Using the online timetable is an easy way to look at all the direct flights San Jose — Chicago
27 flights in a week
Departure and arrival times are local (San Jose and Chicago)
| Departure | Arrival | Flight days | Flight | Airlines | Flight time | Airports | |
|---|---|---|---|---|---|---|---|
| 06:20 | 12:42 | daily | UA374 | United Airlines | 4h 22m | Norman Y. Mineta San Jose International Airport — O'Hare International Airport | Select dates |
| 06:35 | 12:45 | tue, wed | WN2546 | Southwest Airlines | 4h 10m | Norman Y. Mineta San Jose International Airport — Chicago Midway International Airport | Select dates |
| 07:00 | 13:05 | sun | WN3803 | Southwest Airlines | 4h 5m | Norman Y. Mineta San Jose International Airport — Chicago Midway International Airport | Select dates |
| 07:25 | 13:30 | sat | WN2409 | Southwest Airlines | 4h 5m | Norman Y. Mineta San Jose International Airport — Chicago Midway International Airport | Select dates |
| 08:00 | 14:10 | mon, thu, fri | WN2409 | Southwest Airlines | 4h 10m | Norman Y. Mineta San Jose International Airport — Chicago Midway International Airport | Select dates |
| 08:00 | 14:05 | mon, thu, fri | WN3803 | Southwest Airlines | 4h 5m | Norman Y. Mineta San Jose International Airport — Chicago Midway International Airport | Select dates |
| 08:35 | 14:45 | sat | WN3803 | Southwest Airlines | 4h 10m | Norman Y. Mineta San Jose International Airport — Chicago Midway International Airport | Select dates |
| 08:40 | 14:45 | sun | WN2409 | Southwest Airlines | 4h 5m | Norman Y. Mineta San Jose International Airport — Chicago Midway International Airport | Select dates |
| 09:20 | 15:30 | tue, wed | WN2409 | Southwest Airlines | 4h 10m | Norman Y. Mineta San Jose International Airport — Chicago Midway International Airport | Select dates |
| 10:10 | 16:15 | sat | WN3869 | Southwest Airlines | 4h 5m | Norman Y. Mineta San Jose International Airport — Chicago Midway International Airport | Select dates |
| 10:40 | 16:50 | tue, wed | WN3803 | Southwest Airlines | 4h 10m | Norman Y. Mineta San Jose International Airport — Chicago Midway International Airport | Select dates |
| 13:35 | 19:40 | mon, thu, fri | WN3869 | Southwest Airlines | 4h 5m | Norman Y. Mineta San Jose International Airport — Chicago Midway International Airport | Select dates |