The mansion at Chessington World of Adventures Resort known today as the Burnt Stub was originally built in 1348, in Chessington, Surrey. In the English Civil War it became a royalist stronghold, and Oliver Cromwell's Parliamentary forces razed it to the ground. The Burnt Stub site was rebuilt as an inn, until the 18th century, when the Vere Barker family rebuilt it in neo-gothic Victorian style.

The resort has its roots in Chessington Zoo, which opened in 1931; it was started by Reginald Stuart Goddard, who had bought the estate to showcase his private collection of animals. It was once the largest private zoo in England. After Goddard died in 1946, the Pearson Publishing Company took over the zoo and managed it until 1978, when The Tussauds Group, a subsidiary of the Pearson Group, took control.

In 1984, due to the zoo's declining attendance, Tussauds's commissioned John Wardley to come up with plans to revitalize the park. Wardley had a huge influence on the rides being created at both Chessington and its sister parks Thorpe Park and Alton Towers. The decision was made to open a theme park to complement the zoo, and so Chessington World of Adventures was born. On 7 July 1987 Chessington World of Adventures opened to the public in a ceremony including Prince Edward. The park was built on a relatively small budget of around £12 million, to test the still-emerging theme park market.

In its first year, the park opened with the roller coaster Runaway Mine Train, the log flume Dragon River, the monorail Safari Skyway, the dark ride The 5th Dimension, and the Chessington Railroad as the main attractions (all supplied by the German ride manufacturer Heinrich Mack GmbH & Co). Smuggler's Galleon (a swinging ride) reached heights of 20 meters; it was later renamed Black Buccaneer.

The new park development adopted a pay-once price structure as opposed to the fairground's former pay-per-ride format. Other support rides were also opened and the park opened five themed areas: Calamity Canyon, Mystic East, Market Square, Toy Town and Circus World.

The 1990 season expanded Chessington with the opening of the Transylvania area, featuring The Vampire (opening and still operating as the only suspended rollercoaster outside of America) and Prof. Burp's Bubble Works. Both of these major rides had a significant and positive impact on the park's popularity. By this time Smugglers' Galleon and the Smugglers' Cove area had been created.

The 1995 season arrived with Rameses Revenge, the park's first inverting ride. Rameses Revenge was new in the Forbidden Kingdom area; an area which had opened the previous year in conjunction with the Terror Tomb dark ride. Also new for 1995 was Seastorm in Pirates' Cove, and the Carousel, located next to the explorer gate. By 1997, the park had a maximum capacity of 15,000 guests.

In 1999, Chessington opened the hardcore thrill ride Samurai in the Mystic East. 1999 also saw the rename of Calamity Canyon into Mexicana, following the opening of Rattlesnake the year before. Beanoland, bringing two new rides to the park: Billy's Whizzer and Rodger the Dodger's Dodgems was built in 2000 on the former site of Circus World

On 22 May 2007, The Tussauds Group was taken over by Merlin Entertainments Ltd, which owns other brands such as Sea Life Centres. Besides Chessington, Merlin also purchased Alton Towers, the nearby Thorpe Park, and Madame Tussauds, which made Merlin the second largest entertainment operator in the world in terms of attendance numbers, behind Disney. As Chessington World of Adventures and Thorpe Park are located within 20 miles of each other, Merlin Entertainments has made efforts to market the two parks to different age groups: Thorpe Park caters to teenagers and young adults, while Chessington World of Adventures Resort is for families and people of all ages. In June 2007, the park opened the Safari Hotel next to Chessington Zoo, themed to a safari lodge. 2008 saw the opening of the Chessington Sea Life Centre.

Also in 2010, the Wanyama reserve was opened, giving the Africa-themed Safari hotel guests a view of animals. The Wild Asia area was also added, with its KOBRA ride. In 2011 the Ocean Tunnel and surrounding rooms in the Sea Life Centre were re-themed to Azteca. In 2012 a new land themed to Africa replaced ToyTown. In 2013, Chessington introduced Zufari: Ride Into Africa, with visitors touring the area in a safari truck. In the same year, the annual Halloween Hocus Pocus event included a new attraction, The Mystery of Hocus Pocus Hall, featuring projection-mapped visual effects.

