Using the online timetable is an easy way to look at all the direct flights Oakland — Chicago
24 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 (Heart Livery) | 4h 10m | Metropolitan Oakland International Airport — Chicago Midway International Airport | Select dates |
| 05:15 | 11:20 | thu, fri | WN3123 | Southwest Airlines (Heart Livery) | 4h 5m | Metropolitan Oakland International Airport — Chicago Midway International Airport | Select dates |
| 05:50 | 12:00 | tue, wed | WN189 | Southwest Airlines (Heart Livery) | 4h 10m | Metropolitan Oakland International Airport — Chicago Midway International Airport | Select dates |
| 05:55 | 12:05 | mon, thu, fri | WN585 | Southwest Airlines (Heart Livery) | 4h 10m | Metropolitan Oakland International Airport — Chicago Midway International Airport | Select dates |
| 06:05 | 12:15 | sat, sun | WN189 | Southwest Airlines (Heart Livery) | 4h 10m | Metropolitan Oakland International Airport — Chicago Midway International Airport | Select dates |
| 06:15 | 12:25 | sat | WN585 | Southwest Airlines (Heart Livery) | 4h 10m | Metropolitan Oakland International Airport — Chicago Midway International Airport | Select dates |
| 06:20 | 12:30 | sun | WN585 | Southwest Airlines (Heart Livery) | 4h 10m | Metropolitan Oakland International Airport — Chicago Midway International Airport | Select dates |
| 07:00 | 12:56 | fri | K9134 | Kalitta Charters | 3h 56m | Metropolitan Oakland International Airport — Chicago Midway International Airport | Select dates |
| 07:40 | 13:45 | fri | WN585 | Southwest Airlines (Heart Livery) | 4h 5m | Metropolitan Oakland International Airport — Chicago Midway International Airport | Select dates |
| 12:05 | 18:10 | tue, wed | WN585 | Southwest Airlines (Heart Livery) | 4h 5m | Metropolitan Oakland International Airport — Chicago Midway International Airport | Select dates |
| 13:10 | 19:10 | sun | WN2853 | Southwest Airlines (Heart Livery) | 4h 0m | Metropolitan Oakland International Airport — Chicago Midway International Airport | Select dates |
| 15:10 | 21:10 | sun | WN3105 | Southwest Airlines (Heart Livery) | 4h 0m | Metropolitan Oakland International Airport — Chicago Midway International Airport | Select dates |
| 19:25 | 00:58 | mon, tue, wed, fri | 5X947 | UPS | 3h 33m | Metropolitan Oakland International Airport — Chicago Rockford International Airport | Select dates |