Using the online timetable is an easy way to look at all the direct flights San Antonio — Chicago
87 flights in a week
Departure and arrival times are local (San Antonio and Chicago)
| Departure | Arrival | Flight days | Flight | Airlines | Flight time | Airports | |
|---|---|---|---|---|---|---|---|
| 05:10 | 07:50 | mon, thu, fri | WN1598 | Southwest Airlines | 2h 40m | San Antonio International Airport — Chicago Midway International Airport | Select dates |
| 05:25 | 08:05 | sun | WN1598 | Southwest Airlines | 2h 40m | San Antonio International Airport — Chicago Midway International Airport | Select dates |
| 05:30 | 08:10 | sat | WN1598 | Southwest Airlines | 2h 40m | San Antonio International Airport — Chicago Midway International Airport | Select dates |
| 05:50 | 08:25 | mon, thu, fri | WN1525 | Southwest Airlines | 2h 35m | San Antonio International Airport — Chicago Midway International Airport | Select dates |
| 06:00 | 08:53 | daily | AA632 | American Eagle | 2h 53m | San Antonio International Airport — O'Hare International Airport | Select dates |
| 06:00 | 08:55 | mon, tue, fri | AA632 | American Eagle | 2h 55m | San Antonio International Airport — O'Hare International Airport | Select dates |
| 06:30 | 09:05 | tue, wed | WN3169 | Southwest Airlines | 2h 35m | San Antonio International Airport — Chicago Midway International Airport | Select dates |
| 06:30 | 09:29 | mon, wed, thu, fri | UA2008 | United Express | 2h 59m | San Antonio International Airport — O'Hare International Airport | Select dates |
| 06:40 | 09:15 | sun | WN1525 | Southwest Airlines | 2h 35m | San Antonio International Airport — Chicago Midway International Airport | Select dates |
| 06:45 | 09:44 | daily | UA2629 | United Express | 2h 59m | San Antonio International Airport — O'Hare International Airport | Select dates |
| 11:50 | 14:25 | mon, thu, fri | WN4008 | Southwest Airlines | 2h 35m | San Antonio International Airport — Chicago Midway International Airport | Select dates |
| 12:55 | 15:53 | daily | UA1905 | United Express | 2h 58m | San Antonio International Airport — O'Hare International Airport | Select dates |
| 12:57 | 15:53 | tue, wed, sat, sun | UA1905 | United Express | 2h 56m | San Antonio International Airport — O'Hare International Airport | Select dates |
| 13:08 | 16:00 | thu, sun | AA2278 | American Eagle | 2h 52m | San Antonio International Airport — O'Hare International Airport | Select dates |
| 13:25 | 16:24 | mon, tue, wed, thu, fri, sun | AA2278 | American Eagle | 2h 59m | San Antonio International Airport — O'Hare International Airport | Select dates |
| 13:50 | 16:25 | sat | WN3169 | Southwest Airlines | 2h 35m | San Antonio International Airport — Chicago Midway International Airport | Select dates |
| 14:40 | 17:15 | tue, wed | WN1525 | Southwest Airlines | 2h 35m | San Antonio International Airport — Chicago Midway International Airport | Select dates |
| 14:42 | 17:38 | sat | AA2278 | American Eagle | 2h 56m | San Antonio International Airport — O'Hare International Airport | Select dates |
| 14:50 | 17:25 | mon, thu, fri | WN2245 | Southwest Airlines | 2h 35m | San Antonio International Airport — Chicago Midway International Airport | Select dates |
| 15:00 | 17:54 | wed, sat | AA2278 | American Eagle | 2h 54m | San Antonio International Airport — O'Hare International Airport | Select dates |
| 16:35 | 19:10 | sun | WN4340 | Southwest Airlines | 2h 35m | San Antonio International Airport — Chicago Midway International Airport | Select dates |
| 17:08 | 20:10 | mon | UA5869 | United Express | 3h 2m | San Antonio International Airport — O'Hare International Airport | Select dates |
| 17:20 | 20:25 | mon, thu, fri, sun | UA5869 | United Express | 3h 5m | San Antonio International Airport — O'Hare International Airport | Select dates |
| 17:35 | 20:15 | tue, wed | WN2587 | Southwest Airlines | 2h 40m | San Antonio International Airport — Chicago Midway International Airport | Select dates |
| 18:10 | 20:45 | sun | WN2914 | Southwest Airlines | 2h 35m | San Antonio International Airport — Chicago Midway International Airport | Select dates |
| 18:24 | 21:15 | mon, thu, fri, sun | AA2435 | American Eagle | 2h 51m | San Antonio International Airport — O'Hare International Airport | Select dates |
| 18:28 | 21:25 | mon, tue | AA2366 | American Eagle | 2h 57m | San Antonio International Airport — O'Hare International Airport | Select dates |
| 18:30 | 21:10 | mon, thu, fri | WN1413 | Southwest Airlines | 2h 40m | San Antonio International Airport — Chicago Midway International Airport | Select dates |
| 18:30 | 21:05 | sun | WN3169 | Southwest Airlines | 2h 35m | San Antonio International Airport — Chicago Midway International Airport | Select dates |
| 21:40 | 23:59 | mon | 5X783 | UPS | 2h 19m | San Antonio International Airport — Chicago Rockford International Airport | Select dates |
| 21:40 | 23:56 | tue, wed, thu | 5X783 | UPS | 2h 16m | San Antonio International Airport — Chicago Rockford International Airport | Select dates |
| 21:43 | 00:02 | wed | 5X783 | UPS | 2h 19m | San Antonio International Airport — Chicago Rockford International Airport | Select dates |