In 2014, "nearly £15 million" was invested in the resort as the whole, with a new wing built next to the Safari Hotel, advertised as a second standalone hotel, named "Azteca Hotel". The Safari Hotel also received a second pool. Theme park developments for the year included the refurbishment of the Runaway Train roller coaster as Scorpion Express and Amazu Treetop Adventure, a children's raised play area within the zoo. The park's annual Halloween event was rebranded Howl'O'Ween. Over the festive period Chessington launched the new Winter's Tail event, featuring a new seasonal show A Christmas Gift, as well as market stalls and a 60 ft Christmas tree. Attendance rose to 2.05 million guests in 2014, the second highest figure in the park's history, which previously peaked in 1995.

2015 was advertised as "Year of the Penguins", introducing an updated Penguins of Madagascar Live: Operation Cheezy Dibbles show on the Madagascar stage, a rethemed "Jungle Bouncers" as "Penguins of Madagascar Mission: Treetop Hoppers" (now just Treetop Hoppers) and "Penguin Bay", a refurbished enclosure for the Zoo's Humboldt penguins. New Penguins of Madagascar themed suites also opened in the Safari Hotel. 2015 also saw the Chessington Conservation Fund Evening relaunched as "Roar & Explore". The new event features night rides on Zufari: Ride into Africa! as well as child-friendly activities. Chessington's attendance fell in 2015 to 1.65 million. The long-running Safari Skyway monorail closed midway through the year, after 29 years of service.

Little was changed during the 2016 season, a small live show named Pandamonium opened near the zoo, a Go Ape high ropes course opened, and Trail of the Kings received some new decoration. Explorer Glamping was also introduced over the summer months, launching on 27 May. Tomb Blaster was refurbished with all LED UV lighting and new laser gun system.

In 2017, The Gruffalo River Ride Adventure opened, replacing Bubbleworks, as well as the original Carousel being replaced with a newer, themed carousel named "The Chessington Adventure Tree".

In 2018, the Ferris wheel Peeking Heights was removed and the Mystic East area rethemed into Land of the Tiger, with three new tiger enclosures, four tigers from Kolmården Wildlife Park, and a new theme for Dragon Falls, with its new name Tiger Rock.

In 2019, they rethemed their old 3D walkthrough attraction, Hocus Pocus Hall, into another one of Julia Donaldson's creations, Room on the Broom – A Magical Journey. Halfway through the season, Chessington announced that their swinging boat ride, Black Buccaneer, would not open for 2019. In October, Chessington announced that Rameses Revenge would close on 3 November.

2020 saw the opening of a new area called The Rainforest. The area included 3 new attractions, the first of which, a kids track ride called Jungle Rangers. The second is a relocated mini log flume from Weymouth Sealife called River Rafts. The third is the pre existing treetop hoppers which retained its name and was refurbished. The Flying Jumbos Ride was also relocated and rethemed into Elmers Flying Jumbos based on the children's book.

2021 saw a new family drop tower 'Croc Drop' open, themed to the Egyptian god Sobek, replacing Rameses Revenge. Blue Barnacle also opened to replace the now defunct Black Buccaneer swinging pirate ship.

2022 saw a retheme and refresh of the Pirates' Cove themed area, to Shipwreck Coast, with the addition of two new rides. These are 'Barrel Bail Out', a Watermania ride and 'Trawler Trouble', a Rockin' Tug relocated from Thorpe Park. Seastorm also reopened following an extensive refurbishment. On top of this there was general park wide refurbishments and touch ups, with some significant work in Wild Asia and Adventure Point as well as a new Explorer Gate entrance, in preparation for World of Jumanji in 2023. Jungle Bus in Wild Asia left the Resort for the 2022 season. It was replaced for 2023. 2022 was a year of 'eventures' with a new carnival event 'Mardi Grrra!' running from 27 May – 26 June.

2023 has been a major year for the resort, with the opening of a new land on 15 May, 'World of Jumanji'. The new area features a B&M Shuttle Launched Wing coaster, and two SBF Visa Group attractions. There is tropical planting around the area and a huge theming piece; the 'Jaguar Shrine' from the films. The park are also building a Safari Lodge village on the Wanyama Reserve for the 2023 season.