Using the online timetable is an easy way to look at all the direct flights San Diego — Chicago
189 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 | 12:12 | sat | AA518 | American Airlines | 3h 57m | San Diego International Airport — O'Hare International Airport | Select dates |
| 06:15 | 12:29 | mon, fri, sat, sun | AA518 | American Airlines | 4h 14m | San Diego International Airport — O'Hare International Airport | Select dates |
| 06:15 | 12:31 | sat | AA518 | American Airlines | 4h 16m | San Diego International Airport — O'Hare International Airport | Select dates |
| 06:18 | 12:33 | daily | AA518 | American Airlines | 4h 15m | San Diego International Airport — O'Hare International Airport | Select dates |
| 06:20 | 12:10 | sat | WN770 | Southwest Airlines | 3h 50m | San Diego International Airport — Chicago Midway International Airport | Select dates |
| 06:30 | 12:30 | mon, thu, fri | WN1169 | Southwest Airlines | 4h 0m | San Diego International Airport — Chicago Midway International Airport | Select dates |
| 07:00 | 13:11 | tue, wed | UA1502 | United Airlines | 4h 11m | San Diego International Airport — O'Hare International Airport | Select dates |
| 07:00 | 13:04 | sat | UA1502 | United Airlines | 4h 4m | San Diego International Airport — O'Hare International Airport | Select dates |
| 07:00 | 13:13 | mon, tue, wed, thu, fri, sun | UA2343 | United Airlines | 4h 13m | San Diego International Airport — O'Hare International Airport | Select dates |
| 07:09 | 13:13 | daily | UA1502 | United Airlines | 4h 4m | San Diego International Airport — O'Hare International Airport | Select dates |
| 07:30 | 13:25 | tue | WN3045 | Southwest Airlines | 3h 55m | San Diego International Airport — Chicago Midway International Airport | Select dates |
| 07:35 | 13:30 | tue, wed | WN1428 | Southwest Airlines | 3h 55m | San Diego International Airport — Chicago Midway International Airport | Select dates |
| 07:40 | 13:35 | sun | WN3756 | Southwest Airlines | 3h 55m | San Diego International Airport — Chicago Midway International Airport | Select dates |
| 07:55 | 13:50 | sat | WN233 | Southwest Airlines | 3h 55m | San Diego International Airport — Chicago Midway International Airport | Select dates |
| 09:59 | 16:05 | sat | AA2131 | American Airlines | 4h 6m | San Diego International Airport — O'Hare International Airport | Select dates |
| 10:00 | 15:50 | wed | UA3887 | United Airlines | 3h 50m | San Diego International Airport — O'Hare International Airport | Select dates |
| 10:19 | 16:37 | mon, wed | AA2131 | American Airlines | 4h 18m | San Diego International Airport — O'Hare International Airport | Select dates |
| 10:27 | 16:41 | tue, wed, thu | AA2131 | American Airlines | 4h 14m | San Diego International Airport — O'Hare International Airport | Select dates |
| 10:59 | 17:10 | mon, tue, wed, thu, fri, sun | UA1633 | United Airlines | 4h 11m | San Diego International Airport — O'Hare International Airport | Select dates |
| 11:10 | 17:05 | tue, wed | WN770 | Southwest Airlines | 3h 55m | San Diego International Airport — Chicago Midway International Airport | Select dates |
| 11:10 | 17:10 | daily | UA519 | United Airlines | 4h 0m | San Diego International Airport — O'Hare International Airport | Select dates |
| 11:15 | 17:15 | mon, thu, fri, sat | WN1428 | Southwest Airlines | 4h 0m | San Diego International Airport — Chicago Midway International Airport | Select dates |
| 12:15 | 18:10 | sat | WN3045 | Southwest Airlines | 3h 55m | San Diego International Airport — Chicago Midway International Airport | Select dates |
| 13:10 | 19:10 | sat | WN2138 | Southwest Airlines | 4h 0m | San Diego International Airport — Chicago Midway International Airport | Select dates |
| 13:20 | 19:15 | thu, fri, sun | WN1506 | Southwest Airlines | 3h 55m | San Diego International Airport — Chicago Midway International Airport | Select dates |
| 13:28 | 19:38 | mon, tue, wed, sun | AA2131 | American Airlines | 4h 10m | San Diego International Airport — O'Hare International Airport | Select dates |
| 13:30 | 19:35 | mon, thu, fri, sun | AA2131 | American Airlines | 4h 5m | San Diego International Airport — O'Hare International Airport | Select dates |
| 13:30 | 19:37 | wed, thu, sat | AA2131 | American Airlines | 4h 7m | San Diego International Airport — O'Hare International Airport | Select dates |
| 13:34 | 19:38 | tue, wed, sat | AA2131 | American Airlines | 4h 4m | San Diego International Airport — O'Hare International Airport | Select dates |
