Cheap Flights from OAK to MDW

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The Cheapest Round-trip Tickets from Oakland to

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7 September 202614 September 2026DirectSouthwest AirlinesRT from 146

The Cheapest Flights for this Month from Oakland to

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20 July 202622 July 2026DirectSouthwest AirlinesRT from 642
31 July 20268 August 2026DirectSouthwest AirlinesRT from 556
1 August 20269 August 2026DirectSouthwest AirlinesRT from 668
2 August 20267 August 2026DirectSouthwest AirlinesRT from 545
3 August 20267 August 2026DirectSouthwest AirlinesRT from 542
6 August 20269 August 20261 StopSouthwest AirlinesRT from 383
27 August 202630 August 2026DirectSouthwest AirlinesRT from 460
7 September 202614 September 20261 StopSouthwest AirlinesRT from 146
7 October 202612 October 2026DirectSouthwest AirlinesRT from 436
5 February 202711 February 2027DirectSouthwest AirlinesRT from 360

The Cheapest Flights from Oakland to for the Year Ahead

Departure atReturn atStopsAirlineFind tickets
31 July 20268 August 2026DirectSouthwest AirlinesRT from 556
6 August 20269 August 20261 StopSouthwest AirlinesRT from 383
7 September 202614 September 20261 StopSouthwest AirlinesRT from 146
7 October 202612 October 2026DirectSouthwest AirlinesRT from 436
5 February 202711 February 2027DirectSouthwest AirlinesRT from 360
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