SimAirline.net has its origins in Transit International Airways, one of the first virtual airlines. Aaron Robinson joined TIA, which was already becoming inactive in 1999, and took over the management of the Washington hub later that year to prevent it from closing. With no other airlines of interest, Robinson and John Krahnert, the sole remaining pilot from Robinson's TIA hub, decided to jointly create several new virtual airlines in March 2000. The first two, Virgin International Airways (now Virgin Virtual) and Midway Virtual, opened the following month. Virgin was the first virtual airline to incorporate the operations of multiple airlines in it, and the first flight, Midway's Raleigh/Durham to Columbus, was operated on 22 April. Both virtual airlines started well, and Virtual US Airways opened soon thereafter.

United Airlines announced that it would merge with US Airways in May, but it was decided that Virtual US Airways would remain open regardless of real-life events. US Airways contacted Robinson on 20 August 2000, when Virtual US Airways had already become the largest US Airways-based VA, and ordered it to close. US Airways' objections were fought and eventually accepted the following year. To fill the large gap left by the closing, Robinson (Krahnert had departed) opened Continental-Northwest Virtual Airlines in June 2001. A loose association was formed with both Midway and Virgin. Pilot rosters were eventually unified because many pilots wished to fly for more than one airline, making us the first group of virtual airlines to have a unified roster and management (although still no overall organization name).

In August 2001, the real Midway declared bankruptcy and decided to cease operations on September 12. With only a handful of Midway flights flown following this announcement, Midway Virtual Airlines was forced to close at the end of October.

With the success of Continental-Northwest thus far, Robinson looked into expanding the concept with a similar European partnership, based on Swissair and Sabena. The decision was finalized when both airlines announced they would be closing. The organization operated under several names, the first of which was Swissair-Sabena Virtual Airlines.

Following the popularity of the existing three virtual airlines, Continental-Northwest rebranded itself as the Continental-KLM-Northwest Virtual Group in August 2002. This expansion added the operations of Alaska, Hawaiian, and KLM, all partners with both Continental and Northwest. Continental-KLM-Northwest and Swissair-Sabena later broke up into seven separate virtual airlines in January 2003, mainly to increase the marketing abilities of each.

In February 2002, Robinson received a generous offer from a U.K.-based web hosting company, now known as Icarus Solutions. The offer was for a free domain name and web hosting without cost, provided we included their banner ads at the bottom of each main page. SimAirline.net owes its name to the Wil Wright line of "Sim" games, the most famous of which is the SimCity line. SimAirline.net was settled on as a strong name. This secured our position as the first unified virtual airline organization in the world. In early 2003, Delta Virtual opened after the announcement of Delta's alliance with Continental and Northwest. Delta has succeeded Continental as our most popular virtual airline for all but two months since.

We had long been considering a Concorde-based virtual airline, and the announcement of Concorde's retirement provided the right time to do so. Concorde Virtual opened in June after considerable delays in development, the first virtual airline to be based on the scheduled services of one aircraft. In July we opened ANA Virtual, our first Asian virtual airline. Midway Virtual Airlines also reopened in December. Soon thereafter, all virtual airline names were shortened to just the airline name and Virtual for standardization, except for Virgin.

Our 2004 Operations Plan was released in January 2004, outlining eight new VAs we would add, provided pilot monthly goals were met. The first of the 2004 expansion class, Air Tahiti Nui Virtual, opened in March. Copa Virtual followed in May, and South African Virtual and Emirates Virtual each of the next two months. All four of these opened in new regions for SimAirline.net. Alitalia Virtual and Korean Air Virtual opened in September and October, respectively. Air Canada Virtual opened in December. The 2005 expansion class (Icelandair, AOM, Air Berlin, Varig, Thai, Pan American) was decided during the summer of 2004, with goals of expanding in France, Germany, South America, and Southeast Asia, then-weak areas. 2005 saw the opening of Virtual British Airways (from 2004), Virtual Icelandair, AOM Virtual, and Air Berlin Virtual. SimAirline.net also launched a new website design in June 2005, and a new pilot roster system in April 2006. Varig Virtual, Thai Virtual, and Pan American Virtual opened in 2006.

SimAirline.net unveiled a revised logo in September 2006 by adding a background featuring set of pilot's wings with a globe at the center. The revised logo featured the traditional SimAirline.net font and slogan, but with the addition of the pilot's wings, representing our members, and the globe, representing our global options.

In 2007, Frontier Virtual and Hong Kong Virtual also opened, but Air Berlin Virtual was asked to close by its real-life counterpart. 2007 also saw the long-running Message from Aaron replaced by Latitude, a monthly in-flight magazine. This in turn was succeeded the following year by Viewpoint, a regularly updated web journal. 

We plan to conclude virtual airline expansion by adding virtual airlines based on Aeroflot, Aeromexico, China Southern, and Jet Airways. Following Air Berlin's request that we close our virtual airline in January 2007, plans for a replacement virtual airline in Germany following the above virtual airlines began. We have decided to cap expansion at thirty-two virtual airlines.

SimAirline.net has a proud history of innovation, being the first to offer multiple airlines within one virtual airline, the first to operate a unified virtual airline organization, the first to operate a virtual airline based on all the scheduled services of a single aircraft type, and the first to offer a web journal. Today, SimAirline.net has over 600 pilots from 50 countries who together fly nearly 3000 flights a month. Through the end of 2008, SimAirline.net has received 23,038 applications and 159,734 PIREPs.