Cheap Flights from CHI to SAN

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The Cheapest Round-trip Tickets from Chicago to San Diego

Departure atReturn atStopsAirlineFind tickets
1 May 20264 May 2026DirectSouthwest AirlinesRT from 136

The Cheapest Flights for this Month from Chicago to San Diego

Departure atReturn atStopsAirlineFind tickets
14 February 202615 February 2026DirectSouthwest AirlinesRT from 338
20 February 202623 February 20261 StopFrontier AirlinesRT from 184
21 February 202624 February 2026DirectUnited AirlinesRT from 216
26 February 20263 March 2026DirectUnited AirlinesRT from 226
6 March 20268 March 2026DirectAmerican AirlinesRT from 169
21 March 202628 March 20261 StopAmerican AirlinesRT from 302
22 March 202626 March 20261 StopAlaska AirlinesRT from 252
23 March 202625 March 2026DirectSouthwest AirlinesRT from 171
26 March 202628 March 20261 StopFrontier AirlinesRT from 256
27 March 20266 April 20262 StopsFrontier AirlinesRT from 310
31 March 20264 April 20261 StopAmerican AirlinesRT from 257
9 April 20269 May 2026DirectAlaska AirlinesRT from 142
22 April 202626 April 2026DirectAmerican AirlinesRT from 150
1 May 20264 May 2026DirectSouthwest AirlinesRT from 136

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

Departure atReturn atStopsAirlineFind tickets
20 February 202623 February 20261 StopFrontier AirlinesRT from 184
6 March 20268 March 2026DirectAmerican AirlinesRT from 169
9 April 20269 May 2026DirectAlaska AirlinesRT from 142
1 May 20264 May 2026DirectSouthwest AirlinesRT from 136
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