Cheap Flights from CHI to SJU

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The Cheapest Round-trip Tickets from Chicago to San Juan

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24 April 20261 May 2026DirectAmerican AirlinesRT from 149

The Cheapest Flights for this Month from Chicago to San Juan

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16 February 20269 March 20261 StopSpirit AirlinesRT from 262
23 February 20269 March 20261 StopSpirit AirlinesRT from 177
24 February 20266 March 2026DirectSpirit AirlinesRT from 172
25 February 202610 March 20261 StopFrontier AirlinesRT from 190
26 February 202628 February 20261 StopSpirit AirlinesRT from 182
27 February 202613 March 20261 StopFrontier AirlinesRT from 215
1 March 202615 March 20261 StopFrontier AirlinesRT from 278
2 March 20266 March 2026DirectSpirit AirlinesRT from 167
3 March 202613 March 2026DirectSpirit AirlinesRT from 173
4 March 202613 March 20261 StopFrontier AirlinesRT from 180
6 March 20269 March 20261 StopFrontier AirlinesRT from 276
9 March 202613 March 20261 StopFrontier AirlinesRT from 199
12 March 202616 March 20261 StopFrontier AirlinesRT from 256
17 March 202620 March 20261 StopSpirit AirlinesRT from 272
19 March 202624 March 20261 StopFrontier AirlinesRT from 227
26 March 20262 April 20262 StopsFrontier AirlinesRT from 370
27 March 20261 April 20261 StopFrontier AirlinesRT from 322
28 March 202631 March 20261 StopSpirit AirlinesRT from 307
2 April 20265 April 20261 StopFrontier AirlinesRT from 473
6 April 202616 April 20261 StopSpirit AirlinesRT from 170
9 April 202612 April 20261 StopFrontier AirlinesRT from 292
16 April 202622 April 20261 StopFrontier AirlinesRT from 205
22 April 202629 April 20261 StopAmerican AirlinesRT from 150
24 April 20261 May 20261 StopAmerican AirlinesRT from 149
27 April 202628 April 2026DirectSpirit AirlinesRT from 178
30 April 20263 May 20261 StopAllegiant AirRT from 252
20 May 202627 May 20261 StopSpirit AirlinesRT from 244
1 June 20267 June 20261 StopSpirit AirlinesRT from 275
4 June 20267 June 20261 StopAmerican AirlinesRT from 254
13 July 202623 July 20261 StopSpirit AirlinesRT from 309
20 July 202626 July 2026DirectFrontier AirlinesRT from 325
28 August 202622 September 20261 StopAmerican AirlinesRT from 348
20 September 202630 September 20262 StopsJetBlue AirwaysRT from 444
26 November 202630 November 20261 StopAmerican AirlinesRT from 644
19 December 20263 January 2027DirectAmerican AirlinesRT from 1 127
27 December 20261 January 20271 StopAmerican AirlinesRT from 873

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

Departure atReturn atStopsAirlineFind tickets
24 February 20266 March 2026DirectSpirit AirlinesRT from 172
2 March 20266 March 2026DirectSpirit AirlinesRT from 167
24 April 20261 May 20261 StopAmerican AirlinesRT from 149
20 May 202627 May 20261 StopSpirit AirlinesRT from 244
4 June 20267 June 20261 StopAmerican AirlinesRT from 254
13 July 202623 July 20261 StopSpirit AirlinesRT from 309
28 August 202622 September 20261 StopAmerican AirlinesRT from 348
20 September 202630 September 20262 StopsJetBlue AirwaysRT from 444
26 November 202630 November 20261 StopAmerican AirlinesRT from 644
27 December 20261 January 20271 StopAmerican AirlinesRT from 873
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