Cheap Flights from MDW to SAN

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The Cheapest Round-trip Tickets from to San Diego

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1 May 20264 May 2026DirectSouthwest AirlinesRT from 174

The Cheapest Flights for this Month from to San Diego

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14 February 202615 February 2026DirectSouthwest AirlinesRT from 338
20 February 202623 February 2026DirectSouthwest AirlinesRT from 240
21 February 202624 February 2026DirectSouthwest AirlinesRT from 240
26 February 20263 March 2026DirectSouthwest AirlinesRT from 354
2 March 20266 March 20261 StopFrontier AirlinesRT from 195
6 March 20268 March 2026DirectSouthwest AirlinesRT from 282
19 March 202623 March 2026DirectSouthwest AirlinesRT from 251
21 March 202628 March 20261 StopSouthwest AirlinesRT from 534
22 March 202626 March 20261 StopSouthwest AirlinesRT from 376
23 March 202625 March 20261 StopSouthwest AirlinesRT from 210
26 March 202628 March 20261 StopFrontier AirlinesRT from 427
27 March 20266 April 20262 StopsSouthwest AirlinesRT from 349
31 March 20264 April 20261 StopSouthwest AirlinesRT from 262
9 April 20269 May 2026DirectSouthwest AirlinesRT from 183
22 April 202626 April 20261 StopSouthwest AirlinesRT from 198
1 May 20264 May 2026DirectSouthwest AirlinesRT from 174

The Cheapest Flights from to San Diego for the Year Ahead

Departure atReturn atStopsAirlineFind tickets
20 February 202623 February 2026DirectSouthwest AirlinesRT from 240
2 March 20266 March 20261 StopFrontier AirlinesRT from 195
9 April 20269 May 2026DirectSouthwest AirlinesRT from 183
1 May 20264 May 2026DirectSouthwest AirlinesRT from 174
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