Cheap Flights from CHI to SJU
The Cheapest Round-trip Tickets from Chicago to San Juan
| Departure at | Return at | Stops | Airline | Find tickets |
|---|---|---|---|---|
| 19 August 2026 | 25 August 2026 | Direct |  | RT from 146 |
The Cheapest Flights for this Month from Chicago to San Juan
| Departure at | Return at | Stops | Airline | Find tickets |
|---|---|---|---|---|
| 3 July 2026 | 7 July 2026 | 2 Stops |  | RT from 381 |
| 6 July 2026 | 9 July 2026 | Direct |  | RT from 330 |
| 9 July 2026 | 12 July 2026 | Direct |  | RT from 414 |
| 4 August 2026 | 10 August 2026 | 1 Stop | | RT from 363 |
| 5 August 2026 | 10 August 2026 | Direct | | RT from 310 |
| 6 August 2026 | 10 August 2026 | 1 Stop |  | RT from 318 |
| 7 August 2026 | 16 August 2026 | Direct | | RT from 327 |
| 9 August 2026 | 17 August 2026 | 1 Stop | | RT from 334 |
| 10 August 2026 | 13 August 2026 | 1 Stop | | RT from 260 |
| 18 August 2026 | 25 August 2026 | 1 Stop | | RT from 218 |
| 19 August 2026 | 25 August 2026 | 1 Stop | | RT from 146 |
| 28 August 2026 | 5 September 2026 | Direct | | RT from 147 |
The Cheapest Flights from Chicago to San Juan for the Year Ahead
| Departure at | Return at | Stops | Airline | Find tickets |
|---|---|---|---|---|
| 6 July 2026 | 9 July 2026 | Direct | | RT from 330 |
| 19 August 2026 | 25 August 2026 | 1 Stop | | RT from 146 |