Utilizar el calendario en línea es una manera fácil de ver todos los vuelos directos desde San Juan a Chicago
72 vuelos en una semana
Los horarios de salida y llegada son locales (San Juan — Chicago)
| Salida | Llegada | Días de vuelo | Vuelo | Aerolíneas | Tiempo de vuelo | Aeropuertos | |
|---|---|---|---|---|---|---|---|
| 06:00 | 09:29 | diario | AA1869 | American Airlines | 5h 29m | Luis Munoz Marin — O'Hare International | Seleccionar fechas |
| 06:00 | 09:35 | lu, sá, do | AA1540 | American Airlines | 5h 35m | Luis Munoz Marin — O'Hare International | Seleccionar fechas |
| 08:10 | 11:32 | diario | UA2089 | United Express | 5h 22m | Luis Munoz Marin — O'Hare International | Seleccionar fechas |
| 08:35 | 11:57 | diario | UA2089 | United Express | 5h 22m | Luis Munoz Marin — O'Hare International | Seleccionar fechas |
| 12:00 | 15:12 | do | NetJets | 5h 12m | Luis Munoz Marin — Midway | Seleccionar fechas | |
| 13:22 | 16:37 | vi | NK2208 | Spirit Airlines | 5h 15m | Luis Munoz Marin — O'Hare International | Seleccionar fechas |
| 14:20 | 17:35 | sá | WN204 | Southwest Airlines | 5h 15m | Luis Munoz Marin — Midway | Seleccionar fechas |
| 15:00 | 20:57 | mi | American Airlines | 6h 57m | Luis Munoz Marin — O'Hare International | Seleccionar fechas | |
| 15:00 | 18:20 | sá | WN2952 | Southwest Airlines | 5h 20m | Luis Munoz Marin — Midway | Seleccionar fechas |
| 15:38 | 19:10 | sá | AA3276 | American Airlines | 5h 32m | Luis Munoz Marin — O'Hare International | Seleccionar fechas |
| 15:41 | 18:51 | lu, vi | NK3032 | Spirit Airlines | 5h 10m | Luis Munoz Marin — O'Hare International | Seleccionar fechas |
| 15:43 | 19:21 | lu, ju, do | AA2865 | American Airlines | 5h 38m | Luis Munoz Marin — O'Hare International | Seleccionar fechas |
| 15:50 | 19:10 | sá | WN910 | Southwest Airlines | 5h 20m | Luis Munoz Marin — Midway | Seleccionar fechas |
| 15:53 | 19:12 | ju, vi, sá, do | AA3074 | American Airlines | 5h 19m | Luis Munoz Marin — O'Hare International | Seleccionar fechas |
| 15:58 | 19:34 | diario | AA3276 | American Airlines | 5h 36m | Luis Munoz Marin — O'Hare International | Seleccionar fechas |
| 16:02 | 19:37 | mi | AA3276 | American Airlines | 5h 35m | Luis Munoz Marin — O'Hare International | Seleccionar fechas |
| 16:28 | 20:00 | lu, ma, ju | AA3276 | American Airlines | 5h 32m | Luis Munoz Marin — O'Hare International | Seleccionar fechas |
| 16:52 | 20:20 | diario | UA2088 | United Express | 5h 28m | Luis Munoz Marin — O'Hare International | Seleccionar fechas |
| 17:00 | 20:30 | mi | NetJets | 5h 30m | Luis Munoz Marin — O'Hare International | Seleccionar fechas | |
| 19:31 | 22:53 | ma, mi, sá | NK1480 | Spirit Airlines | 5h 22m | Luis Munoz Marin — O'Hare International | Seleccionar fechas |
| 20:08 | 23:25 | lu, mi, vi, sá, do | NK1480 | Spirit Airlines | 5h 17m | Luis Munoz Marin — O'Hare International | Seleccionar fechas |
| 20:45 | 23:59 | lu, ju, vi, do | NK1480 | Spirit Airlines | 5h 14m | Luis Munoz Marin — O'Hare International | Seleccionar fechas |
| 22:47 | 01:44 | sá | 5X7981 | UPS | 4h 57m | Luis Munoz Marin — O'Hare International | Seleccionar fechas |