Cheap Flights from OAK to MDW

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The Cheapest Round-trip Tickets from Oakland to

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2 June 20264 June 2026DirectSouthwest AirlinesRT from 338

The Cheapest Flights for this Month from Oakland to

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21 May 202627 May 2026DirectSouthwest AirlinesRT from 509
22 May 202628 May 2026DirectSouthwest AirlinesRT from 505
23 May 202628 May 2026DirectSouthwest AirlinesRT from 468
24 May 202630 May 20261 StopSouthwest AirlinesRT from 365
25 May 202631 May 2026DirectSouthwest AirlinesRT from 591
26 May 20261 June 2026DirectSouthwest AirlinesRT from 545
28 May 20264 June 2026DirectSouthwest AirlinesRT from 441
29 May 20261 June 2026DirectSouthwest AirlinesRT from 399
30 May 20261 June 2026DirectSouthwest AirlinesRT from 545
2 June 20264 June 2026DirectSouthwest AirlinesRT from 338
3 June 20265 June 2026DirectSouthwest AirlinesRT from 371
5 June 20267 June 2026DirectSouthwest AirlinesRT from 494
7 June 20267 June 20261 StopSouthwest AirlinesRT from 500
21 June 202624 June 2026DirectSouthwest AirlinesRT from 418
24 June 202629 June 2026DirectSouthwest AirlinesRT from 461
25 June 202628 June 2026DirectSouthwest AirlinesRT from 624
29 July 20263 August 20261 StopSouthwest AirlinesRT from 382
31 July 20263 August 20261 StopSouthwest AirlinesRT from 428
28 August 20263 September 2026DirectSouthwest AirlinesRT from 361

The Cheapest Flights from Oakland to for the Year Ahead

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24 May 202630 May 20261 StopSouthwest AirlinesRT from 365
2 June 20264 June 2026DirectSouthwest AirlinesRT from 338
29 July 20263 August 20261 StopSouthwest AirlinesRT from 382
28 August 20263 September 2026DirectSouthwest AirlinesRT from 361
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