Using the online timetable is an easy way to look at all the direct flights San Diego — Chicago
153 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 | 12:37 | daily | AA518 | American Airlines | 4h 22m | San Diego International Airport — O'Hare International Airport | Select dates |
| 06:15 | 12:42 | tue, wed, sat | AA518 | American Airlines | 4h 27m | San Diego International Airport — O'Hare International Airport | Select dates |
| 06:19 | 12:39 | tue, wed, sat | AA518 | American Airlines | 4h 20m | San Diego International Airport — O'Hare International Airport | Select dates |
| 06:35 | 12:40 | mon, thu, fri, sun | WN3752 | Southwest Airlines | 4h 5m | San Diego International Airport — Chicago Midway International Airport | Select dates |
| 06:40 | 12:59 | mon, thu, fri, sat, sun | UA2343 | United Airlines | 4h 19m | San Diego International Airport — O'Hare International Airport | Select dates |
| 06:55 | 12:55 | thu, fri, sun | WN202 | Southwest Airlines | 4h 0m | 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 | 13:30 | sat | WN594 | Southwest Airlines | 4h 0m | San Diego International Airport — Chicago Midway International Airport | Select dates |
| 08:00 | 13:55 | tue, wed | WN594 | Southwest Airlines | 3h 55m | San Diego International Airport — Chicago Midway International Airport | Select dates |
| 08:00 | 13:50 | fri | AS9686 | Alaska Airlines | 3h 50m | San Diego International Airport — Chicago Rockford International Airport | Select dates |
| 08:15 | 14:20 | wed | WN3176 | Southwest Airlines | 4h 5m | San Diego International Airport — Chicago Midway International Airport | Select dates |
| 10:10 | 16:36 | daily | AA2343 | American Airlines | 4h 26m | San Diego International Airport — O'Hare International Airport | Select dates |
| 10:15 | 16:39 | sat | AA2343 | American Airlines | 4h 24m | San Diego International Airport — O'Hare International Airport | Select dates |
| 10:40 | 16:40 | tue, wed | WN202 | Southwest Airlines | 4h 0m | San Diego International Airport — Chicago Midway International Airport | Select dates |
| 10:41 | 16:57 | sat | UA2677 | United Airlines | 4h 16m | San Diego International Airport — O'Hare International Airport | Select dates |
| 10:41 | 17:00 | mon, tue, sat | UA1712 | United Airlines | 4h 19m | San Diego International Airport — O'Hare International Airport | Select dates |
| 10:42 | 17:05 | fri | AA2343 | American Airlines | 4h 23m | San Diego International Airport — O'Hare International Airport | Select dates |
| 10:45 | 16:45 | sat | WN457 | Southwest Airlines | 4h 0m | San Diego International Airport — Chicago Midway International Airport | Select dates |
| 10:46 | 17:12 | daily | AA2343 | American Airlines | 4h 26m | San Diego International Airport — O'Hare International Airport | Select dates |
| 10:46 | 17:05 | fri | UA2677 | United Airlines | 4h 19m | San Diego International Airport — O'Hare International Airport | Select dates |
| 10:50 | 16:50 | sun | WN1697 | Southwest Airlines | 4h 0m | San Diego International Airport — Chicago Midway International Airport | Select dates |
| 11:00 | 17:00 | sun | WN1697 | Southwest Airlines | 4h 0m | San Diego International Airport — Chicago Midway International Airport | Select dates |
| 11:11 | 17:34 | wed | AA2343 | American Airlines | 4h 23m | San Diego International Airport — O'Hare International Airport | Select dates |
| 13:08 | 19:25 | mon, wed, sun | AA2131 | American Airlines | 4h 17m | San Diego International Airport — O'Hare International Airport | Select dates |
| 13:12 | 19:35 | daily | AA2131 | American Airlines | 4h 23m | San Diego International Airport — O'Hare International Airport | Select dates |
| 13:17 | 19:41 | mon, sat, sun | AA2131 | American Airlines | 4h 24m | San Diego International Airport — O'Hare International Airport | Select dates |
