Cheap Flights from MDW to OAK

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The Cheapest Round-trip Tickets from to Oakland

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21 July 20264 August 2026DirectSouthwest AirlinesRT from 356

The Cheapest Flights for this Month from to Oakland

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21 April 202622 April 2026DirectSouthwest AirlinesRT from 505
22 April 202625 April 2026DirectSouthwest AirlinesRT from 495
23 April 202630 April 2026DirectSouthwest AirlinesRT from 526
25 April 202625 April 2026DirectSouthwest AirlinesRT from 752
27 April 202630 April 2026DirectSouthwest AirlinesRT from 525
2 May 20269 May 2026DirectSouthwest AirlinesRT from 440
23 May 202625 May 2026DirectSouthwest AirlinesRT from 356
30 May 202618 June 2026DirectSouthwest AirlinesRT from 510
1 June 202626 June 2026DirectSouthwest AirlinesRT from 463
5 June 20267 June 2026DirectSouthwest AirlinesRT from 396
14 June 202620 June 2026DirectSouthwest AirlinesRT from 561
19 June 202622 June 2026DirectSouthwest AirlinesRT from 406
30 June 202614 July 2026DirectSouthwest AirlinesRT from 475
21 July 20264 August 2026DirectSouthwest AirlinesRT from 356
12 September 202619 September 2026DirectSouthwest AirlinesRT from 386

The Cheapest Flights from to Oakland for the Year Ahead

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22 April 202625 April 2026DirectSouthwest AirlinesRT from 495
23 May 202625 May 2026DirectSouthwest AirlinesRT from 356
5 June 20267 June 2026DirectSouthwest AirlinesRT from 396
21 July 20264 August 2026DirectSouthwest AirlinesRT from 356
12 September 202619 September 2026DirectSouthwest AirlinesRT from 386
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