Cheap Flights from OAK to CHI

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The Cheapest Round-trip Tickets from Oakland to Chicago

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2 June 20264 June 2026DirectAlaska AirlinesRT from 299

The Cheapest Flights for this Month from Oakland to Chicago

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21 May 202627 May 2026DirectSouthwest AirlinesRT from 509
22 May 202628 May 20261 StopAlaska AirlinesRT from 481
23 May 202628 May 20261 StopAlaska AirlinesRT from 444
24 May 202630 May 20261 StopSouthwest AirlinesRT from 365
25 May 202631 May 20261 StopAlaska AirlinesRT from 526
26 May 20261 June 20261 StopAlaska AirlinesRT from 480
28 May 20264 June 20261 StopAlaska AirlinesRT from 370
29 May 20261 June 2026DirectSouthwest AirlinesRT from 384
30 May 20261 June 20261 StopAlaska AirlinesRT from 473
2 June 20264 June 20261 StopAlaska AirlinesRT from 299
3 June 20265 June 20261 StopAlaska AirlinesRT from 357
5 June 20267 June 2026DirectSouthwest AirlinesRT from 481
7 June 20267 June 20261 StopSouthwest AirlinesRT from 500
21 June 202624 June 2026DirectSouthwest AirlinesRT from 372
24 June 202630 June 2026DirectSouthwest AirlinesRT from 405
25 June 202628 June 20261 StopAlaska AirlinesRT from 524
29 July 20263 August 20261 StopSouthwest AirlinesRT from 382
31 July 20263 August 20261 StopSouthwest AirlinesRT from 368
28 August 20263 September 2026DirectSouthwest AirlinesRT from 361

The Cheapest Flights from Oakland to Chicago for the Year Ahead

Departure atReturn atStopsAirlineFind tickets
24 May 202630 May 20261 StopSouthwest AirlinesRT from 365
2 June 20264 June 20261 StopAlaska AirlinesRT from 299
31 July 20263 August 20261 StopSouthwest AirlinesRT from 368
28 August 20263 September 2026DirectSouthwest AirlinesRT from 361
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