Cheap Flights from CHI to SJU

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The Cheapest Round-trip Tickets from Chicago to San Juan

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10 August 202613 August 2026DirectFrontier AirlinesRT from 269

The Cheapest Flights for this Month from Chicago to San Juan

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16 July 202619 July 2026DirectAmerican AirlinesRT from 372
17 July 202619 July 2026DirectFrontier AirlinesRT from 330
24 July 202627 July 2026DirectFrontier AirlinesRT from 400
31 July 20265 August 20262 StopsAllegiant AirRT from 346
5 August 202610 August 20262 StopsFrontier AirlinesRT from 361
6 August 202610 August 20261 StopAllegiant AirRT from 383
7 August 202616 August 20261 StopFrontier AirlinesRT from 369
9 August 202616 August 20262 StopsAllegiant AirRT from 355
10 August 202613 August 20261 StopFrontier AirlinesRT from 269
20 August 202623 August 2026DirectFrontier AirlinesRT from 271
9 September 202614 September 20261 StopSouthwest AirlinesRT from 276
12 September 202617 September 20261 StopFrontier AirlinesRT from 318
19 December 20263 January 20272 StopsFrontier AirlinesRT from 1 016

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

Departure atReturn atStopsAirlineFind tickets
17 July 202619 July 2026DirectFrontier AirlinesRT from 330
10 August 202613 August 20261 StopFrontier AirlinesRT from 269
9 September 202614 September 20261 StopSouthwest AirlinesRT from 276
19 December 20263 January 20272 StopsFrontier AirlinesRT from 1 016
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