On November 1, 1996, Kevin Benson, then president and CEO, unveiled a restructuring strategy to improve the profitability of Canadian Airlines International.

The operational restructuring plan was supposed to be phased in over a four-year period, addressing the main issues of cost control, revenue growth, capitalization and fleet renewal.

The plan started off well but with the effects of the 1997 Asian financial crisis, air traffic decreased and Canadian suffered heavy losses on previously profitable trans-Pacific routes.

Canadian Plus was the largest frequent flyer program in Canada with more than 60 airline, hotel, car rental, and financial partners worldwide.

Canadian Airlines' core business strategy focused on building its Vancouver hub into the leading gateway between North America and Asia.

This financial offer evolved from a merger proposal between Canadian Airlines and Air Canada which had been ongoing since early 1999.

Afterwards, American sold its shares in Air Canada as the company decided to change its corporate strategy regarding the Canadian aviation market.

On October 19, 1999, Air Canada, backed by Star Alliance partners Lufthansa, United Airlines and CIBC announced a $930M counter bid to the Onex offer.

On November 5, 1999, a Quebec judge ruled that the Onex takeover was illegal, breaking the law that stipulates that no more than 10 percent of the company can be controlled by a single shareholder.

Onex subsequently withdrew its offer and Air Canada stated it would proceed with the takeover of Canadian Airlines.

On December 4, the board of directors at Canadian Airlines recommended the $92M merger offer from Air Canada to the shareholders.

September 26, 2001 saw an additional 5000 cuts primarily driven from the worldwide impact to the travel sector caused by the 9/11 attacks.

Following the completion of the acquisition, Air Canada controlled over 90% of the domestic share of passengers, and dominated international and US-Canada transborder traffic.

At the time, this fact was widely reported by Canadian media including CBC Venture and Maclean's Magazine.

The website was created by and credited to Grant Fengstad who at the time was leading a strategy to demonstrate that the Internet was going to revolutionize the travel sector.

The livery, known as "Proud Wings", featured a large Canada goose painted at the tail of the aircraft and the airline's name in a new Celeste font.

[citation needed][10] In the 1996 film Homeward Bound 2: Lost in San Francisco, the family is flying to Canada on Canadian Airlines when the pets escape.