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Its name came from Anglo-Saxon Cissan dun = "hill belonging to [a man named] Cissa".

Chessington appears in the Domesday Book as Cisedune and Cisendone. It was held partly by Robert de Wateville and partly by Milo (Miles) Crispin. Its Domesday assets were: 1½ hides; part of a mill worth 2s, 4 ploughs, woodland worth 30 hogs.

The mansion at Chessington World of Adventures, known today as the Burnt Stub, was originally built in 1348. In the English Civil War it became a royalist stronghold and was razed to the ground by Oliver Cromwell's Parliamentary forces, giving it its modern name. The site became an inn and was then rebuilt on a grander scale from the 18th century by the Vere Barker family in a Neo-Gothic Victorian style. The grounds were turned into a zoo in 1931 by Reginald Goddard. Chessington Zoo became part of the Tussauds Group in 1978 and is now operated as a theme park. Burnt Stub had no public access until 2003 when it became an attraction called Hocus Pocus Hall.

Chessington Hall has a place in 18th-century literary history, as home of Samuel Crisp, a failed playwright and close friend of Fanny Burney. Chessington Road Recreation Ground was purchased on 16 October 1930.

At 207 Hook Road is a Blue plaque commemorating the author Enid Blyton who lived at the address between 1920 and 1924.

The former RAF Chessington Hospital, demolished in the 1990s, first opened as RAF Hook around 1938 as a regional barrage balloon depot and was operated by RAF Balloon Command. It became a vital part of Britain's defence against the Luftwaffe in World War II and originally featured a number of large barrage balloon sheds as well as extensive garages and workshops for the station's support vehicles.

Chessington houses one of the Europe's leading theme park resorts Chessington World of Adventures. This includes a zoo, a theme park, an aquarium and two four star hotels - the Safari Hotel and Azteca Hotel. In the grounds of the resort lies the historic Burnt Stub Mansion.

Chessington Garden Centre is located in the south of the area near Malden Rushett.

Chessington offers a range of countryside activities with many open spaces including the "Chessington Countryside Walk" in the London Green Belt. Chessington Wood, in the south of the area, contains the source of the Bonesgate Stream, a tributary of the Hogsmill River, in turn a tributary of the River Thames.