| 13:40 | 19:40 | mon, thu, fri | WN2206 | Southwest Airlines | 4h 0m | San Diego International Airport — Chicago Midway International Airport | Select dates |
| 13:50 | 19:50 | sun | WN457 | Southwest Airlines | 4h 0m | San Diego International Airport — Chicago Midway International Airport | Select dates |
| 14:05 | 20:20 | daily | UA2628 | United Airlines | 4h 15m | San Diego International Airport — O'Hare International Airport | Select dates |
| 14:11 | 20:25 | mon, tue, sat | UA1779 | United Airlines | 4h 14m | 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 |
| 14:50 | 21:09 | mon, tue | AA2309 | American Airlines | 4h 19m | San Diego International Airport — O'Hare International Airport | Select dates |
| 14:55 | 21:12 | daily | AA3311 | American Airlines | 4h 17m | San Diego International Airport — O'Hare International Airport | Select dates |
| 15:10 | 21:10 | sun | WN3797 | Southwest Airlines | 4h 0m | San Diego International Airport — Chicago Midway International Airport | Select dates |
| 15:40 | 22:03 | mon, thu, fri | F91856 | Frontier (Ozzy the Orca Livery) | 4h 23m | San Diego International Airport — O'Hare International Airport | Select dates |
| 16:05 | 22:00 | tue | WN457 | Southwest Airlines | 3h 55m | San Diego International Airport — Chicago Midway International Airport | Select dates |
| 16:05 | 22:28 | sun | F91856 | Frontier (Ozzy the Orca Livery) | 4h 23m | San Diego International Airport — O'Hare International Airport | Select dates |
| 16:25 | 22:07 | sun | DL8887 | Delta Air Lines | 3h 42m | San Diego International Airport — O'Hare International Airport | Select dates |
| 16:50 | 22:50 | sat | WN478 | Southwest Airlines | 4h 0m | San Diego International Airport — Chicago Midway International Airport | Select dates |
| 16:53 | 23:15 | thu | F91856 | Frontier (Ozzy the Orca Livery) | 4h 22m | San Diego International Airport — O'Hare International Airport | Select dates |
| 17:01 | 23:14 | daily | UA2486 | United Airlines | 4h 13m | San Diego International Airport — O'Hare International Airport | Select dates |
| 17:35 | 23:35 | sat | WN3797 | Southwest Airlines | 4h 0m | 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 |
| 17:45 | 23:45 | mon, thu, fri | WN3797 | Southwest Airlines | 4h 0m | San Diego International Airport — Chicago Midway International Airport | Select dates |
| 18:30 | 00:30 | mon, thu, fri | WN2053 | Southwest Airlines | 4h 0m | San Diego International Airport — Chicago Midway International Airport | Select dates |
| 18:55 | 00:50 | tue, wed, thu | 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 |
| 20:01 | 02:10 | sun | UA3751 | United Airlines | 4h 9m | San Diego International Airport — O'Hare International Airport | Select dates |
| 20:50 | 02:40 | fri | UA3930 | United Airlines | 3h 50m | San Diego International Airport — O'Hare International Airport | Select dates |
| 22:15 | 04:22 | mon | UA3762 | United Airlines | 4h 7m | San Diego International Airport — O'Hare International Airport | Select dates |
| 22:20 | 04:30 | daily | UA1726 | United Airlines | 4h 10m | San Diego International Airport — O'Hare International Airport | Select dates |
| 22:30 | 04:37 | daily | UA2624 | United Airlines | 4h 7m | San Diego International Airport — O'Hare International Airport | Select dates |
| 22:38 | 04:56 | mon, fri | AA2065 | American Airlines | 4h 18m | San Diego International Airport — O'Hare International Airport | Select dates |
| 22:45 | 04:56 | daily | AA2065 | American Airlines | 4h 11m | San Diego International Airport — O'Hare International Airport | Select dates |
| 22:45 | 04:54 | mon, tue, fri, sat | AA2065 | American Airlines | 4h 9m | San Diego International Airport — O'Hare International Airport | Select dates |