Playing the entire 100-year campaign takes about 40 hours. At this point, the year stays 2030 and never goes any higher, although the game can continue indefinitely.

If the player remains in business until 2030, the game announces that they have won, allows them to post their name on the 'hall of fame' and then continues. These require a separate track system from railroads. In the game year 1999, monorails become available. Similarly, in the beginning there are only steam engines, but later diesel and electric engines are introduced. Later, they are replaced by red and green traffic-light signals. For example, railroad signals which allow more than one train to use a section of track are initially semaphores. The game features a progression of technology: in any particular year of the game generally only contemporary types of technology are available. As the user plays the game and earns revenues, they have the choice of expanding service along existing routes, or expanding their transportation network. The player starts out by borrowing money to finance construction of transport facilities, and is charged interest until the loan is repaid. The game begins in 1930, and ends in 2030. A station with high ratings may attract more goods. The player's company and the individual stations each have ratings that depend largely on their efficiency at moving goods from one stations to the other. One transport route can utilize several different forms of transport, e.g. To start building a transport empire, the player must construct transport routes, consisting of stations near industries or towns, and in the case of trains or road vehicles, near physical routes.

A fan-made game engine recreation OpenTTD is also available.

A version for Android and iOS was released on 3 October 2013 based on the sequel, Chris Sawyer's Locomotion. Transport Tycoon Deluxe is an expanded and improved version of the original game, released in 1995. It is a business simulation game, presented in an isometric view in 2D with graphics by Simon Foster, in which the player acts as an entrepreneur in control of a transport company, and can compete against rival companies to make as much profit as possible by transporting passengers and various goods by road, rail, sea and air. Transport Tycoon is a city-based pixel video game designed and programmed by Chris Sawyer, and published by MicroProse on 15 November 1994 for DOS.

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