Using the online timetable is an easy way to look at all the direct flights San Diego — Chicago
114 flights in a week
Departure and arrival times are local (San Diego and Chicago)
| Departure | Arrival | Flight days | Flight | Airlines | Flight time | Airports | |
|---|---|---|---|---|---|---|---|
| 06:15 | 12:40 | daily | AA1494 | American Airlines | 4h 25m | San Diego International Airport — O'Hare International Airport | Select dates |
| 06:20 | 12:29 | wed | AA1494 | American Airlines | 4h 9m | San Diego International Airport — O'Hare International Airport | Select dates |
| 06:25 | 12:25 | mon, tue, wed, thu | WN1209 | Southwest Airlines | 4h 0m | San Diego International Airport — Chicago Midway International Airport | Select dates |
| 06:30 | 12:35 | wed, thu | WN4602 | Southwest Airlines | 4h 5m | San Diego International Airport — Chicago Midway International Airport | Select dates |
| 06:45 | 12:40 | thu | WN1209 | Southwest Airlines | 3h 55m | San Diego International Airport — Chicago Midway International Airport | Select dates |
| 07:00 | 13:13 | daily | UA2343 | United Airlines | 4h 13m | San Diego International Airport — O'Hare International Airport | Select dates |
| 07:25 | 13:20 | sat | WN1209 | Southwest Airlines | 3h 55m | San Diego International Airport — Chicago Midway International Airport | Select dates |
| 08:00 | 14:29 | fri | AS1495 | Alaska Horizon | 4h 29m | San Diego International Airport — O'Hare International Airport | Select dates |
| 08:05 | 14:37 | mon, tue, wed, thu, fri, sun | AS1446 | Alaska Horizon | 4h 32m | San Diego International Airport — O'Hare International Airport | Select dates |
| 08:25 | 14:57 | sat | AS1446 | Alaska Horizon | 4h 32m | San Diego International Airport — O'Hare International Airport | Select dates |
| 10:05 | 16:05 | mon, tue, wed | WN1934 | Southwest Airlines | 4h 0m | San Diego International Airport — Chicago Midway International Airport | Select dates |
| 10:35 | 16:30 | sat | WN3403 | Southwest Airlines | 3h 55m | San Diego International Airport — Chicago Midway International Airport | Select dates |
| 10:51 | 17:05 | daily | UA2677 | United Airlines | 4h 14m | San Diego International Airport — O'Hare International Airport | Select dates |
| 10:52 | 17:03 | fri, sat, sun | UA2677 | United Airlines | 4h 11m | San Diego International Airport — O'Hare International Airport | Select dates |
| 10:52 | 17:05 | fri | UA1710 | United Airlines | 4h 13m | San Diego International Airport — O'Hare International Airport | Select dates |
| 10:56 | 17:09 | thu, fri, sat, sun | UA1748 | United Airlines | 4h 13m | San Diego International Airport — O'Hare International Airport | Select dates |
| 12:20 | 18:25 | mon | WN3683 | Southwest Airlines | 4h 5m | San Diego International Airport — Chicago Midway International Airport | Select dates |
| 12:55 | 18:55 | mon, tue, fri, sun | WN1748 | Southwest Airlines | 4h 0m | San Diego International Airport — Chicago Midway International Airport | Select dates |
| 13:13 | 19:45 | mon, thu, fri | AA2131 | American Airlines | 4h 32m | San Diego International Airport — O'Hare International Airport | Select dates |
| 13:25 | 19:25 | sat | WN1748 | Southwest Airlines | 4h 0m | San Diego International Airport — Chicago Midway International Airport | Select dates |
| 13:58 | 20:15 | mon, tue, wed, thu, sun | AA2131 | American Airlines | 4h 17m | San Diego International Airport — O'Hare International Airport | Select dates |
| 14:01 | 20:15 | sat | AA2131 | American Airlines | 4h 14m | San Diego International Airport — O'Hare International Airport | Select dates |
| 14:11 | 20:25 | daily | UA1779 | United Airlines | 4h 14m | San Diego International Airport — O'Hare International Airport | Select dates |
| 15:02 | 21:15 | fri | AA2131 | American Airlines | 4h 13m | San Diego International Airport — O'Hare International Airport | Select dates |
| 15:03 | 21:30 | daily | AA2065 | American Airlines | 4h 27m | San Diego International Airport — O'Hare International Airport | Select dates |
| 15:06 | 21:25 | mon, thu, fri, sun | AA1861 | American Airlines | 4h 19m | San Diego International Airport — O'Hare International Airport | Select dates |
| 16:45 | 22:57 | mon, wed, fri, sun | UA2486 | United Airlines | 4h 12m | San Diego International Airport — O'Hare International Airport | Select dates |
| 17:00 | 22:55 | wed, thu | WN3683 | Southwest Airlines | 3h 55m | San Diego International Airport — Chicago Midway International Airport | Select dates |
| 17:10 | 23:37 | wed, sat | AS1493 | Alaska Horizon | 4h 27m | San Diego International Airport — O'Hare International Airport | Select dates |
| 17:31 | 23:59 | mon, fri, sun | AS1493 | Alaska Horizon | 4h 28m | San Diego International Airport — O'Hare International Airport | Select dates |
| 18:30 | 00:25 | mon, sat | WN1934 | Southwest Airlines | 3h 55m | San Diego International Airport — Chicago Midway International Airport | Select dates |
| 18:45 | 00:40 | sat | WN4602 | Southwest Airlines | 3h 55m | San Diego International Airport — Chicago Midway International Airport | Select dates |
| 19:00 | 00:55 | mon, tue, fri, sat, sun | WN4602 | Southwest Airlines | 3h 55m | San Diego International Airport — Chicago Midway International Airport | Select dates |
| 19:35 | 01:30 | mon, tue | WN4602 | Southwest Airlines | 3h 55m | San Diego International Airport — Chicago Midway International Airport | Select dates |
| 22:15 | 04:20 | sun | QR8596 | Qatar Airways (25 Years of Excellence Sticker) | 4h 5m | San Diego International Airport — O'Hare International Airport | Select dates |
| 22:30 | 04:38 | daily | UA2624 | United Airlines | 4h 8m | San Diego International Airport — O'Hare International Airport | Select dates |
| 22:55 | 05:00 | sat | QR8596 | Qatar Airways (25 Years of Excellence Sticker) | 4h 5m | San Diego International Airport — O'Hare International Airport | Select dates |