Cheap Flights from MDW to SJC

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The Cheapest Round-trip Tickets from to San Jose

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5 June 20269 June 2026DirectSouthwest AirlinesRT from 331

The Cheapest Flights for this Month from to San Jose

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2 May 20269 May 2026DirectSouthwest AirlinesRT from 924
10 May 202612 May 20261 StopSouthwest AirlinesRT from 597
14 May 202617 May 2026DirectSouthwest AirlinesRT from 587
19 May 202622 May 2026DirectSouthwest AirlinesRT from 533
22 May 202625 May 2026DirectSouthwest AirlinesRT from 459
23 May 202625 May 2026DirectSouthwest AirlinesRT from 439
30 May 20263 June 2026DirectSouthwest AirlinesRT from 413
31 May 20263 June 2026DirectSouthwest AirlinesRT from 493
1 June 20264 June 2026DirectSouthwest AirlinesRT from 500
5 June 20269 June 2026DirectSouthwest AirlinesRT from 331
16 June 202624 June 2026DirectSouthwest AirlinesRT from 420
12 July 202618 July 20261 StopSouthwest AirlinesRT from 370
18 September 202627 September 2026DirectSouthwest AirlinesRT from 440

The Cheapest Flights from to San Jose for the Year Ahead

Departure atReturn atStopsAirlineFind tickets
30 May 20263 June 2026DirectSouthwest AirlinesRT from 413
5 June 20269 June 2026DirectSouthwest AirlinesRT from 331
12 July 202618 July 20261 StopSouthwest AirlinesRT from 370
18 September 202627 September 2026DirectSouthwest AirlinesRT from 440
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