Using the online timetable is an easy way to look at all the direct flights San Juan — Chicago
48 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 | 09:29 | mon, fri, sat, sun | AA1869 | American Airlines | 5h 29m | Luis Munoz Marin International Airport — O'Hare International Airport | Select dates |
| 08:10 | 11:32 | daily | UA2089 | United Airlines | 5h 22m | 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 | |
| 14:20 | 17:35 | sat | WN204 | Southwest Airlines | 5h 15m | Luis Munoz Marin International Airport — Chicago Midway International Airport | Select dates |
| 15:00 | 20:57 | wed | American Airlines | 6h 57m | Luis Munoz Marin International Airport — O'Hare International Airport | Select dates | |
| 15:41 | 18:51 | mon, fri | NK3032 | Spirit Airlines | 5h 10m | Luis Munoz Marin International Airport — O'Hare International Airport | Select dates |
| 15:43 | 19:21 | mon, thu, sun | AA2865 | American Airlines | 5h 38m | Luis Munoz Marin International Airport — O'Hare International Airport | Select dates |
| 15:50 | 19:10 | sat | WN910 | Southwest Airlines | 5h 20m | Luis Munoz Marin International Airport — Chicago Midway International Airport | Select dates |
| 15:52 | 20:20 | tue, thu, sun | UA2088 | United Airlines | 5h 28m | Luis Munoz Marin International Airport — O'Hare International Airport | Select dates |
| 15:53 | 19:12 | thu, fri, sat, sun | AA3074 | American Airlines | 5h 19m | Luis Munoz Marin International Airport — O'Hare International Airport | Select dates |
| 15:58 | 19:29 | sat, sun | AA3276 | American Airlines | 5h 31m | Luis Munoz Marin International Airport — O'Hare International Airport | Select dates |
| 15:58 | 19:34 | mon | AA3276 | American Airlines | 5h 36m | Luis Munoz Marin International Airport — O'Hare International Airport | Select dates |
| 16:52 | 20:20 | mon, tue, wed, fri, sat, sun | UA2088 | United Airlines | 5h 28m | 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 | |
| 19:31 | 22:53 | tue, wed, sat | NK1480 | Spirit Airlines | 5h 22m | Luis Munoz Marin International Airport — O'Hare International Airport | Select dates |
| 20:08 | 23:25 | fri, sat, sun | NK1480 | Spirit Airlines | 5h 17m | Luis Munoz Marin International Airport — O'Hare International Airport | Select dates |
| 20:45 | 23:59 | mon, thu, fri, sun | NK1480 | Spirit Airlines | 5h 14m | Luis Munoz Marin International Airport — O'Hare International Airport | Select dates |
| 22:47 | 01:44 | sat | 5X7981 | UPS | 4h 57m | Luis Munoz Marin International Airport — O'Hare International Airport | Select dates |