Flight Routes from Oakland to Chicago Midway

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

Trip type
Fastest outbound flight
Fastest inbound flight
non-stop flights
49x / week
Flight distance
2,964 km
Time difference

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

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

offers
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Matching outbound flightsOAK–MDW · 12 of 12
fromto
dep.arr.
durationstopovers
  1. September 20 – 26, 2026
  2. Sep 27 – Oct 3, 2026
  3. October 4 – 10, 2026
    1. OAKMDW
      nonstop
      1. Southwest Airlines
    2. OAKMDW
      nonstop
      1. Southwest Airlines
    3. OAKMDW
      nonstop
      1. Southwest Airlines
    4. OAKMDW
      nonstop
      1. Southwest Airlines
    5. OAKMDW
      nonstop
      1. Southwest Airlines
    6. OAKMDW
      nonstop
      1. Southwest Airlines
    7. OAKMDW
      nonstop
      1. Southwest Airlines
    8. OAKMDW
      nonstop
      1. Southwest Airlines
    9. OAKMDW
      nonstop
      1. Southwest Airlines
    10. OAKMDW
      nonstop
      1. Southwest Airlines
    11. OAKMDW
      nonstop
      1. Southwest Airlines
    12. OAKMDW
      nonstop
      1. Southwest Airlines

      Important flight information

      Discover more flights around Oakland and Chicago Midway

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