Cheap Flights from CHI to SJU

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The Cheapest Round-trip Tickets from Chicago to San Juan

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28 April 20265 May 2026DirectAmerican AirlinesRT from 185

The Cheapest Flights for this Month from Chicago to San Juan

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26 April 20263 May 20261 StopSpirit AirlinesRT from 197
28 April 20265 May 20261 StopAmerican AirlinesRT from 185
12 May 202619 May 20261 StopUnited AirlinesRT from 219
14 May 202622 May 2026DirectSpirit AirlinesRT from 186
1 June 20267 June 20262 StopsAmerican AirlinesRT from 272
16 June 202622 June 20261 StopAmerican AirlinesRT from 300
21 June 202624 June 20261 StopSpirit AirlinesRT from 351
23 June 20265 July 2026DirectFrontier AirlinesRT from 327
1 July 20267 July 2026DirectSpirit AirlinesRT from 308
26 July 20265 August 2026DirectSpirit AirlinesRT from 308
5 August 202610 August 20261 StopAmerican AirlinesRT from 299
6 August 202610 August 20261 StopFrontier AirlinesRT from 330
26 November 202629 November 2026DirectAmerican AirlinesRT from 712
19 December 20263 January 20272 StopsAmerican AirlinesRT from 989
21 December 202628 December 20261 StopAmerican AirlinesRT from 751
27 December 20261 January 20271 StopUnited AirlinesRT from 1 133
31 January 20275 February 2027DirectAmerican AirlinesRT from 492

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

Departure atReturn atStopsAirlineFind tickets
28 April 20265 May 20261 StopAmerican AirlinesRT from 185
14 May 202622 May 2026DirectSpirit AirlinesRT from 186
1 June 20267 June 20262 StopsAmerican AirlinesRT from 272
26 July 20265 August 2026DirectSpirit AirlinesRT from 308
5 August 202610 August 20261 StopAmerican AirlinesRT from 299
26 November 202629 November 2026DirectAmerican AirlinesRT from 712
21 December 202628 December 20261 StopAmerican AirlinesRT from 751
31 January 20275 February 2027DirectAmerican AirlinesRT from 492
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