Flight Routes from Chicago Midway to Oakland

Compare cheap outbound and return flights from Chicago Midway (MDW) to Oakland (OAK) and find the best offer from numerous airlines and travel agencies.

Trip type
Cheapest roundtrip flight
from€344
Fastest outbound flight
Fastest inbound flight
non-stop flights
63x / week
Flight distance
2,964 km
Time difference

Flight schedule from Chicago Midway (MDW) to Oakland (OAK)

Select a travel date in the flight schedule for the route from Chicago Midway (MDW) to Oakland (OAK) and compare affordable flight deals.

offers
Active filtersnone
Matching outbound flightsMDW–OAK · 8 of 8
fromto
dep.arr.
durationstopovers
  1. October 4 – 10, 2026
  2. October 11 – 17, 2026
  3. October 18 – 24, 2026
    1. MDWOAK
      nonstop
      1. Southwest Airlines
    2. MDWOAK
      nonstop
      1. Southwest Airlines
    3. MDWOAK
      nonstop
      1. Southwest Airlines
    4. MDWOAK
      nonstop
      1. Southwest Airlines
    5. MDWOAK
      nonstop
      1. Southwest Airlines
    6. MDWOAK
      nonstop
      1. Southwest Airlines
    7. MDWOAK
      nonstop
      1. Southwest Airlines
    8. MDWOAK
      nonstop
      1. Southwest Airlines

      Important flight information

      Discover more flights around Chicago Midway and Oakland

      Departure airport Airport Chicago Midway International Airport, IL (MDW)
      Arrival airport Airport Oakland International Airport, CA (OAK)
      Destination country Flights to United States
      City-Code - Arrival airport Chicago - Oakland International Airport, CA
      Departure airport - Destination country Chicago Midway International Airport, IL - United States
      Alternative routes to United States
      Alternative flights to Oakland
      Flight destinations with a similar price
      Flight destinations with a similar price