Cheap Flights from MDW to SJC

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The Cheapest Round-trip Tickets from to San Jose

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7 May 20269 May 2026DirectSouthwest AirlinesRT from 333

The Cheapest Flights for this Month from to San Jose

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22 April 202626 April 2026DirectSouthwest AirlinesRT from 1 024
23 April 202630 April 2026DirectSouthwest AirlinesRT from 631
24 April 202627 April 2026DirectSouthwest AirlinesRT from 638
27 April 202630 April 2026DirectSouthwest AirlinesRT from 630
2 May 20269 May 2026DirectSouthwest AirlinesRT from 439
7 May 20269 May 2026DirectSouthwest AirlinesRT from 333
23 May 202625 May 2026DirectSouthwest AirlinesRT from 429
29 May 20261 June 2026DirectSouthwest AirlinesRT from 369
5 June 20267 June 2026DirectSouthwest AirlinesRT from 424
19 June 202622 June 2026DirectSouthwest AirlinesRT from 421
23 June 202627 June 2026DirectSouthwest AirlinesRT from 513
24 June 202628 June 2026DirectSouthwest AirlinesRT from 489
30 June 202614 July 2026DirectSouthwest AirlinesRT from 475
21 July 20264 August 2026DirectSouthwest AirlinesRT from 394
12 September 202619 September 2026DirectSouthwest AirlinesRT from 414

The Cheapest Flights from to San Jose for the Year Ahead

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27 April 202630 April 2026DirectSouthwest AirlinesRT from 630
7 May 20269 May 2026DirectSouthwest AirlinesRT from 333
19 June 202622 June 2026DirectSouthwest AirlinesRT from 421
21 July 20264 August 2026DirectSouthwest AirlinesRT from 394
12 September 202619 September 2026DirectSouthwest AirlinesRT from 414
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