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
Cheapest roundtrip flight
from€1,023
Fastest outbound flight
Fastest inbound flight
non-stop flights
49x / week
Flight distance
2,964 km
Time difference

Cheap flight offers from Oakland to Chicago Midway

sorted by price and recency
  1. –
    Volaris
    –
    OAK–MDW
    1 stopover
    Volaris
    –
    MDW–OAK
    1 stopover
    €1,023

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
Active filtersnone
Matching outbound flightsOAK–MDW · 5 of 5
fromto
dep.arr.
durationstopovers
  1. November 8 – 14, 2026
  2. November 15 – 21, 2026
  3. November 22 – 28, 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

      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
      Flight destinations with a similar price
      Flight destinations with a similar price