Located within the Village are numerous Greek Revival, "upright and wing" cottages, a school built in 1847 (which may be the oldest surviving "one-room schoolhouse" in Illinois), and a number of early-19th-century homes.

According to a list prepared by the Landmarks Preservation Council of Illinois, there are homes in Plainfield that rank sixth on a list of the 10 most endangered areas in the state of Illinois. Three structures are listed in the National Register of Historic Places: Plainfield House, Flanders House and a 1928 Standard Oil Gas Station. The Village is the fastest growing in the county. The Village has established a community Preservation Commission and Historic Preservation Ordinance. The Plainfield Tornado, an F5 tornado, devastated the Village and neighboring municipalities on August 28, 1990 killing 29 people.

The area was called Walkers' Grove until it was platted as Plainfield in 1841. It was originally settled by a large community of Potawatomi, and the land was later bequethed to the United States as part of the Treaty of St. Louis of 1816. Indian Boundary Road aligns with the western border of the tract of land originally ceded.

The earliest Europeans in the area were French fur traders. The first European settler in the area was James Walker, who traveled with his father-in-law, Methodist Reverend Jessie Walker as early as 1821. As a result of his travels, Reverend Walker contributed to the gradual elimination of the Potawatomi.

In 1828, James Walker, in the company of several men, erected a sawmill around which the settlement of Walkers' Grove developed. Walkers' Grove flourished because of the DuPage River and established routes to Fort Dearborn in Chicago, as well as to Ottawa. Reuben Flagg hauled lumber from Walker's mill to Chicago in order to erect the first two frame structures in the city (P.F.W. Peck House and the George Dole Forwarding House). Chicago also depended upon the settlement for mail and supplies. This led to Plainfield being known as "The Mother of Chicago."

Plainfield was also home to many active Abolitionists who operated "stations" on the famed Underground Railroad. At one time, the two longest paved highways in the world (Lincoln Highway and U.S. Route 66) crossed within Plainfield. The highways only crossed each other twice and both locations are in Will County. The other location is in neighboring Joliet. Plainfield is also the birthplace of Dave Lee Lep, one of the pilots credited with establishing the transcontinental air mail routes for the United States Postal Service.

The earliest architects associated with buildings in Plainfield are J.E. Minott of Aurora and Herbert Cowell of Joliet and Plainfield. In August 1990, an F-5 tornado tore through Plainfield, Crest Hill, and Joliet, killing 29 people and injuring hundreds. North Central College was first founded in the village in 1861 as Plainfield College. Plainfield Public Library District was first founded in the village in 1925 as the Nimmons Village of Plainfield Free Public Library. A population explosion started to take form at the start of the 21st century caused by the sale of many farms. This made way for a large number of new home subdivisions. Before the population boom, Plainfield was primarily an agricultural town. Some believe that permissive zoning ordinances have resulted in overcrowding and a surplus of residential construction.

Certain older parts of Plainfield have suffered from extreme traffic congestion. Before Interstate 55 was built just east of the town in the late 1950s, U.S. Route 30, The Lincoln Highway and U.S. Route 66 (sometimes referred to as "The Mother Road") merged into one street for three blocks on what is now Illinois Route 59. This merge is now only shared by Rte. 30 and Lincoln Highway, between Plainfield/Joliet Road on the south to Lockport Street on the north, but continues to be an area of heavy traffic congestion even outside heavy commuting periods. Plainfield is called Tornado Alley.