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The airline was established by Doug Voss and Ivan Simpson and started operations on April 5, 1977. It began scheduled services on October 12, 1981, with flights between Spencer, Iowa, and Des Moines, Iowa. In February 1988, Great Lakes acquired Alliance Airlines, adding six cities around Lake Michigan to the route network. In the following years it continued to expand and in February 1992 signed a codesharing agreement with United Airlines. On January 19, 1994, the airline went public trading on the NASDAQ stock exchange. In October 1995, Great Lakes began operating under the Midway Connection banner at Raleigh/Durham through a marketing agreement with Midway Airlines, but this ceased in 1997. Prior to the relocation of the headquarters to Cheyenne, Great Lakes was headquartered in Summit Township, Clay County, Iowa, by Spencer Municipal Airport and near the city of Spencer.
 
Its status with United Express was downgraded to a codeshare agreement in 2001 and on May 1, 2001, it became an independent carrier. Great Lakes has code sharing agreements with United Airlines and Frontier Airlines.
 
The airline added service to a new hub serving Las Vegas, Nevada, on April 7, 2010. Also the airline created a hub at Minneapolis, Minnesota, on March 17, 2012.

Transitioned to FAR Part 135 regulations on in April 2014 in response to the change of hiring minimums of 1,500 hours total time to act as a crew member on a scheduled Part 121 flight.

1977
Great Lakes Aviation traces its success back to April 15th with the creation of Spirit Lake Airways. Found by Doug Voss and Ivan Simpson in Spirit Lake, Iowa, the company offered flight instruction, charter service, and aircraft maintenance.
1979
Great Lakes Aviation officially incorporated on October 25th; the Company name change reflected its expansion in the Iowa Great Lakes Region of Northwest Iowa.
1981
First scheduled passenger flight began on October 12th between between Spencer and Des Moines, Iowa.
1983
On June 15th, the company acquired its first of eight Beechcraft 99 Turboprop airliners.
1985
In August, the company acquired its first Chicago O' Hare landing FAA slot lottery. This event allowed the beginning of scheduled service to Chicago O' Hare. In October , Great Lakes Aviation was selected by the U.S. Department of Transportation to provide service to its first subsidized Essential Air Service Routes.
1987
Great Lakes Aviation took delivery of their first Beechcraft 1900 Turboprop airliner with 19-seat capacity.
1988
April 1st Great Lakes acquired Alliance Airline's route structures and it's Chicago O'Hare landing slots, greatly enhancing the companies presence at Chicago O'Hare.
1991
In June, Great Lakes began providing scheduled air service to Denver's Stapleton Airport from cities in, Iowa, Nebraska and North Dakota.
1992
On April 25th Great Lakes Aviation inaugurated service as a United Express carrier through a comprehensive marketing agreement with United Airlines.
1994
On January 20th, the Company completed an initial public offering of its stock trading on the NASDAQ exchange under GLUX. The proceeds allowed the acquisition of larger aircraft. In May, Great Lakes Aviation purchased it's first of twelve Embraer Brasilia aircraft, which provide 30-seat capacity and in-flight service. The company also took delivery of its first Beechcraft 1900D airliner, which features a stand-up cabin enhancing passenger comfort.
1998
Great Lakes Aviation was selected by United Airlines to provide regional air service at 20 locations in Wyoming, Colorado, New Mexico, Kansas and Nebraska to feed the Denver Hub.
1999
Great Lakes Aviation signed a lease with the Cheyenne Airport in May that facilitated a move from Spencer, Iowa to Cheyenne, Wyoming. The state of Wyoming provided funding to build a new maintenance facility and corporate headquarters for Great Lakes Aviation. Construction began in August.
2000
The move into the final phase of the new Corporate Headquarters was complete and creating approximately 150 new positions in Wyoming.
2001
On May 1st, Great Lakes Aviation announced a re-branding from the United Express to it's own independent identity "Great Lakes Airlines." A new code-share agreement with United Airlines was negotiated, allowing the company to arrange similar code-sharing relationships with other airlines. On July 9th, a code-share agreement began with Frontier Airlines bringing their affordable fares to communities served by Great Lakes Airlines.
2002
In August, Great Lakes welcomed new CEO, Chuck Howell. Mr. Howell came to Great Lakes from Nashville, Tennessee, where he served the previous six years as President/CEO of Corporate Airlines - a regional airline that has code-share agreements with Midway, Trans World and American Airlines.
2006
Great Lakes Airlines began offering their own inflight magazine, 'Peaks & Plains', to spotlight the small communities they serve.
2008
Great Lakes Airlines entered into its first Interline Electronic Ticketing agreement with US Airways allowing for a Great Lakes flight to be purchased in combination with a US Airways flight and passengers receive just one ticket.
2011
Great Lakes celebrates its 30th year of airline service. They sign Interline Electronic Ticketing agreements with American Airlines and Delta Airlines. Great Lakes began expanding to 7 new communities with service into Minneapolis/St. Paul International Airport (MSP).
2012
The expansion into MSP continued well into 2012, returning Great Lakes to the hub city where its headquarters were located for a short period of time.

In 2013, a new government ruling requiring first officers to have a minimum of 1500 flight hours and restrictions on crew rest and duty times created a severe hardship for Great Lakes as well as many other commuter airlines. The airline was then forced to pull ten seats out of most of its 19-seat Beech 1900D aircraft. Many flights had to be cancelled as well as all service to several cities including Mason City Municipal Airport.[9] On April 1, 2015, service to Sheridan, Wyoming was dropped leaving the remote city with no air service. Sheridan had been served since the early days of aviation by many airlines, some with jets including Boeing 737s by Western Airlines. Most routes Great Lakes has served are subsidized through Essential Air Service. Through its history the airline is known to have served at least 162 cities and 164 airports (three at Chicago) but was down to only seven cities as of March 22, 2018.

Great Lakes had a rather unusual theme where many of their Beech 1900D aircraft had their tails painted advertising cities that they flew to as well as National Parks in their territory. Some of the tails advertised the cities of Laramie, Wyoming; Alamosa and Telluride, Colorado; Scottsbluff, Nebraska; Ponca City, Oklahoma; Garden City, Kansas, Dodge City, Kansas and Liberal, Kansas; Sierra Vista, Arizona; Pierre, South Dakota; Miles City, Montana, as well as the White Mountains of Arizona, the Teton Range and Devils Tower in Wyoming.

On June 2, 2016, Great Lakes Airlines, Silver Airways and Frontier Airlines announced a partnership for recruiting pilots.

On March 26, 2018, Great Lakes Airlines announced that operations would be suspended effective at midnight. Despite ceasing operations, the company didn't file for bankruptcy and certain segments of the company continued to operate. Flights to Pierre, South Dakota and Watertown, South Dakota continued to operate through Great Lakes Jet Express.

On March 26, 2018, Great Lakes Airlines announced that operations would be suspended effective at midnight. However, certain segments of the company continue to operate, including Great Lakes Jet Express flights to Pierre and Watertown in South Dakota. Ground employees handling ADI's flights became employees of ADI, although Great Lakes continued handling ADI's ticketing for a time.

On May 29, 2018, ADI was purchased by California Pacific Airlines. For a few months it did business as California Pacific on the Pierre/Watertown route, as well as California Pacific's intended markets out of McClellan–Palomar Airport. However, in December 2018 CPA suspended its West Coast operations, and in January 2019 its EAS operations were abruptly shut down as well, leaving Pierre (the capital of South Dakota) and Watertown without any scheduled commercial air service.


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