JALways was founded as Japan Air Charter on October 5, 1990 and began charter operations with a McDonnell Douglas DC-10 on February 22, 1991. The airline obtained a license to operate scheduled services on July 30, 1999 and operated its first scheduled passenger service on October 1. On the same day, the airline changed its name to JALways. In the fiscal year ended March 31, 1999, JALways, together with its sister airlines within the JAL Group, carried over 32 million passengers and over 1.1 million tons of cargo and mail.
The airline was established on October 5, 1990, as Japan Air Charter Co., Ltd. (JAZ), an 80 percent-owned low-cost charter subsidiary of Japan Airlines (JAL), to operate leisure flights to Asia-Pacific resort destinations from regional airports in Japan; in response to a Ministry of Transport policy. JAZ obtained its aircraft from JAL; its cockpit crews were American contract pilots based in Hawaii and its cabin crews were hired and based in Bangkok, where it operates a cabin crew training centre. JAZ obtained license to operate non-scheduled services on February 22, 1991 and operated its first charter flight from Fukuoka to Honolulu with a McDonnell Douglas DC-10 on July 1. The airline celebrated its 100,000th passenger on July 9, 1993, in a ceremony held in Sendai.
During the 1990s, JAL was hit by the effects of Japan's recession, increased foreign competition and the strengthening of the Japanese Yen, JAZ was given a new role to help reduce costs. The airline obtained the license to operate scheduled services on July 30, 1999 and would operate as a scheduled carrier on a wet-lease basis for JAL. It would operate on high-density low yield tourist routes in the Asia-Pacific region, particularly the Japan–Hawaii services; with a fleet of four McDonnell Douglas DC-10s and five Boeing 747s. On October 1, the airline changed its name to JALways Co., Ltd. and operated its first scheduled passenger service from Tokyo to Kona and Honolulu.
JALways became a wholly owned subsidiary of Japan Airlines on March 9, 2001 through an exchange of shares. The change in ownership enabled JAL to consolidate and improve management and operational efficiency in the JAL Group's international passenger operations, part of the JAL Medium Term Corporate Plan 2000-2002. The airline introduced new uniforms for its cabin crew on April 1, 2005, and retired its last McDonnell Douglas DC-10 on October 31. JALways became an affiliate member of Oneworld on April 1, 2007, together with four of its sister airlines, in the alliance's biggest expansion in its young history.