Using the online timetable is an easy way to look at all the direct flights San Jose — Chicago
28 flights in a week
Departure and arrival times are local (San Jose and Chicago)
| Departure | Arrival | Flight days | Flight | Airlines | Flight time | Airports | |
|---|---|---|---|---|---|---|---|
| 06:30 | 12:40 | mon, tue, thu | WN2077 | Southwest Airlines | 4h 10m | Norman Y. Mineta San Jose International Airport — Chicago Midway International Airport | Select dates |
| 07:00 | 13:10 | sat | WN2077 | Southwest Airlines | 4h 10m | Norman Y. Mineta San Jose International Airport — Chicago Midway International Airport | Select dates |
| 11:05 | 17:10 | tue, wed | WN3720 | Southwest Airlines | 4h 5m | Norman Y. Mineta San Jose International Airport — Chicago Midway International Airport | Select dates |
| 11:40 | 17:45 | mon, thu, fri | WN3720 | Southwest Airlines | 4h 5m | Norman Y. Mineta San Jose International Airport — Chicago Midway International Airport | Select dates |
| 11:55 | 17:55 | sun | WN1142 | Southwest Airlines | 4h 0m | Norman Y. Mineta San Jose International Airport — Chicago Midway International Airport | Select dates |
| 12:25 | 18:30 | mon, thu, fri, sun | WN2077 | Southwest Airlines | 4h 5m | Norman Y. Mineta San Jose International Airport — Chicago Midway International Airport | Select dates |
| 22:55 | 05:00 | mon, tue, wed, fri, sat, sun | WN4447 | Southwest Airlines | 4h 5m | Norman Y. Mineta San Jose International Airport — Chicago Midway International Airport | Select dates |
| 22:55 | 05:16 | fri | UA1692 | United Express | 4h 21m | Norman Y. Mineta San Jose International Airport — O'Hare International Airport | Select dates |
| 22:55 | 05:14 | mon, tue, wed, thu, sat, sun | UA1692 | United Express | 4h 19m | Norman Y. Mineta San Jose International Airport — O'Hare International Airport | Select dates |
| 22:55 | 06:14 | sun | UA1692 | United Express | 4h 19m | Norman Y. Mineta San Jose International Airport — O'Hare International Airport | Select dates |