Cheap Flights from MDW to SJU

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The Cheapest Round-trip Tickets from to San Juan

Departure atReturn atStopsAirlineFind tickets
24 April 20261 May 2026DirectSouthwest AirlinesRT from 184

The Cheapest Flights for this Month from to San Juan

Departure atReturn atStopsAirlineFind tickets
16 February 20269 March 20261 StopFrontier AirlinesRT from 275
23 February 20269 March 20261 StopFrontier AirlinesRT from 219
24 February 20266 March 20261 StopFrontier AirlinesRT from 242
25 February 20267 March 20262 StopsFrontier AirlinesRT from 301
26 February 202628 February 20261 StopFrontier AirlinesRT from 246
27 February 202613 March 20261 StopFrontier AirlinesRT from 362
1 March 202615 March 20261 StopFrontier AirlinesRT from 470
2 March 20266 March 20261 StopFrontier AirlinesRT from 221
3 March 202617 March 20261 StopFrontier AirlinesRT from 229
6 March 20269 March 20261 StopFrontier AirlinesRT from 276
9 March 202616 March 20261 StopFrontier AirlinesRT from 230
12 March 202616 March 20262 StopsFrontier AirlinesRT from 434
17 March 202620 March 20261 StopFrontier AirlinesRT from 668
19 March 202624 March 20261 StopFrontier AirlinesRT from 239
20 March 202628 March 20263 StopsFrontier AirlinesRT from 484
26 March 202631 March 20262 StopsFrontier AirlinesRT from 363
27 March 20266 April 20261 StopFrontier AirlinesRT from 567
2 April 20265 April 20261 StopFrontier AirlinesRT from 519
6 April 202616 April 20261 StopFrontier AirlinesRT from 239
9 April 202612 April 20261 StopFrontier AirlinesRT from 726
16 April 202622 April 20262 StopsFrontier AirlinesRT from 333
22 April 202629 April 20261 StopSouthwest AirlinesRT from 199
24 April 20261 May 20262 StopsSouthwest AirlinesRT from 184
27 April 202628 April 20261 StopSouthwest AirlinesRT from 292
30 April 20263 May 20261 StopFrontier AirlinesRT from 382
15 May 202619 May 20261 StopSouthwest AirlinesRT from 327
1 June 20267 June 20261 StopSouthwest AirlinesRT from 382
4 June 20267 June 20261 StopSouthwest AirlinesRT from 403
13 July 202623 July 20261 StopSouthwest AirlinesRT from 472
20 July 202626 July 20261 StopSouthwest AirlinesRT from 510
28 August 202622 September 20261 StopSouthwest AirlinesRT from 489
20 September 202630 September 20261 StopSouthwest AirlinesRT from 462
19 December 20263 January 20272 StopsPorter AirlinesRT from 1 166

The Cheapest Flights from to San Juan for the Year Ahead

Departure atReturn atStopsAirlineFind tickets
23 February 20269 March 20261 StopFrontier AirlinesRT from 219
2 March 20266 March 20261 StopFrontier AirlinesRT from 221
24 April 20261 May 20262 StopsSouthwest AirlinesRT from 184
15 May 202619 May 20261 StopSouthwest AirlinesRT from 327
1 June 20267 June 20261 StopSouthwest AirlinesRT from 382
13 July 202623 July 20261 StopSouthwest AirlinesRT from 472
28 August 202622 September 20261 StopSouthwest AirlinesRT from 489
20 September 202630 September 20261 StopSouthwest AirlinesRT from 462
19 December 20263 January 20272 StopsPorter AirlinesRT from 1 166
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