Cheap Flights from MDW to SJU

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The Cheapest Round-trip Tickets from to San Juan

Departure atReturn atStopsAirlineFind tickets
9 September 202614 September 2026DirectSouthwest AirlinesRT from 276

The Cheapest Flights for this Month from to San Juan

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16 July 202619 July 20261 StopSouthwest AirlinesRT from 514
17 July 202619 July 20261 StopFrontier AirlinesRT from 523
24 July 202627 July 20261 StopSouthwest AirlinesRT from 487
31 July 20265 August 20261 StopFrontier AirlinesRT from 469
5 August 202610 August 20262 StopsFrontier AirlinesRT from 394
6 August 202610 August 20262 StopsFrontier AirlinesRT from 487
7 August 202616 August 20261 StopFrontier AirlinesRT from 456
9 August 202616 August 20261 StopSouthwest AirlinesRT from 434
10 August 202613 August 20261 StopSouthwest AirlinesRT from 300
20 August 202623 August 20261 StopFrontier AirlinesRT from 357
9 September 202614 September 20261 StopSouthwest AirlinesRT from 276
12 September 202617 September 20261 StopSouthwest AirlinesRT from 354
19 December 20263 January 20271 StopFrontier AirlinesRT from 1 302

The Cheapest Flights from to San Juan for the Year Ahead

Departure atReturn atStopsAirlineFind tickets
31 July 20265 August 20261 StopFrontier AirlinesRT from 469
10 August 202613 August 20261 StopSouthwest AirlinesRT from 300
9 September 202614 September 20261 StopSouthwest AirlinesRT from 276
19 December 20263 January 20271 StopFrontier AirlinesRT from 1 302
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