Cheap Flights from MDW to OAK

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The Cheapest Round-trip Tickets from to Oakland

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18 September 202621 September 2026DirectSouthwest AirlinesRT from 278

The Cheapest Flights for this Month from to Oakland

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5 September 20268 September 2026DirectSouthwest AirlinesRT from 500
10 September 202613 September 2026DirectSouthwest AirlinesRT from 507
11 September 202615 September 2026DirectSouthwest AirlinesRT from 354
18 September 202621 September 2026DirectSouthwest AirlinesRT from 278
25 September 202629 September 2026DirectSouthwest AirlinesRT from 308
10 October 202612 October 2026DirectSouthwest AirlinesRT from 364
5 November 20268 November 2026DirectSouthwest AirlinesRT from 308
14 April 202717 April 2027DirectSouthwest AirlinesRT from 368
15 April 202717 April 2027DirectSouthwest AirlinesRT from 368
16 April 202719 April 2027DirectSouthwest AirlinesRT from 367
17 April 202717 April 2027DirectSouthwest AirlinesRT from 419

The Cheapest Flights from to Oakland for the Year Ahead

Departure atReturn atStopsAirlineFind tickets
18 September 202621 September 2026DirectSouthwest AirlinesRT from 278
10 October 202612 October 2026DirectSouthwest AirlinesRT from 364
5 November 20268 November 2026DirectSouthwest AirlinesRT from 308
16 April 202719 April 2027DirectSouthwest AirlinesRT from 367
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