Cheap Flights from MDW to OAK

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The Cheapest Round-trip Tickets from to Oakland

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27 April 202629 April 2026DirectSouthwest AirlinesRT from 248

The Cheapest Flights for this Month from to Oakland

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3 April 20266 April 2026DirectSouthwest AirlinesRT from 536
12 April 202619 April 2026DirectSouthwest AirlinesRT from 913
14 April 202621 April 2026DirectSouthwest AirlinesRT from 373
15 April 202617 April 2026DirectSouthwest AirlinesRT from 433
16 April 202617 April 2026DirectSouthwest AirlinesRT from 459
17 April 202620 April 2026DirectSouthwest AirlinesRT from 336
19 April 202622 April 2026DirectSouthwest AirlinesRT from 422
20 April 202623 April 2026DirectSouthwest AirlinesRT from 304
26 April 202629 April 2026DirectSouthwest AirlinesRT from 452
27 April 202629 April 2026DirectSouthwest AirlinesRT from 248
28 April 20262 May 2026DirectSouthwest AirlinesRT from 284
29 April 20266 May 2026DirectSouthwest AirlinesRT from 275
1 May 20265 May 2026DirectSouthwest AirlinesRT from 330
2 May 20269 May 2026DirectSouthwest AirlinesRT from 283
11 May 202618 May 2026DirectSouthwest AirlinesRT from 363
27 May 20262 June 2026DirectSouthwest AirlinesRT from 332
31 May 20264 June 2026DirectSouthwest AirlinesRT from 632
12 June 202614 June 2026DirectSouthwest AirlinesRT from 483
17 August 202621 August 2026DirectSouthwest AirlinesRT from 430
4 September 20266 September 2026DirectSouthwest AirlinesRT from 528

The Cheapest Flights from to Oakland for the Year Ahead

Departure atReturn atStopsAirlineFind tickets
27 April 202629 April 2026DirectSouthwest AirlinesRT from 248
2 May 20269 May 2026DirectSouthwest AirlinesRT from 283
12 June 202614 June 2026DirectSouthwest AirlinesRT from 483
17 August 202621 August 2026DirectSouthwest AirlinesRT from 430
4 September 20266 September 2026DirectSouthwest AirlinesRT from 528
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