The Free Trade Agreement (FTA) between Canada and the United States established the basis for the subsequent creation of the North American Free Trade Area (NAFTA). Despite the economic and geographic differences, Chile can learn from the Canadian experience, as there are similarities in their positions for negotiating a free trade agreement with the United States. Thus, this paper analyzes the background of the Canadian decision to seek an agreement of this type, the essential points and objectives of its negotiators and the results, in addition to the effects of the first time of operation. Finally, the main lessons for Chile are mentioned: obtaining an acceptable mechanism for the solution of commercial disputes; take advantage of NAFTA's advent clause instead of bilaterally attempting a new agreement and seeking support within the United States.