Cheap Flights from CHI to SJU
The Cheapest Round-trip Tickets from Chicago to San Juan
| Departure at | Return at | Stops | Airline | Find tickets |
|---|---|---|---|---|
| 12 December 2026 | 18 December 2026 | Direct |  | RT from 188 USD |
The Cheapest Flights for this Month from Chicago to San Juan
| Departure at | Return at | Stops | Airline | Find tickets |
|---|---|---|---|---|
| 9 October 2026 | 19 October 2026 | 1 Stop | | RT from 257 USD |
| 13 October 2026 | 22 October 2026 | 1 Stop | | RT from 238 USD |
| 16 October 2026 | 18 October 2026 | 1 Stop | | RT from 343 USD |
| 23 October 2026 | 25 October 2026 | 1 Stop |  | RT from 334 USD |
| 1 November 2026 | 9 November 2026 | 2 Stops | | RT from 268 USD |
| 2 November 2026 | 8 November 2026 | 1 Stop | | RT from 216 USD |
| 6 November 2026 | 8 November 2026 | 1 Stop | | RT from 303 USD |
| 12 November 2026 | 12 November 2026 | 1 Stop |  | RT from 403 USD |
| 22 November 2026 | 28 November 2026 | 1 Stop | | RT from 457 USD |
| 4 December 2026 | 13 December 2026 | 1 Stop | | RT from 211 USD |
| 6 December 2026 | 13 December 2026 | 1 Stop | | RT from 206 USD |
| 12 December 2026 | 18 December 2026 | 1 Stop | | RT from 188 USD |
| 24 December 2026 | 28 December 2026 | 1 Stop | | RT from 420 USD |
| 30 December 2026 | 4 January 2027 | 1 Stop | | RT from 515 USD |
| 10 January 2027 | 17 January 2027 | 1 Stop |  | RT from 340 USD |
| 1 June 2027 | 6 June 2027 | Direct | | RT from 308 USD |
The Cheapest Flights from Chicago to San Juan for the Year Ahead
| Departure at | Return at | Stops | Airline | Find tickets |
|---|---|---|---|---|
| 13 October 2026 | 22 October 2026 | 1 Stop | | RT from 238 USD |
| 2 November 2026 | 8 November 2026 | 1 Stop | | RT from 216 USD |
| 12 December 2026 | 18 December 2026 | 1 Stop | | RT from 188 USD |
| 10 January 2027 | 17 January 2027 | 1 Stop | | RT from 340 USD |
| 1 June 2027 | 6 June 2027 | Direct | | RT from 308 USD |