The announcement of the Dole Air Race for a flight from California to Hawaii provided the incentive to purchase 680 acres (280 ha) in April 1927 for the airport.

It was transformed into an airlift base for military flights to the Pacific islands, ordering all scheduled services to move to San Francisco International Airport.

The 1990s saw a rise of low-cost carriers serving Oakland, Morris Air (later merged into Southwest Airlines), and MarkAir to name a few, provided several domestic destinations from OAK.

During the 1990s, tour operator SunTrips contracted Aerocancun and Leisure Air to provide scheduled charter flights from OAK to sun destinations during the early 1990s.

[8] United Airlines vacated its 300,000 sq ft (30,000 m2) Oakland Maintenance Center in May 2003 and transferred work to its base across the bay at San Francisco International Airport (SFO).

Oakland International Airport began a $300 million expansion and renovation project in 2004, including adding five gates in Terminal 2.

[8] In 2008, Oakland saw a series of cutbacks due to high fuel costs and airline bankruptcies, more than other Bay Area airports.

In 2009, Allegiant Air moved operations from San Francisco International Airport, before designating OAK as a focus city.

In the same year, Volaris began service to OAK as their first destination in the San Francisco Bay Area and held a commercial agreement with Southwest Airlines, until its merger with AirTran Airways in 2011.

AirAsia executives had new optimism that service between the U.S. and the airline's main base in Kuala Lumpur, could possibly happen earlier than originally expected, but has yet to come to fruition as of 2020.

[12][13] In 2011, Spirit Airlines returned to OAK after several years of absence, eventually flying a combined total of seven year-round and seasonal routes by the summer of 2017.

Oakland International Airport also celebrated its 85th anniversary in 2011, commemorating the first transpacific crossing by air from OAK to Hawaii, which took place on June 29, 1927, in The Bird of Paradise, flown by Hegenberger and Maitland.

In 2012 United Airlines pulled out of OAK, consolidating operations at San Francisco International Airport, its Bay Area hub.

Arkefly (which later re-branded as TUI Airlines Netherlands) chose OAK as a San Francisco Bay Area gateway, flying twice weekly to Amsterdam, via a stop at Los Angeles International Airport.

In 2013, FedEx Express opened a $30 million upgrade of its hub facility at OAK, including additions to accommodate the airline's new Boeing 777 Freighter fleet.

The flights were the first-ever nonstop services offered from the two Scandinavian capitals to the San Francisco Bay Area, providing several connections throughout Europe.

[15] In May 2015, Oakland International Airport's Moving Modern program construction commenced a $100 million renovation of the Terminal 1 complex.

The project included seismic architectural retrofits in central buildings, replacement and upgrading of infrastructure and improvement of the passenger environment.

[19] Between mid-2018 and early 2020, OAK had both lost and was losing domestic and international nonstop routes; the indefinite grounding of the Boeing 737 MAX by both Southwest and American, the "restructuring" of schedules by airlines, and a lack of demand all contribute to this.

Southwest Airlines ended systemwide service with Newark Liberty International Airport in November 2019, followed by discontinuing three more routes with OAK effective January 2020.

[22][24] The confusion has been especially severe for Chinese-speaking travelers, because the two cities' names are written identically in simplified Chinese ("奥克兰") and must be distinguished by context.

[27] On November 12, 2024, U.S. Magistrate Judge Thomas S. Hixson granted SFO's motion for a preliminary injunction and ordered OAK to stop using the words "San Francisco Bay" in its name while the case remained pending (that is, through trial on the merits of the parties' claims).

[39] More than 95% of the time, winds in the area blow from the west or north, and aircraft arrive at Oakland from the southeast and depart to the northwest.

On occasions when winds blow from the east or south, aircraft operate in the other direction, arriving from the northwest and departing to the southeast.

[41] KaiserAir also provides FBO services at Oakland's North Field, performing maintenance on Gulfstream, Hawker, Cessna and other business jet aircraft.

The airport is accessible by private automobile from Interstate 880 (Nimitz Freeway) which is 2 miles (3 km) away via Hegenberger Road or 98th Avenue heading west.

[43][44] Ward Allen advocated for its approval before several transportation authorities endorsed the project, which created between 2,500 and 5,200 direct and indirect jobs.

[45][46][47] Some critics of the project argued that the money would be better spent on supporting existing local transit agencies, which had financial issues at the time.