Chicago artist puts his stamp on USPS 250th anniversary

The United States Postal Service (USPS)  marked its 250th anniversary, which was July 29,with the release of a commemorative stamp series featuring artwork by Chicago-based cartoonist Chris Ware. The series, released last week, celebrates a quarter-millennium of delivering mail across the nation.

One of the highlights of the series is a special sheet of 20 Forever stamps titled “250 Years of Delivering.” Together, they form a single illustrated scene depicting a Chicago-inspired cityscape and the daily life of a mail carrier, shown across four seasons.

The USPS predates the nation itself, tracing its origins to colonial America and the service of Benjamin Franklin as the country’s first postmaster general. To mark this semi-quincentennial milestone, USPS released two special issues on July 23: a redesigned Benjamin Franklin stamp in a 32-page prestige booklet called Putting a Stamp on the American Experience, and Ware’s storytelling sheet of 20 interconnected stamps, titled 250 Years of Delivering.

A USPS press release describes the pane as a “bird’s-eye view of a bustling town,” where “each stamp follows a mail carrier’s daily route” through all four seasons.

Ware, a Riverside, IL, resident and acclaimed comics artist, co-designed the pane with USPS art director Antonio Alcalá. “I was indeed flattered and honored to be asked to do a stamp,” Ware told The Forest Park Review. “I figured I would either scare off the Post Office with my ideas and/or make something that wasn’t printable. Instead, I was pleasantly surprised to find that everyone working for the USPS was unpretentious, funny, and very agreeable.”

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The artistic narrative follows a mail carrier through her route in a Chicago-inspired urban landscape populated with coffee shops, government buildings, and neighborhood gatherings. The scenes offer a nod to USPS history, from a pony‑express statue to various vehicles and mailboxes. “I was hoping to make something that a letter carrier might happen to see and maybe feel some connection to… their lives seem to be a ‘Groundhog Day’ level of grind and repetition… I wanted to try to honor that,” Ware said.

The “Putting a Stamp on the American Experience” booklet includes a newly modernized version of the original five-cent Franklin stamp from 1847, alongside a modern interpretation of President George Washington from the first 10-cent issue. According to USPS press materials, the commemorative booklet and Ware-designed stamp sheet include pricing and features aimed at stamp collectors.

Despite the festive occasion, consumers continue to voice frustration over recent postage price increases. As of July 13, the price of a Forever stamp rose from 73 to 78 cents, and the whole pane of Ware’s stamps is priced at $15.60. USPS defended the adjustment as necessary to fund its “Delivering for America” modernization plan, which includes infrastructure investment and financial stabilization measures.

At 57, Ware has had a long association with the Chicago art scene and local weekly independent publications, yet he joked in an interview with WBEZ, “Designing a U.S. stamp felt like the kind of thing moms love to brag about, so I said yes.”

These new stamp issues are now available online and at US post offices nationwide, offering collectors and letter‑senders a distinctive tribute to 250 years of American mail delivery.