Flight Routes from San Jose to Chicago Midway

Compare cheap outbound and return flights from San Jose (SJC) 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
45x / week
Flight distance
2,954 km
Time difference

Flight schedule from San Jose (SJC) to Chicago Midway (MDW)

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

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

      Important flight information

      Discover more flights around San Jose and Chicago Midway

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