- In 1982, a group of pilots and flight attendants from the defunct Braniff International, helped by businessmen from Minneapolis/St. Paul, established Sun Country Airlines.
- In the early days, the airline had 33 employees and exclusively operated charter flights, starting with the Sioux Falls – Las Vegas route.
- During the remaining part of the 1980s, Sun Country Airlines flew to various destinations, including Oslo, for example, and became a member of the Civil Reserve Air Fleet, flying military charters to Saudi Arabia and Bahrain.
- At the end of 1991, the airline reported record earnings of $9.7 million, doubling its fleet and workforce.
- On the 1st of June, 1999, Sun Country Airlines became a scheduled carrier, but the years to follow were pretty hard, and the airline ceased all activity in December, 2001.
- Pretty soon, a group of investors purchased the airline and flights resumed in early 2002.
- Sun Country Airlines continued to grow in the following few years, and despite filing for Chapter 11 protection in late 2008, it announced a profit for the first quarter of 2009.
- In July 2011, Sun Country Airlines was acquired by Cambria, a private company owned by the Davis family.
- In January, 2013, a new and improved Ufly Rewards program was launched, rewarding members for what they spend, not how far they fly. Introducing the concept of pooling, the program grants members the opportunity to pool points with up to 9 other Ufly members, to earn a free ticket, faster.
- Sun Country Airlines, an award-winning airline based in St. Paul, Minnesota, which flies to popular destinations in the U.S., the Caribbean and Mexico, has earned a reputation for offering world-class services at affordable prices.
In June 2015, Sun Country Airlines entered into a long-term agreement with Caesars Entertainment Corporation’s Total Rewards Air, the gaming industry’s largest domestic charter service. For the next three years, Sun Country Airlines will operate one Boeing 737-700 on behalf of Total Rewards Air and, together with ViaAir, will connect Total Rewards Air’s primary destination hubs (Atlantic City, Laughlin/Bullhead, Tunica, and Gulfport) with more than 100 origin cities across the US.
In September 2016, Sun Country Airlines launched its online store with exclusive branded merchandise from notable brands. Hometown Airline fans can now shop online for Sun Country-branded apparel, beachwear, model planes, gifts, and more.
- No deadly incidents involving the airline have been recorded so far.