The community area contains the oldest extant building in Chicago, the Noble–Seymour–Crippen House, built in 1833 and greatly expanded in 1868.

[6] William Howard Taft High School, best known as the inspiration for the musical Grease, was completed in 1939 with major additions made in 1959 and 1974.

The first inhabitant of European descent in the area was Mark Noble, who arrived in 1833 and constructed a house that is still standing as of 2024, the oldest in the Chicago city limits.

[3][4] English farmers were the main group in the 1830s, although they would later be supplanted by Germans and to a lesser extent Poles and Scandinavians.

[4] In 1853 the Illinois and Wisconsin Railroad, which would eventually become the Chicago and North Western Railway and is currently Metra's Union Pacific / Northwest Line, laid tracks in the area, and in 1868 the Norwood Land and Building Association was formed and purchased the land.

[3][4] A hotel was constructed shortly thereafter in an attempt to lure tourists from Chicago, although it was ultimately unsuccessful.

[8] The first liquor store in the area in 50 years opened in 2016, without controversy about its existence but with such restrictions on its operation as early closing hours and a price minimum of $5.99.

Rufus M. Hitch Public School, located on North McVicker Avenue, is in the area and zoned to as well.

Opposite of the neighborhood's southern border at Gunnison Street is the suburb of Harwood Heights and an unincorporated area housing Ridgemoor Country Club.

Many of the city's police officers live in Big Oaks, and in recent years the area has seen an increase in the number of Polish immigrants.

The area is home to Oriole Park, which is located in the center of the neighborhood south of Bryn Mawr Avenue.

Union Ridge, one of the highest points of Cook County,[3] is bounded by Bryn Mawr, Foster, Nagle, and Harlem Avenues.

[15] In the Cook County Board of Commissioners the large majority of the area is in the 9th district, represented by Republican Peter N. Silvestri, while the eastern parts of Norwood Park East, Union Ridge, and Big Oaks are in the 10th district, represented by Democrat Bridget Gainer.

Norwood Park has supported the Democratic nominee for President in the past two presidential elections.

A 2011 reproduction of the original Grease musical by American Theater Company in Chicago revisited Norwood Park's influence on the production.