Flight Routes from Chicago Midway to San Jose

Compare cheap outbound and return flights from Chicago Midway (MDW) to San Jose (SJC) 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 Chicago Midway (MDW) to San Jose (SJC)

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

offers
Active filtersnone
Matching outbound flightsMDW–SJC · 15 of 15
fromto
dep.arr.
durationstopovers
  1. September 20 – 26, 2026
  2. Sep 27 – Oct 3, 2026
  3. October 4 – 10, 2026
    1. MDWSJC
      nonstop
      1. Southwest Airlines
    2. MDWSJC
      nonstop
      1. Southwest Airlines
    3. MDWSJC
      nonstop
      1. Southwest Airlines
    4. MDWSJC
      nonstop
      1. Southwest Airlines
    5. MDWSJC
      nonstop
      1. Southwest Airlines
    6. MDWSJC
      nonstop
      1. Southwest Airlines
    7. MDWSJC
      nonstop
      1. Southwest Airlines
    8. MDWSJC
      nonstop
      1. Southwest Airlines
    9. MDWSJC
      nonstop
      1. Southwest Airlines
    10. MDWSJC
      nonstop
      1. Southwest Airlines
    11. MDWSJC
      nonstop
      1. Southwest Airlines
    12. MDWSJC
      nonstop
      1. Southwest Airlines
    13. MDWSJC
      nonstop
      1. Southwest Airlines
    14. MDWSJC
      nonstop
      1. Southwest Airlines
    15. MDWSJC
      nonstop
      1. Southwest Airlines

      Important flight information

      Discover more flights around Chicago Midway and San Jose

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