Cheap Flights from CHI to SJC

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The Cheapest Round-trip Tickets from Chicago to San Jose

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1 May 20265 May 2026DirectAlaska AirlinesRT from 236

The Cheapest Flights for this Month from Chicago to San Jose

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3 April 20266 April 20261 StopHawaiian AirlinesRT from 475
12 April 202619 April 20261 StopUnited AirlinesRT from 713
14 April 202621 April 2026DirectSouthwest AirlinesRT from 423
15 April 202616 April 20261 StopAlaska AirlinesRT from 270
16 April 202617 April 20261 StopAlaska AirlinesRT from 270
17 April 202620 April 2026DirectSouthwest AirlinesRT from 385
19 April 202620 April 20261 StopSpirit AirlinesRT from 363
20 April 202622 April 20261 StopAlaska AirlinesRT from 290
26 April 202629 April 2026DirectUnited AirlinesRT from 374
27 April 202629 April 2026DirectSouthwest AirlinesRT from 248
28 April 202630 April 20261 StopAlaska AirlinesRT from 237
29 April 20266 May 20261 StopFrontier AirlinesRT from 241
1 May 20265 May 20261 StopAlaska AirlinesRT from 236
2 May 20269 May 20261 StopSouthwest AirlinesRT from 249
11 May 202618 May 20261 StopSpirit AirlinesRT from 293
27 May 20262 June 20262 StopsFrontier AirlinesRT from 334
31 May 20264 June 2026DirectSouthwest AirlinesRT from 493
12 June 202614 June 2026DirectSouthwest AirlinesRT from 494
17 August 202621 August 20261 StopAlaska AirlinesRT from 302
4 September 20266 September 20261 StopAlaska AirlinesRT from 342

The Cheapest Flights from Chicago to San Jose for the Year Ahead

Departure atReturn atStopsAirlineFind tickets
28 April 202630 April 20261 StopAlaska AirlinesRT from 237
1 May 20265 May 20261 StopAlaska AirlinesRT from 236
12 June 202614 June 2026DirectSouthwest AirlinesRT from 494
17 August 202621 August 20261 StopAlaska AirlinesRT from 302
4 September 20266 September 20261 StopAlaska AirlinesRT from 342
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