| 13:35 | 19:30 | sun | WN3045 | Southwest Airlines | 3h 55m | San Diego International Airport — Chicago Midway International Airport | Select dates |
| 13:50 | 19:50 | sun | WN1428 | Southwest Airlines | 4h 0m | San Diego International Airport — Chicago Midway International Airport | Select dates |
| 14:10 | 20:18 | daily | UA2491 | United Airlines | 4h 8m | San Diego International Airport — O'Hare International Airport | Select dates |
| 14:23 | 20:25 | wed, thu, fri, sat | UA2059 | United Airlines | 4h 2m | San Diego International Airport — O'Hare International Airport | Select dates |
| 14:45 | 20:40 | wed | WN3997 | Southwest Airlines | 3h 55m | San Diego International Airport — Chicago Midway International Airport | Select dates |
| 14:49 | 21:06 | daily | AA1461 | American Airlines | 4h 17m | San Diego International Airport — O'Hare International Airport | Select dates |
| 15:04 | 21:12 | daily | AA2189 | American Airlines | 4h 8m | San Diego International Airport — O'Hare International Airport | Select dates |
| 16:40 | 22:45 | daily | UA2486 | United Airlines | 4h 5m | San Diego International Airport — O'Hare International Airport | Select dates |
| 16:45 | 22:52 | daily | UA2486 | United Airlines | 4h 7m | San Diego International Airport — O'Hare International Airport | Select dates |
| 16:46 | 22:45 | mon, thu, fri, sun | UA1302 | United Airlines | 3h 59m | San Diego International Airport — O'Hare International Airport | Select dates |
| 16:50 | 22:40 | mon, tue, wed, thu, fri, sun | WN1506 | Southwest Airlines | 3h 50m | San Diego International Airport — Chicago Midway International Airport | Select dates |
| 16:55 | 22:59 | thu | UA2486 | United Airlines | 4h 4m | San Diego International Airport — O'Hare International Airport | Select dates |
| 16:55 | 22:58 | daily | UA2486 | United Airlines | 4h 3m | San Diego International Airport — O'Hare International Airport | Select dates |
| 17:05 | 23:09 | fri | UA2486 | United Airlines | 4h 4m | San Diego International Airport — O'Hare International Airport | Select dates |
| 17:10 | 23:00 | wed | WN1506 | Southwest Airlines | 3h 50m | San Diego International Airport — Chicago Midway International Airport | Select dates |
| 17:15 | 23:05 | mon, thu, fri, sun | WN1506 | Southwest Airlines | 3h 50m | San Diego International Airport — Chicago Midway International Airport | Select dates |
| 17:25 | 23:04 | wed | DL8887 | Delta Air Lines | 3h 39m | San Diego International Airport — O'Hare International Airport | Select dates |
| 17:30 | 23:20 | mon | WN1506 | Southwest Airlines | 3h 50m | San Diego International Airport — Chicago Midway International Airport | Select dates |
| 17:40 | 23:30 | sat | WN3997 | Southwest Airlines | 3h 50m | San Diego International Airport — Chicago Midway International Airport | Select dates |
| 17:55 | 23:55 | mon, tue, wed, thu, fri | WN495 | Southwest Airlines | 4h 0m | San Diego International Airport — Chicago Midway International Airport | Select dates |
| 18:55 | 00:50 | tue, fri, sat | WN3997 | Southwest Airlines | 3h 55m | San Diego International Airport — Chicago Midway International Airport | Select dates |
| 19:40 | 01:35 | mon | WN3997 | Southwest Airlines | 3h 55m | San Diego International Airport — Chicago Midway International Airport | Select dates |
| 19:55 | 01:50 | mon | WN2876 | Southwest Airlines | 3h 55m | San Diego International Airport — Chicago Midway International Airport | Select dates |
| 22:10 | 04:17 | daily | UA2352 | United Airlines | 4h 7m | San Diego International Airport — O'Hare International Airport | Select dates |
| 22:30 | 04:40 | thu, fri, sat | UA2633 | United Airlines | 4h 10m | San Diego International Airport — O'Hare International Airport | Select dates |
| 22:33 | 04:38 | sun | AA2065 | American Airlines | 4h 5m | San Diego International Airport — O'Hare International Airport | Select dates |
| 22:37 | 05:22 | sun | AA2985 | American Airlines | 3h 45m | San Diego International Airport — O'Hare International Airport | Select dates |
| 22:39 | 04:42 | mon, fri, sat, sun | AA2985 | American Airlines | 4h 3m | San Diego International Airport — O'Hare International Airport | Select dates |
| 22:39 | 04:47 | daily | AA2065 | American Airlines | 4h 8m | San Diego International Airport — O'Hare International Airport | Select dates |
| 22:45 | 04:30 | mon, tue, fri, sat | AA2985 | American Airlines | 3h 45m | San Diego International Airport — O'Hare International Airport | Select dates |