Cheap Flights from CHI to OAK

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The Cheapest Round-trip Tickets from Chicago to Oakland

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28 April 202630 April 2026DirectAlaska AirlinesRT from 244

The Cheapest Flights for this Month from Chicago to Oakland

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3 April 20266 April 2026DirectSouthwest AirlinesRT from 534
12 April 202619 April 2026DirectSouthwest AirlinesRT from 913
14 April 202621 April 20261 StopAlaska AirlinesRT from 311
15 April 202617 April 2026DirectSouthwest AirlinesRT from 433
16 April 202617 April 2026DirectSouthwest AirlinesRT from 459
17 April 202620 April 2026DirectSouthwest AirlinesRT from 334
19 April 202622 April 2026DirectSouthwest AirlinesRT from 422
20 April 202623 April 2026DirectSouthwest AirlinesRT from 296
26 April 202629 April 2026DirectSouthwest AirlinesRT from 452
27 April 202629 April 2026DirectSouthwest AirlinesRT from 248
28 April 202630 April 20261 StopAlaska AirlinesRT from 244
29 April 20266 May 20261 StopAlaska AirlinesRT from 271
1 May 20265 May 20261 StopAlaska AirlinesRT from 259
2 May 20269 May 20261 StopSouthwest AirlinesRT from 249
11 May 202618 May 20261 StopSouthwest AirlinesRT from 345
27 May 20262 June 2026DirectSouthwest AirlinesRT from 332
31 May 20264 June 2026DirectSouthwest AirlinesRT from 598
12 June 202614 June 2026DirectSouthwest AirlinesRT from 483
17 August 202621 August 20261 StopAlaska AirlinesRT from 357
4 September 20266 September 20261 StopAlaska AirlinesRT from 373

The Cheapest Flights from Chicago to Oakland for the Year Ahead

Departure atReturn atStopsAirlineFind tickets
28 April 202630 April 20261 StopAlaska AirlinesRT from 244
2 May 20269 May 20261 StopSouthwest AirlinesRT from 249
12 June 202614 June 2026DirectSouthwest AirlinesRT from 483
17 August 202621 August 20261 StopAlaska AirlinesRT from 357
4 September 20266 September 20261 StopAlaska AirlinesRT from 373
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