Using the online timetable is an easy way to look at all the direct flights San Diego — Chicago
109 flights in a week
Departure and arrival times are local (San Diego and Chicago)
| Departure | Arrival | Flight days | Flight | Airlines | Flight time | Airports | |
|---|---|---|---|---|---|---|---|
| 06:20 | 12:39 | daily | AA1494 | American Eagle | 4h 19m | San Diego International Airport — O'Hare International Airport | Select dates |
| 06:30 | 12:35 | tue, wed | WN2709 | Southwest Airlines | 4h 5m | San Diego International Airport — Chicago Midway International Airport | Select dates |
| 06:45 | 12:45 | mon, thu, fri, sat | WN2709 | Southwest Airlines | 4h 0m | San Diego International Airport — Chicago Midway International Airport | Select dates |
| 07:00 | 13:15 | daily | UA2343 | United Express | 4h 15m | San Diego International Airport — O'Hare International Airport | Select dates |
| 07:05 | 13:05 | sun | WN2819 | Southwest Airlines | 4h 0m | San Diego International Airport — Chicago Midway International Airport | Select dates |
| 07:55 | 14:21 | sun | AS1495 | Alaska Airlines | 4h 26m | San Diego International Airport — O'Hare International Airport | Select dates |
| 08:35 | 14:58 | daily | AS1495 | Alaska Airlines | 4h 23m | San Diego International Airport — O'Hare International Airport | Select dates |
| 10:05 | 16:05 | tue, wed | WN1934 | Southwest Airlines | 4h 0m | San Diego International Airport — Chicago Midway International Airport | Select dates |
| 10:50 | 16:45 | tue, wed | WN4363 | Southwest Airlines | 3h 55m | San Diego International Airport — Chicago Midway International Airport | Select dates |
| 10:59 | 17:05 | mon, tue, wed, thu, fri | UA1710 | United Express | 4h 6m | San Diego International Airport — O'Hare International Airport | Select dates |
| 11:03 | 17:05 | tue, thu, sat | UA1710 | United Express | 4h 2m | San Diego International Airport — O'Hare International Airport | Select dates |
| 11:05 | 17:00 | sun | WN3068 | Southwest Airlines | 3h 55m | San Diego International Airport — Chicago Midway International Airport | Select dates |
| 11:45 | 17:40 | sat | WN3910 | Southwest Airlines | 3h 55m | San Diego International Airport — Chicago Midway International Airport | Select dates |
| 12:10 | 18:05 | mon, thu, fri | WN3910 | Southwest Airlines | 3h 55m | San Diego International Airport — Chicago Midway International Airport | Select dates |
| 12:15 | 18:40 | tue | AS1459 | Alaska Airlines | 4h 25m | San Diego International Airport — O'Hare International Airport | Select dates |
| 12:37 | 19:02 | mon, wed, sun | AS1452 | Alaska Airlines | 4h 25m | San Diego International Airport — O'Hare International Airport | Select dates |
| 13:34 | 19:51 | mon, tue, fri, sat, sun | AA2131 | American Eagle | 4h 17m | San Diego International Airport — O'Hare International Airport | Select dates |
| 14:11 | 20:20 | daily | UA1779 | United Express | 4h 9m | San Diego International Airport — O'Hare International Airport | Select dates |
| 14:19 | 20:09 | mon | UA1779 | United Express | 3h 50m | North Island NAS — O'Hare International Airport | Select dates |
| 15:19 | 21:36 | mon, tue, wed, thu, fri, sun | AA2784 | American Eagle | 4h 17m | San Diego International Airport — O'Hare International Airport | Select dates |
| 16:45 | 22:35 | mon, thu, fri | WN4363 | Southwest Airlines | 3h 50m | San Diego International Airport — Chicago Midway International Airport | Select dates |
| 16:59 | 22:59 | mon, tue, wed, fri | UA2486 | United Express | 4h 0m | San Diego International Airport — O'Hare International Airport | Select dates |
| 16:59 | 23:00 | sat, sun | UA2486 | United Express | 4h 1m | San Diego International Airport — O'Hare International Airport | Select dates |
| 17:00 | 22:59 | mon, thu, fri, sun | UA2486 | United Express | 3h 59m | San Diego International Airport — O'Hare International Airport | Select dates |
| 17:00 | 23:00 | tue, wed, sat | UA2486 | United Express | 4h 0m | San Diego International Airport — O'Hare International Airport | Select dates |
| 17:02 | 22:21 | tue | UA2486 | United Express | 3h 18m | North Island NAS — O'Hare International Airport | Select dates |
| 17:38 | 23:59 | mon, thu, fri, sun | AS1493 | Alaska Airlines | 4h 21m | San Diego International Airport — O'Hare International Airport | Select dates |
| 18:30 | 00:25 | tue | WN1934 | Southwest Airlines | 3h 55m | San Diego International Airport — Chicago Midway International Airport | Select dates |
| 22:30 | 04:29 | wed, thu, fri, sat, sun | UA1457 | United Express | 3h 59m | San Diego International Airport — O'Hare International Airport | Select dates |
| 22:35 | 04:39 | daily | AA909 | American Eagle | 4h 4m | San Diego International Airport — O'Hare International Airport | Select dates |
| 22:40 | 04:35 | mon, tue, wed, fri, sat, sun | WN990 | Southwest Airlines | 3h 55m | San Diego International Airport — Chicago Midway International Airport | Select dates |