Cermak was a Czech immigrant credited with creating a diverse Democratic political coalition that included formerly Republican African Americans.

A trip from east to west along Cermak Road traces a historical timeline of the Chicago area, from Yankee industrialists' masonry mansions in the Prairie District on the lakeshore, to mammoth printing presses and manufactories banking the Chicago River and Sanitary Canal, past immigrants' crowded brick housing, schools and churches, along boulevards of temporary middle class success and massive plants that produced twentieth century equipment for the nation, through commercial districts made up of shops and savings banks that boomed in the 1920s.

Further west, a river and forests curtained off the farmland that was eventually developed into asphalt-encircled shopping malls or steel-framed, glass-walled corporate towers.

Transportation evolved from waterborne lake and river vessels to steam powered railroads reaching across the continent and electrified urban systems connecting neighborhoods and towns to super highways overlaying all of the predecessors.

[5] At the southeast corner of Michigan Avenue once sat Prohibition-era mobster Al Capone's headquarters from 1928 until 1932, the Lexington Hotel,[6] which was built in 1892, vacated in 1980, and demolished in 1995.

Michigan Avenue to the north and south is designated the Motor Row District, which commemorates the earliest days of automobile retail showrooms.

[15] Cermak Road now cuts through the north end of the community area Armour Square, heads west under Metra and CTA's Red Line,[16] meets four exit lanes and two entrance lanes of the Dan Ryan and Adlai Stevenson Expressway Expressways, and then intersects with Chinatown's main commercial strip, Wentworth Avenue.

[19] Archer Courts Apartments, 2242 S. Princeton, is a 147 unit subsidized rental building built in 1951 by the CHA and placed into a TIF[20] in the late 1990s.

Cermak Road, a newer axis of Chinatown, obliquely crosses the west-southwest angular artery Archer Avenue, dips to pass through a long chute underneath a viaduct beneath the Midway Airport Orange Line and another rail line just east of Canal Street and enters into a Chicago landmark area designated the Cermak Bridge District,[21] part of the Lower West Side.

The road traverses a Scherzer rolling lift type bridge over the south branch of the Chicago River, past old factories, a cement plant and the Carpenter Training Center, and then under the Dan Ryan Expressway (Interstates 90 and 94) to Halsted Street into the Pilsen neighborhood, named for a city in the present-day Czech Republic.

At the southwest corner of Throop Street (1300W) stands a red brick structure topped with a radio antennae-equipped gothic tower that formerly housed Commonwealth Edison garages and warehouses, then Warshawsky & Sons JC Whitney automobile parts supplier, and most recently subdivided warehouse spaces and indoor futbol (soccer) fields.

On the east side of Wolcott is the Cristo Rey Jesuit High School which took over the site from St. Stephen's Church, a Slovene parish founded in 1898.

The Metra Burlington Northern rail line serves as the north boundary of the Little Village neighborhood as it heads southwest [29] to its terminus in Aurora, Illinois.

The street widens in North Lawndale and is banked by more residential structures, mainly brick two and three flats and corner storefronts in multi-unit buildings.

After crossing Ogden Avenue and Pulaski Road and entering the neighborhood nicknamed K-Town, the westbound and eastbound lanes are divided by a grassy parkway median, causing Cermak to resemble a boulevard before meeting Chicago's western city limits at the Belt Railway [31] viaduct at 4600 West.

From the railroad to the southeast corner of Cermak and Cicero Avenue (Illinois Route 50) was the site, from 1905 until 1983,[32] of the Western Electric Company's famous Hawthorne Works, which at one time employed 45,000 workers.

At the northwest corner with Laramie Avenue (5200W) is a Commonwealth Edison Substation building and yard which also houses Chicago Transit Authority electrical equipment.

At the southwest corner of Oak Park Avenue (6800 West) is the restored American State Bank building, built in 1925 and now home to the Big Hurt Brewhouse restaurant.

Just west of the mortuary, Forest Preserve District of Cook County (FPDCC) picnic groves lie on both sides of the road.