Using the online timetable is an easy way to look at all the direct flights San Jose — Chicago
40 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 | 12:43 | mon, wed, thu, fri, sat, sun | UA374 | United Airlines | 4h 23m | Norman Y. Mineta San Jose International Airport — O'Hare International Airport | Select dates |
| 06:20 | 12:42 | sun | UA374 | United Airlines | 4h 22m | Norman Y. Mineta San Jose International Airport — O'Hare International Airport | Select dates |
| 06:35 | 12:58 | thu | UA374 | United Airlines | 4h 23m | Norman Y. Mineta San Jose International Airport — O'Hare International Airport | Select dates |
| 06:35 | 13:01 | mon, tue, wed, fri, sat, sun | UA374 | United Airlines | 4h 26m | Norman Y. Mineta San Jose International Airport — O'Hare International Airport | Select dates |
| 06:35 | 12:57 | mon, tue, wed, thu, fri | UA374 | United Airlines | 4h 22m | Norman Y. Mineta San Jose International Airport — O'Hare International Airport | Select dates |
| 06:35 | 12:45 | tue, wed | WN3869 | Southwest Airlines | 4h 10m | Norman Y. Mineta San Jose International Airport — Chicago Midway International Airport | Select dates |
| 06:40 | 12:50 | tue, wed | WN2463 | Southwest Airlines | 4h 10m | Norman Y. Mineta San Jose International Airport — Chicago Midway International Airport | Select dates |
| 06:50 | 12:55 | sat | WN1039 | Southwest Airlines | 4h 5m | Norman Y. Mineta San Jose International Airport — Chicago Midway International Airport | Select dates |
| 06:55 | 13:05 | sat | WN878 | Southwest Airlines | 4h 10m | Norman Y. Mineta San Jose International Airport — Chicago Midway International Airport | Select dates |
| 08:20 | 14:25 | mon, thu, fri | WN1039 | Southwest Airlines | 4h 5m | Norman Y. Mineta San Jose International Airport — Chicago Midway International Airport | Select dates |
| 08:35 | 14:45 | tue, wed | WN1039 | Southwest Airlines | 4h 10m | 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 |
| 13:30 | 19:35 | sun | WN1039 | Southwest Airlines | 4h 5m | 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 |
| 14:25 | 20:30 | wed | WN4508 | Southwest Airlines | 4h 5m | Norman Y. Mineta San Jose International Airport — Chicago Midway International Airport | Select dates |
| 18:25 | 00:30 | tue, fri, sat | WN4508 | Southwest Airlines | 4h 5m | Norman Y. Mineta San Jose International Airport — Chicago Midway International Airport | Select dates |