Flights Chicago to Oakland MDW to OAK

Flights from Chicago (MDW) to Oakland (OAK): 2 airlines operate 32 flight numbers on this route, about 7 flights a week, distance 2961 km / 1840 miles. No departures are scheduled in the next 30 days; the latest flight was WN2990 on Fri, Nov 13, 2026.

Airlines and flight numbers count operating flights from a year ago to a year ahead; code-share numbers are not counted. On time means landed less than 15 minutes late.

MDW Chicago Chicago Midway International Airport OAK Oakland Oakland International Airport
Route map MDW to OAK Great-circle route from Chicago Midway International Airport, United States to Oakland International Airport, United States, 2961 km. Map data: Natural Earth. UNITED STATES MDW OAK Map data: Natural Earth

Chicago to Oakland Flights

The 30 most recent of 32 flight numbers from MDW to OAK, with the date each last flew. Local times: MDW CST, OAK PST.

Flight Airline Last seen Departure Arrival
WN2990 Southwest Airlines Nov 13, 2026 21:55 00:40
WN3174 Southwest Airlines Nov 13, 2026 10:05 12:45
WN1364 Southwest Airlines Nov 11, 2026 20:45 23:35
WN2865 Southwest Airlines Oct 31, 2026 10:35 13:15
WN4293 Southwest Airlines Oct 30, 2026 21:30 00:15
WN4280 Southwest Airlines Oct 30, 2026 10:05 12:45
WN818 Southwest Airlines Oct 28, 2026 20:35 23:20
WN2015 Southwest Airlines Oct 25, 2026 21:25 00:10
WN3587 Southwest Airlines Oct 24, 2026 19:30 22:10
JL12 Japan Airlines Oct 13, 2026 17:15 19:12
WN1413 Southwest Airlines Sep 30, 2026 20:35 23:10
WN2779 Southwest Airlines Sep 30, 2026 10:15 12:40
WN3461 Southwest Airlines Sep 27, 2026 20:25 23:00
WN4042 Southwest Airlines Aug 3, 2026 21:40 00:15
WN3366 Southwest Airlines Aug 3, 2026 10:10 12:40
WN2221 Southwest Airlines Aug 1, 2026 13:20 15:50
WN2710 Southwest Airlines Jul 29, 2026 21:00 23:35
WN1743 Southwest Airlines Jun 3, 2026 20:50 23:25
WN192 Southwest Airlines Jun 3, 2026 10:00 12:35
WN1748 Southwest Airlines Jun 1, 2026 21:50 00:25
WN1394 Southwest Airlines Apr 6, 2026 21:30 00:10
WN2484 Southwest Airlines Apr 6, 2026 10:05 12:50
WN1371 Southwest Airlines Mar 4, 2026 11:10 14:05
WN2977 Southwest Airlines Mar 2, 2026 08:10 11:05
WN1369 Southwest Airlines Mar 1, 2026 07:55 10:50
WN470 Southwest Airlines Feb 28, 2026 20:55 23:50
WN3055 Southwest Airlines Feb 7, 2026 19:40 22:35
WN1700 Southwest Airlines Jan 5, 2026 07:45 10:25
WN2376 Southwest Airlines Jan 4, 2026 07:50 10:35
WN3213 Southwest Airlines Jan 3, 2026 22:50 01:30

Upcoming flights

Local times at the departure airport.

No upcoming flights for this route.

Recent flights

Local times at the departure airport.
Flight From To Date Scheduled Time Departure Status Details
WN2990 Chicago MDW Oakland OAK Nov 13 21:55 00:14 Delayed Track >
WN3174 Chicago MDW Oakland OAK Nov 13 10:05 10:17 Landed Track >
WN2990 Chicago MDW Oakland OAK Nov 12 21:55 23:19 Landed Late Track >
WN3174 Chicago MDW Oakland OAK Nov 12 10:05 10:29 Landed Track >
WN1364 Chicago MDW Oakland OAK Nov 11 20:45 21:13 Landed Track >
WN3174 Chicago MDW Oakland OAK Nov 11 10:00 11:23 Landed Late Track >
WN1364 Chicago MDW Oakland OAK Nov 10 20:45 20:55 Landed Track >
WN3174 Chicago MDW Oakland OAK Nov 10 10:00 10:30 Landed Track >
WN2990 Chicago MDW Oakland OAK Nov 09 21:55 22:32 Landed Track >
WN3174 Chicago MDW Oakland OAK Nov 09 10:05 10:33 Landed Track >
WN2990 Chicago MDW Oakland OAK Nov 08 21:55 22:40 Landed Track >
WN3174 Chicago MDW Oakland OAK Nov 08 10:05 10:34 Landed Track >
WN3174 Chicago MDW Oakland OAK Nov 07 12:55 13:44 Landed Track >
WN2990 Chicago MDW Oakland OAK Nov 06 21:55 22:23 Landed Track >
WN3174 Chicago MDW Oakland OAK Nov 06 10:05 10:23 Landed Track >

Airlines flying MDW to OAK

MDW to OAK FAQ

How long is the flight from Chicago to Oakland?
About 3 h 55 min: that is the median flight time of the last 14 flights that landed; the timetable allows 4 h 45 min.
Which airlines fly from Chicago to Oakland?
Southwest Airlines and Japan Airlines have flights from Chicago (MDW) to Oakland (OAK) between a year ago and a year ahead. An airline listed may not fly the route every day.
How many flights a week go from Chicago to Oakland?
About 7 flights a week, counted over the two weeks before and after today. Only operating flights are counted, not code-share numbers.
Are flights from Chicago to Oakland on time?
12 of the last 14 flights that landed arrived less than 15 minutes after their scheduled time.
How far is Chicago from Oakland?
2961 km (1840 miles) in a straight line between Chicago Midway International Airport and Oakland International Airport.

Oakland (OAK) to Chicago (MDW) flights >