Using the online timetable is an easy way to look at all the direct flights San Juan — Chicago
85 flights in a week
Departure and arrival times are local (San Juan and Chicago)
| Departure | Arrival | Flight days | Flight | Airlines | Flight time | Airports | |
|---|---|---|---|---|---|---|---|
| 06:00 | 10:16 | mon, thu, fri, sat, sun | NK1632 | Spirit Airlines | 5h 16m | Luis Munoz Marin International Airport — O'Hare International Airport | Select dates |
| 06:50 | 11:06 | daily | NK2534 | Spirit Airlines | 5h 16m | Luis Munoz Marin International Airport — O'Hare International Airport | Select dates |
| 07:35 | 11:54 | tue, wed, thu, sat, sun | UA2089 | United Airlines | 5h 19m | Luis Munoz Marin International Airport — O'Hare International Airport | Select dates |
| 07:45 | 11:55 | daily | UA2089 | United Airlines | 5h 10m | Luis Munoz Marin International Airport — O'Hare International Airport | Select dates |
| 07:45 | 11:51 | tue | UA2089 | United Airlines | 5h 6m | Luis Munoz Marin International Airport — O'Hare International Airport | Select dates |
| 08:35 | 11:54 | sat, sun | UA2089 | United Airlines | 5h 19m | Luis Munoz Marin International Airport — O'Hare International Airport | Select dates |
| 09:44 | 13:58 | tue, wed | NK1632 | Spirit Airlines | 5h 14m | Luis Munoz Marin International Airport — O'Hare International Airport | Select dates |
| 12:00 | 15:12 | sun | NetJets | 5h 12m | Luis Munoz Marin International Airport — Chicago Midway International Airport | Select dates | |
| 12:55 | 17:25 | sun | WN1578 | Southwest Airlines | 5h 30m | Luis Munoz Marin International Airport — Chicago Midway International Airport | Select dates |
| 13:05 | 17:05 | sat | WN3887 | Southwest Airlines | 5h 0m | Luis Munoz Marin International Airport — Chicago Midway International Airport | Select dates |
| 13:39 | 17:50 | wed | NK2081 | Spirit Airlines | 5h 11m | Luis Munoz Marin International Airport — O'Hare International Airport | Select dates |
| 14:25 | 18:44 | sat | UA1045 | United Airlines | 5h 19m | Luis Munoz Marin International Airport — O'Hare International Airport | Select dates |
| 14:55 | 19:10 | daily | AA1184 | American Eagle | 5h 15m | Luis Munoz Marin International Airport — O'Hare International Airport | Select dates |
| 15:00 | 20:57 | wed | American Eagle | 6h 57m | Luis Munoz Marin International Airport — O'Hare International Airport | Select dates | |
| 15:15 | 19:20 | sun | WN3887 | Southwest Airlines | 5h 5m | Luis Munoz Marin International Airport — Chicago Midway International Airport | Select dates |
| 15:23 | 19:38 | daily | AA1184 | American Eagle | 5h 15m | Luis Munoz Marin International Airport — O'Hare International Airport | Select dates |
| 15:56 | 20:15 | daily | UA2088 | United Airlines | 5h 19m | Luis Munoz Marin International Airport — O'Hare International Airport | Select dates |
| 15:56 | 20:03 | mon, tue, sun | UA2088 | United Airlines | 5h 7m | Luis Munoz Marin International Airport — O'Hare International Airport | Select dates |
| 17:00 | 20:30 | wed | NetJets | 5h 30m | Luis Munoz Marin International Airport — O'Hare International Airport | Select dates | |
| 17:05 | 21:35 | sat | WN1578 | Southwest Airlines | 5h 30m | Luis Munoz Marin International Airport — Chicago Midway International Airport | Select dates |
| 18:05 | 21:35 | sat | WN1578 | Southwest Airlines | 5h 30m | Luis Munoz Marin International Airport — Chicago Midway International Airport | Select dates |
| 19:40 | 23:43 | mon, thu, sat, sun | NK2081 | Spirit Airlines | 5h 3m | Luis Munoz Marin International Airport — O'Hare International Airport | Select dates |
| 19:40 | 23:56 | mon, thu, fri, sun | NK2081 | Spirit Airlines | 5h 16m | Luis Munoz Marin International Airport — O'Hare International Airport | Select dates |
| 19:57 | 23:20 | tue, thu, sun | NK173 | Spirit Airlines | 5h 23m | Luis Munoz Marin International Airport — O'Hare International Airport | Select dates |
| 20:31 | 23:55 | mon, wed, fri, sat | NK173 | Spirit Airlines | 5h 24m | Luis Munoz Marin International Airport — O'Hare International Airport | Select dates |
| 21:26 | 00:51 | daily | NK173 | Spirit Airlines | 5h 25m | Luis Munoz Marin International Airport — O'Hare International Airport | Select dates |