle pediment. The second floor carries the semi-circular pediment design across three more of its windows and there are double brackets under the eaves. The porch is likely an early 20^th century addition.

1004 N. Sheridan Road, late 1890s.

Sources:

Bach, Ira J. 1981. A Guide to Chicago’s Historic Suburbs on Wheels and on Foot. Chicago: Swallow Press/Ohio University Press, pp. 97-111.

Encyclopedia of Chicago. n.d. “Waukegan, IL.” Accessed May 3, 2023. http://www.encyclopedia.chicagohistory.org/pages/1328.html.

Waukegan Historical Society. n.d. “Historical Places.” Accessed May 3, 2023. https://www.waukeganhistorical.org/places.

Waukegan, Illinois, City of. n.d. “Demographic Information.” Accessed May 3, 2023. https://www.waukeganil.gov/178/Demographic-Information.

Waukegan, Illinois, City of. n.d. “History of Waukegan.” Accessed May 3, 2023. https://www.waukeganil.gov/181/History-of-Waukegan.

Wikipedia. s.v. “Demographics of Chicago.” Last modified October 3, 2026.https://en.wikipedia.org/wiki/Demographics_of_Chicago.

Wikipedia. s.v. “Otto Graham.” Last modified October 1, 2026.https://en.wikipedia.org/wiki/Otto Graham.

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