Will Southwest fly to Canada? Canada is international destination that Southwest has said is on its radar.

As recently as April 2021, Southwest CEO Gary Kelly said the airline had identified five to seven really nice markets, according to an article on Business Insider.

Southwest Airlines Canada
Credit Travel Alberta

At the company’s annual shareholders meeting in 2018, CEO Gary Kelly said the airline is interested in launching services to Canada out of Baltimore, according to ch-aviation.

The article attributed Kelly as saying Southwest may sign an agreement with another carrier to serve transatlantic routes from the Baltimore airport, which would make sense as a connecting point to Europe (Southwest to Europe?! Yes please!).

He did say, however, according to the Orlando Sentinel, that Hawaii is the airline’s focus first.

That has continued to be the case in 2021 with Kelly noting that they might not currently have enough aircraft to add Canada and that another challenge is updating its booking system to accept Canadian dollars, again according to Business Insider.

Currently, you can get close to Canada by flying Southwest to:

  • Detroit
  • Buffalo, New York
  • Bellingham, Washington

The Orlando article said Kelly explained that “Southwest is eyeing a host of expansion opportunities within the next 25 years, with as many as 50 additional North and South American route expansions under consideration.”

In 2020 and 2021, Southwest added numerous destinations to its line-up, including:

  • Bozeman, Montana
  • Telluride, Colorado
  • Steamboat Springs, Colorado
  • Sarasota, Florida
  • Colorado Springs, Colorado
  • Santa Barbara, California
  • Fresno, California
  • Jackson, Mississippi

Where would you like to see Southwest fly?


  • Lyn Mettler

    Lyn Mettler is a longtime travel writer for US News & World Report, USA Today 10Best and The TODAY Show who created Families Fly Free, a program which teaches families her simple system to use travel rewards to fly for free.

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