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 | |
|---|---|---|---|---|---|---|---|
| 06:15 | 12:40 | daily | AA1494 | American Airlines | 4h 25m | San Diego International Airport — O'Hare 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 |
| 06:35 | 12:40 | mon, tue, thu, fri, sun | WN2153 | Southwest Airlines | 4h 5m | San Diego International Airport — Chicago Midway International Airport | Select dates |
| 07:00 | 13:00 | sat | WN3768 | Southwest Airlines | 4h 0m | 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 |
| 07:00 | 13:11 | mon, tue, wed | UA2343 | United Airlines | 4h 11m | San Diego International Airport — O'Hare International Airport | Select dates |
| 07:10 | 13:10 | sat | WN2153 | Southwest Airlines | 4h 0m | 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 |
| 10:56 | 17:09 | thu, fri, sat, sun | UA1748 | United Airlines | 4h 13m | San Diego International Airport — O'Hare International Airport | Select dates |
| 11:00 | 17:00 | mon, tue, wed, thu, fri | WN3768 | Southwest Airlines | 4h 0m | San Diego International Airport — Chicago Midway International Airport | Select dates |
| 12:20 | 18:59 | mon, tue, wed, thu, fri, sun | AS1186 | Alaska Airlines (West Coast Wonders Livery) | 4h 39m | San Diego International Airport — O'Hare 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 | AA2131 | American Airlines | 4h 32m | San Diego International Airport — O'Hare International Airport | Select dates |
| 13:22 | 19:43 | sun | AA2131 | American Airlines | 4h 21m | San Diego International Airport — O'Hare International Airport | Select dates |
| 13:23 | 19:44 | mon, thu, sun | AA2131 | American Airlines | 4h 21m | San Diego International Airport — O'Hare International Airport | Select dates |
| 13:25 | 19:46 | tue, wed | AA2131 | American Airlines | 4h 21m | 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 |
| 13:30 | 20:02 | mon | AS1478 | Alaska Airlines (West Coast Wonders Livery) | 4h 32m | San Diego International Airport — O'Hare International Airport | Select dates |
| 13:41 | 19:55 | daily | AS1478 | Alaska Airlines (West Coast Wonders Livery) | 4h 14m | San Diego International Airport — O'Hare International Airport | Select dates |
| 13:45 | 19:54 | sun | AS1478 | Alaska Airlines (West Coast Wonders Livery) | 4h 9m | 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 |
| 15:03 | 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 |
| 17:00 | 22:55 | wed, thu | WN3683 | Southwest Airlines | 3h 55m | San Diego International Airport — Chicago Midway International Airport | Select dates |
| 18:45 | 00:40 | sat, sun | 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 | thu | WN4602 | Southwest Airlines | 3h 55m | San Diego International Airport — Chicago Midway International Airport | Select dates |
| 22:15 | 04:20 | sun | QR8596 | Qatar Airways | 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 | 4h 5m | San Diego International Airport — O'Hare International Airport | Select dates |