Cheap Flights from MDW to SJU

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The Cheapest Round-trip Tickets from to San Juan

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28 April 20265 May 2026DirectSouthwest AirlinesRT from 232

The Cheapest Flights for this Month from to San Juan

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26 April 20263 May 20261 StopFrontier AirlinesRT from 232
28 April 20265 May 20261 StopSouthwest AirlinesRT from 232
12 May 202619 May 20261 StopSouthwest AirlinesRT from 253
14 May 202622 May 20262 StopsSouthwest AirlinesRT from 302
1 June 20267 June 20261 StopFrontier AirlinesRT from 490
16 June 202622 June 20262 StopsFrontier AirlinesRT from 309
21 June 202624 June 20261 StopFrontier AirlinesRT from 499
23 June 20265 July 20262 StopsFrontier AirlinesRT from 447
1 July 20267 July 20261 StopSouthwest AirlinesRT from 420
26 July 20265 August 20261 StopFrontier AirlinesRT from 359
5 August 202610 August 20261 StopSouthwest AirlinesRT from 339
6 August 202610 August 20262 StopsFrontier AirlinesRT from 404
19 December 20263 January 20273 StopsWestJetRT from 1 438

The Cheapest Flights from to San Juan for the Year Ahead

Departure atReturn atStopsAirlineFind tickets
28 April 20265 May 20261 StopSouthwest AirlinesRT from 232
12 May 202619 May 20261 StopSouthwest AirlinesRT from 253
16 June 202622 June 20262 StopsFrontier AirlinesRT from 309
26 July 20265 August 20261 StopFrontier AirlinesRT from 359
5 August 202610 August 20261 StopSouthwest AirlinesRT from 339
19 December 20263 January 20273 StopsWestJetRT from 1 438
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