Flea market with vinyl records in the foreground

Neighborhood News: Maxwell Street Market is Chicago’s Chicago’s original flea market

Flea market with vinyl records in the foreground

The Maxwell Street Market has been a Chicago tradition for more than a century. It not only promotes entrepreneurship, but also provides critically important opportunities for small businesses including craftspeople, artists, farmers, restaurateurs and resellers.” 

Mayor Brandon Johnson, in a statement earlier this year

For 112 years, many generations of Chicagoans young and old, immigrant and native-born, have flocked to the Maxwell Street Market, Maxwell Street between South Halsted Streetand S. Union Avenue, and on S. Union Avenue between W. Rochford Street and W. Liberty Street for great deals, community pride, and entertainment. Their final three dates in 2024 are Sunday, September 1, September 29, and October 27, from 9am-2pm. Admission is free.

In the beginning…

According to the City of Chicago website, Maxwell Street first appeared on a Chicago map in 1847. The street was named after Philip Maxwell (1799 – 1859), an Army surgeon who went on to become the State of Treasurer of Illinois.

As immigrants came into Chicago in the late 19th and early 20th Century in need of jobs and quick cash, fledgling entrepreneurs came to Maxwell Street to earn their livelihood. According to the City of Chicago website, in an era of civil unrest and political change, Maxwell Street Market thrived as a multicultural phenomenon and was even called the “Ellis Island of the Midwest”

According to Wikipedia sources, these early entrepreneurs sold everything from clothes, to produce, to cars, appliances, and tools, officially recognized by the City of Chicago in October 1912. 

It became an economic hub for poor people looking to get ahead. As the Wikipedia sources noted, “merchandise was often considered to have originated from hijacked or pirated railcars/railyards and transport rigs for quick resale and dissemination of articles. Few questions were asked about the origin of a vendor’s items for sale, particularly if the price was right.”

Impact of Maxwell Street Market 

Maxwell Street Market represented a fundamental change in American retail and economic history. As Wikipedia sources note, the market was a response to and rejection of stand-alone retail establishments and their price structures. This microcosm of commerce recognized the availability and influx of Asian and world imports and markets (Taiwan, Japan, China, Mexico) priced dramatically lower than American produced goods. Wholesalers lined Roosevelt Road with goods from all over the world; savvy vendors would buy from them to resell on the market at a profit, usually at a 100% markup. The resulting price(s) fell well below goods available elsewhere, due to low overhead. The market also responded to the power of immigrants and minorities; they could take their cash where they were welcome, accepted, and could shop.

Originating on Maxwell Street…

Maxwell Street is where the Maxwell Street Polish sausage sandwich originated. Word is that it was invented by Jimmy Stefanovic, a Macedonian immigrant, who took over his aunt and uncle’s hot dog stand in 1939 (now called Jim’s Original) located at Maxwell and Halsted in Chicago’s old Maxwell Street market district.

The direct-sales entrepreneur Ron Popeil began his career as a street vendor at the Maxwell Street Market. (think Veg-O-Matic, Chop-O-Matic, etc )

The clarinetist and band leader Benny Goodman was born in 1909 near the Maxwell Street neighborhood and spent most of his youth there.

Singing the Blues on Maxwell Street 

The streets were Initially filled with Klezmer music, brought from Eastern Europe by Jewish immigrants. As the neighborhood changed, so did the music. When economic decline in the American South after World War I caused many Delta Blues and Jazz musicians – notably Louis Armstrong – to migrate north to Chicago. they brought with them outdoor music.

But Wikipedia sources tell the story of an unexpected dilemma arose when the early blues musicians began playing outside on Maxwell Street—they realized they needed either a louder than standard Resonator guitar (e.g., Arvella Gray) or amplifiers and electrical instruments (e.g., Jim Brewer) in order to be heard. Over several decades, the use of these new instruments, and the interaction between established city musicians such as Big Bill Broonzy and new arrivals from the South, produced a new musical genre—electrified, urban blues, later coined, “Chicago Blues.” The last blues performances on Maxwell Street occurred in 1999–2000, on a bandstand erected by Frank “Little Sonny” Scott, Jr., near the northeast corner of Maxwell and Halsted Streets.

Revitalized in 2024

After several decades of changing addresses due to the expansions of the University of Illinois-Chicago in 1994 and other urban expansion, in 2024, the market returned to its original location in 2024. Six market days were scheduled, taking place on the last Sunday of each month through October 27.

Visitors to the Maxwell Street Market will experience an eclectic mix of foods and finds—including handmade crafts, resale housewares, clothing, and much more. This year’s edition features live entertainment and programming from cultural partners, and will incorporate nearby businesses and restaurants including several “Maxwell Street originals” with longstanding ties to the neighborhood, including Express Grill, Hashbrowns, Jim’s Original Hot Dog, Lalo’s Mexican Restaurant and Bar Louie. For more information, click here. 

Alison Moran-Powers and Dean’s Team Chicago