Cheap Flights from MDW to SJC

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The Cheapest Round-trip Tickets from to San Jose

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10 June 202614 June 2026DirectSouthwest AirlinesRT from 203

The Cheapest Flights for this Month from to San Jose

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15 February 202618 February 2026DirectSouthwest AirlinesRT from 1 044
19 February 202622 February 2026DirectSouthwest AirlinesRT from 1 030
21 February 202624 February 2026DirectSouthwest AirlinesRT from 684
26 February 202628 February 2026DirectSouthwest AirlinesRT from 579
27 February 20262 March 2026DirectSouthwest AirlinesRT from 629
10 March 202611 March 2026DirectSouthwest AirlinesRT from 297
13 March 202621 March 2026DirectSouthwest AirlinesRT from 233
15 March 202618 March 2026DirectSouthwest AirlinesRT from 483
16 March 202618 March 2026DirectSouthwest AirlinesRT from 337
19 March 202624 March 2026DirectSouthwest AirlinesRT from 316
20 March 202624 March 2026DirectSouthwest AirlinesRT from 336
21 March 202628 March 20261 StopSouthwest AirlinesRT from 521
28 March 20262 April 20261 StopSouthwest AirlinesRT from 463
10 April 202612 April 2026DirectSouthwest AirlinesRT from 334
12 April 202615 April 2026DirectSouthwest AirlinesRT from 619
24 April 202628 April 2026DirectSouthwest AirlinesRT from 332
25 April 202627 April 2026DirectSouthwest AirlinesRT from 312
21 May 202624 May 2026DirectSouthwest AirlinesRT from 459
30 May 20265 June 2026DirectSouthwest AirlinesRT from 391
31 May 20265 June 2026DirectSouthwest AirlinesRT from 391
10 June 202614 June 2026DirectSouthwest AirlinesRT from 203

The Cheapest Flights from to San Jose for the Year Ahead

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26 February 202628 February 2026DirectSouthwest AirlinesRT from 579
13 March 202621 March 2026DirectSouthwest AirlinesRT from 233
25 April 202627 April 2026DirectSouthwest AirlinesRT from 312
30 May 20265 June 2026DirectSouthwest AirlinesRT from 391
10 June 202614 June 2026DirectSouthwest AirlinesRT from 203
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