Use the Orange Line train for a quick, cost-effective trip to MDW, taking less than 30 minutes from the city center.
Most accurate provider | FlightHub 3 stars |
---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $253 (Southwest) |
One-way from | $117 (Southwest) |
Popular in | November |
Cheapest in | May |
Average price | $352 |
Good round-trip deal | $464 or less |
Good one-way deal | $279 or less |
Fly from
Fly to
Route
Depart
Return
Price
ChicagoOakland
MDW - OAK
MDWOAK
Chicago Midway
mié. 11/5
12:05 pm-6:35 pm
1 stop8h 30m
Oakland
mié. 11/12
12:45 pm-10:55 pm
1 stop8h 10m
ChicagoOakland
MDW - OAK
MDWOAK
Chicago Midway
mié. 11/12
10:47 am-12:03 am
2 stops15h 16m
Oakland
mar. 11/18
5:55 am-6:08 pm
2 stops10h 13m
ChicagoOakland
MDW - OAK
MDWOAK
Chicago Midway
sáb. 11/1
1:45 pm-7:30 pm
1 stop7h 45m
Oakland
mar. 11/4
7:55 am-4:10 pm
1 stop6h 15m
ChicagoOakland
MDW - OAK
MDWOAK
Chicago Midway
sáb. 11/15
8:20 am-2:25 pm
1 stop8h 05m
Oakland
mar. 11/18
7:00 am-5:15 pm
2 stops8h 15m
ChicagoOakland
MDW - OAK
MDWOAK
Chicago Midway
jue. 11/13
8:25 am-2:15 pm
1 stop7h 50m
Oakland
lun. 11/17
7:50 am-4:55 pm
1 stop7h 05m
ChicagoOakland
MDW - OAK
MDWOAK
Chicago Midway
mié. 10/22
3:25 pm-7:50 pm
1 stop6h 25m
Oakland
dom. 10/26
7:20 pm-5:00 am
1 stop7h 40m
ChicagoOakland
MDW - OAK
MDWOAK
Chicago Midway
sáb. 12/6
2:05 pm-4:45 pm
Nonstop4h 40m
Oakland
lun. 12/8
9:10 am-4:55 pm
1 stop5h 45m
ChicagoOakland
MDW - OAK
MDWOAK
Chicago Midway
vie. 11/7
6:05 am-11:15 am
1 stop7h 10m
Oakland
lun. 11/10
5:25 am-11:30 am
Nonstop4h 05m
ChicagoOakland
MDW - OAK
MDWOAK
Chicago Midway
sáb. 12/6
2:05 pm-4:45 pm
Nonstop4h 40m
Oakland
sáb. 12/13
3:00 pm-10:45 pm
1 stop5h 45m
ChicagoOakland
MDW - OAK
MDWOAK
Chicago Midway
mié. 10/22
4:15 pm-6:50 pm
Nonstop4h 35m
Provider | Price Accuracy | Trust Score* |
---|---|---|
Price Accuracy2 stars | Trust Score*3 stars | |
Price Accuracy3 stars | Trust Score*3 stars | |
Price Accuracy3 stars | Trust Score*3 stars |
Currently, April is the cheapest month in which you can book a flight from Chicago Midway Airport to Oakland, California (average of $183). Flying from Chicago Midway Airport to Oakland, California in November is currently the most expensive (average of $259). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
It’s typically best to fly out from Chicago Midway Airport to Oakland, California at noon. Doing so could potentially save you 40% on the flight price compared to flying in the morning, which is usually more expensive.
Comfort
Entertainment
Overall
Food
Boarding
Crew
Reviews
Walter,Aug 2025
OAK - SAN
Comfort
Entertainment
Overall
Food
Boarding
Crew
Reviews
Walter,Aug 2025
OAK - SAN
Airline | Cheapest | Average | Flexibility | On-time |
---|---|---|---|---|
Cheapest$247 | Average$366 | FlexibilityNo cancel fee | On-time63% |