Using the online timetable is an easy way to look at all the direct flights San Diego — Chicago
202 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 | 12:31 | daily | AA518 | American Airlines | 4h 16m | 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 |
| 06:20 | 12:40 | tue, sun | AA518 | American Airlines | 4h 20m | San Diego International Airport — O'Hare 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 |
| 06:30 | 12:49 | daily | UA2343 | United Airlines | 4h 19m | San Diego International Airport — O'Hare International Airport | Select dates |
| 06:35 | 12:40 | sun | WN3176 | Southwest Airlines | 4h 5m | San Diego International Airport — Chicago Midway International Airport | Select dates |
| 07:00 | 13:13 | tue, wed | UA2343 | United Airlines | 4h 13m | San Diego International Airport — O'Hare International Airport | Select dates |
| 07:00 | 13:10 | fri | WN3152 | Southwest Airlines | 4h 10m | San Diego International Airport — Chicago Midway International Airport | Select dates |
| 07:20 | 13:25 | sat | WN2927 | Southwest Airlines | 4h 5m | San Diego International Airport — Chicago Midway 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 |
| 08:15 | 14:20 | tue, wed | WN3176 | Southwest Airlines | 4h 5m | San Diego International Airport — Chicago Midway International Airport | Select dates |
| 09:47 | 15:59 | fri | AA2343 | American Airlines | 4h 12m | San Diego International Airport — O'Hare 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, tue, wed, thu, sun | 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 |
| 10:33 | 16:48 | tue, wed, fri | AA2343 | American Airlines | 4h 15m | San Diego International Airport — O'Hare International Airport | Select dates |
| 10:46 | 17:05 | daily | UA2677 | United Airlines | 4h 19m | 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 |
| 11:20 | 17:20 | wed | WN2932 | Southwest Airlines | 4h 0m | San Diego International Airport — Chicago Midway International Airport | Select dates |
| 11:25 | 17:25 | thu | WN557 | Southwest Airlines | 4h 0m | San Diego International Airport — Chicago Midway International Airport | Select dates |
| 11:55 | 18:00 | sun | WN2921 | Southwest Airlines | 4h 5m | 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 |
| 12:25 | 18:20 | sun | WN3756 | Southwest Airlines | 3h 55m | San Diego International Airport — Chicago Midway International Airport | Select dates |
| 13:00 | 19:25 | tue, wed, fri | AA2131 | American Airlines | 4h 25m | San Diego International Airport — O'Hare International Airport | Select dates |
| 13:10 | 19:10 | sat | WN2138 | Southwest Airlines | 4h 0m | San Diego International Airport — Chicago Midway International Airport | Select dates |
| 13:28 | 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 |
| 13:58 | 20:13 | wed, sun | UA369 | United Airlines | 4h 15m | San Diego International Airport — O'Hare International Airport | Select dates |
| 14:04 | 20:19 | thu | UA369 | United Airlines | 4h 15m | San Diego International Airport — O'Hare International Airport | Select dates |
| 14:05 | 20:20 | fri, sat, sun | UA2628 | United Airlines | 4h 15m | San Diego International Airport — O'Hare International Airport | Select dates |
| 14:10 | 20:18 | daily | UA2491 | United Airlines | 4h 8m | San Diego International Airport — O'Hare International Airport | Select dates |
| 14:15 | 20:10 | tue, wed | WN2189 | Southwest Airlines | 3h 55m | San Diego International Airport — Chicago Midway International Airport | Select dates |
| 14:45 | 20:40 | wed | WN3997 | Southwest Airlines | 3h 55m | San Diego International Airport — Chicago Midway International Airport | Select dates |
| 14:54 | 21:11 | mon, tue, wed, thu, fri, sat | AA2309 | American Airlines | 4h 17m | San Diego International Airport — O'Hare International Airport | Select dates |
| 14:55 | 21:14 | sun | AA2309 | American Airlines | 4h 19m | San Diego International Airport — O'Hare International Airport | Select dates |
| 16:44 | 23:07 | daily | F91856 | Frontier (Nevada the Red Fox Livery) | 4h 23m | 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 |
| 16:53 | 22:56 | mon, tue, wed, thu, fri | F91856 | Frontier (Nevada the Red Fox Livery) | 4h 3m | San Diego International Airport — O'Hare International Airport | Select dates |
| 17:00 | 23:15 | daily | UA2486 | United Airlines | 4h 15m | San Diego International Airport — O'Hare 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 | 23:44 | mon, thu, fri | UA2486 | United Airlines | 4h 14m | San Diego International Airport — O'Hare International Airport | Select dates |
| 17:34 | 23:48 | sat | UA2486 | United Airlines | 4h 14m | San Diego International Airport — O'Hare International Airport | Select dates |
| 17:35 | 23:50 | thu | UA2486 | United Airlines | 4h 15m | San Diego International Airport — O'Hare International Airport | Select dates |
| 17:40 | 23:30 | sat | WN3997 | Southwest Airlines | 3h 50m | San Diego International Airport — Chicago Midway International Airport | Select dates |
| 17:45 | 23:45 | mon, thu, fri | WN3797 | Southwest Airlines | 4h 0m | 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, wed, thu, fri, sat | WN3797 | 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 |
| 22:20 | 04:30 | daily | UA2633 | United Airlines | 4h 10m | 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 |
| 22:38 | 04:45 | fri, sat | AA2065 | American Airlines | 4h 7m | 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 |
| 22:45 | 04:52 | daily | AA2065 | American Airlines | 4h 7m | San Diego International Airport — O'Hare International Airport | Select dates |
| 22:45 | 04:56 | sun | AA2065 | American Airlines | 4h 11m | San Diego International Airport — O'Hare International Airport | Select dates |