Cheap Flights from SJC to MDW

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The Cheapest Round-trip Tickets from San Jose to

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23 February 202327 February 2023DirectRT from 342
3 September 202228 September 20221 StopRT from 292
4 November 20228 November 20222 StopsRT from 321

The Cheapest Flights for this Month from San Jose to

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7 August 202210 August 2022DirectRT from 692
9 August 202212 August 20221 StopRT from 656
12 August 202222 August 20222 StopsRT from 677
14 August 202221 August 20222 StopsRT from 1 225
18 August 202225 August 20221 StopRT from 739
23 August 202227 August 20222 StopsRT from 506
26 August 20221 September 20222 StopsRT from 501
27 August 202231 August 20221 StopRT from 459
31 August 20224 September 20222 StopsRT from 463
2 September 20225 September 20221 StopRT from 355
3 September 202228 September 20221 StopRT from 292
6 September 202216 September 20222 StopsRT from 452
9 September 202213 September 20222 StopsRT from 347
10 September 202213 September 20221 StopRT from 334
14 September 202228 September 20221 StopRT from 317
15 September 202222 September 20221 StopRT from 1 165
23 September 202226 September 20222 StopsRT from 619
11 October 202213 October 20222 StopsRT from 480
21 October 202227 October 20222 StopsRT from 517
28 October 20225 November 20222 StopsRT from 380
4 November 20228 November 20222 StopsRT from 321
16 November 202221 November 2022DirectRT from 462
8 December 202212 December 20221 StopRT from 348
11 December 202217 December 20221 StopRT from 468
19 December 202222 December 20221 StopRT from 690
23 February 202327 February 2023DirectRT from 342

The Cheapest Flights from San Jose to for the Year Ahead

Departure atReturn atStopsAirlineFind tickets
9 August 202212 August 20221 StopRT from 656
10 September 202213 September 20221 StopRT from 334
16 November 202221 November 2022DirectRT from 462
23 February 202327 February 2023DirectRT from 342
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