Using the online timetable is an easy way to look at all the direct flights Oakland — Chicago
20 flights in a week
Departure and arrival times are local (Oakland and Chicago)
| Departure | Arrival | Flight days | Flight | Airlines | Flight time | Airports | |
|---|---|---|---|---|---|---|---|
| 05:05 | 11:15 | mon, thu, fri | WN189 | Southwest Airlines | 4h 10m | Metropolitan Oakland International Airport — Chicago Midway International Airport | Select dates |
| 05:50 | 12:00 | wed | WN189 | Southwest Airlines | 4h 10m | Metropolitan Oakland International Airport — Chicago Midway International Airport | Select dates |
| 05:55 | 12:05 | sun | WN189 | Southwest Airlines | 4h 10m | Metropolitan Oakland International Airport — Chicago Midway International Airport | Select dates |
| 06:05 | 12:15 | sat | WN189 | Southwest Airlines | 4h 10m | Metropolitan Oakland International Airport — Chicago Midway International Airport | Select dates |
| 06:10 | 12:15 | sun | WN1665 | Southwest Airlines | 4h 5m | Metropolitan Oakland International Airport — Chicago Midway International Airport | Select dates |
| 06:25 | 11:51 | tue, wed, thu | 5X2953 | UPS | 3h 26m | Metropolitan Oakland International Airport — Chicago Rockford International Airport | Select dates |
| 06:25 | 11:55 | tue, thu | 5X2953 | UPS | 3h 30m | Metropolitan Oakland International Airport — Chicago Rockford International Airport | Select dates |
| 06:25 | 12:00 | tue, wed, thu | 5X2953 | UPS | 3h 35m | Metropolitan Oakland International Airport — Chicago Rockford International Airport | Select dates |
| 06:25 | 12:37 | wed | 5X2953 | UPS | 4h 12m | Metropolitan Oakland International Airport — Chicago Rockford International Airport | Select dates |
| 06:35 | 12:40 | sat | WN346 | Southwest Airlines | 4h 5m | Metropolitan Oakland International Airport — Chicago Midway International Airport | Select dates |
| 11:05 | 17:10 | tue, wed | WN1665 | Southwest Airlines | 4h 5m | Metropolitan Oakland International Airport — Chicago Midway International Airport | Select dates |
| 11:25 | 17:30 | mon | WN1665 | Southwest Airlines | 4h 5m | Metropolitan Oakland International Airport — Chicago Midway International Airport | Select dates |