Cheap Flights from CHI to OAK

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The Cheapest Round-trip Tickets from Chicago to Oakland

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28 March 20262 April 2026DirectSouthwest AirlinesRT from 161

The Cheapest Flights for this Month from Chicago to Oakland

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15 February 202618 February 20261 StopAlaska AirlinesRT from 657
19 February 202622 February 20261 StopAlaska AirlinesRT from 693
21 February 202624 February 2026DirectSouthwest AirlinesRT from 611
25 February 202626 February 20261 StopAlaska AirlinesRT from 298
26 February 20263 March 20261 StopHawaiian AirlinesRT from 366
27 February 20262 March 20261 StopAlaska AirlinesRT from 463
10 March 202611 March 2026DirectSouthwest AirlinesRT from 252
13 March 202621 March 2026DirectSouthwest AirlinesRT from 215
14 March 202623 March 2026DirectSouthwest AirlinesRT from 207
15 March 202618 March 2026DirectSouthwest AirlinesRT from 549
16 March 202618 March 2026DirectSouthwest AirlinesRT from 311
19 March 202624 March 20261 StopSouthwest AirlinesRT from 218
20 March 202624 March 20261 StopSouthwest AirlinesRT from 218
21 March 202628 March 2026DirectSouthwest AirlinesRT from 419
28 March 20262 April 20262 StopsSouthwest AirlinesRT from 161
10 April 202612 April 2026DirectSouthwest AirlinesRT from 275
12 April 202615 April 2026DirectSouthwest AirlinesRT from 594
21 May 202624 May 20261 StopAlaska AirlinesRT from 322
30 May 20265 June 20261 StopJetHunterRT from 356
31 May 20265 June 2026DirectSouthwest AirlinesRT from 521
10 June 202614 June 20261 StopSouthwest AirlinesRT from 187
16 October 202623 October 20261 StopAlaska AirlinesRT from 338

The Cheapest Flights from Chicago to Oakland for the Year Ahead

Departure atReturn atStopsAirlineFind tickets
25 February 202626 February 20261 StopAlaska AirlinesRT from 298
28 March 20262 April 20262 StopsSouthwest AirlinesRT from 161
10 April 202612 April 2026DirectSouthwest AirlinesRT from 275
21 May 202624 May 20261 StopAlaska AirlinesRT from 322
10 June 202614 June 20261 StopSouthwest AirlinesRT from 187
16 October 202623 October 20261 StopAlaska AirlinesRT from 338
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