The area has been populated since the Stone Age. During the Roman period, it was a center of iron industry. The name Crawley probably originates from 'craw leah', i.e. 'crow infested clearing', and dates back to Saxon times. The settlement was mentioned in Domesday Book, a survey of all England made at the order of William the Conqueror in 1086. The right to hold a weekly market was granted by charter in 1203.

Lying about 40 kilometres south of London, during World War II Crawley was considered far enough to be safe, and a number of children and businesses were evacuated there. Indeed, the town saw only two serious German air raids, and suffered little damage.

After World War II, Crawley was included in the New Town social experiment under the New Towns Act of 1946. Effectively, the "new towns" were developed to house the numerous people who had lost their homes during the war. They had a car-oriented layout, many roundabouts, a grid-based road system, much the opposite to the maze of narrow winding streets that are the heritage of older towns. Unlike old cities, they were built according to plan. The flip side of the coin is that they often lack atmosphere (of which Crawley is also accused), and often serve as 'dormitories' from which people commute to work daily. Crawley expanded rapidly during the 1950s and the 1960s, in the 1980s it boasted the lowest unemployment rate in the UK. More recently, however, it acquired the reputation of a place where menial and unskilled labour is in the greatest demand, and life is too expensive.

Gatwick Airport is one of the principal employers in the area. In 1890, a race course was built on the site of a manor called Gatwick near Crawley. For several years, the Grand National, Britain's biggest betting horse race, was held there. From 1930, the Surrey Aero Club started flying from Gatwick, and in 1933 an investor purchased the race course and transformed it into an airport. Since World War II, Gatwick underwent several renovations and extensions, and although it has a single runway, it is today Britain's second largest and second busiest airport after Heathrow, handling over 30 million passengers flying to over 200 destinations a year. The airport has two terminals, and a subway was built to connect it with the Gatwick railway station, so that passengers may travel directly from the airport to Victoria Station in London.