Flight Routes from San Diego to Chicago Midway

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

Trip type
Cheapest roundtrip flight
from€335
Fastest outbound flight
Fastest inbound flight
non-stop flights
44x / week
Flight distance
2,779 km
Time difference

Flight schedule from San Diego (SAN) to Chicago Midway (MDW)

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

offers
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Matching outbound flightsSAN–MDW · 13 of 13
fromto
dep.arr.
durationstopovers
  1. October 18 – 24, 2026
  2. October 25 – 31, 2026
  3. November 1 – 7, 2026
    1. SANMDW
      nonstop
      1. Southwest Airlines
    2. SANMDW
      nonstop
      1. Southwest Airlines
    3. SANMDW
      nonstop
      1. Southwest Airlines
    4. SANMDW
      nonstop
      1. Southwest Airlines
    5. SANMDW
      nonstop
      1. Southwest Airlines
    6. SANMDW
      nonstop
      1. Southwest Airlines
    7. SANMDW
      nonstop
      1. Southwest Airlines
    8. SANMDW
      nonstop
      1. Southwest Airlines
    9. SANMDW
      nonstop
      1. Southwest Airlines
    10. SANMDW
      nonstop
      1. Southwest Airlines
    11. SANMDW
      nonstop
      1. Southwest Airlines
    12. SANMDW
      nonstop
      1. Southwest Airlines
    13. SANMDW
      nonstop
      1. Southwest Airlines

      Important flight information

      Discover more flights around San Diego and Chicago Midway

      Departure airport Airport San Diego - Lindberg Field International, CA (SAN)
      Arrival airport Airport Chicago Midway International Airport, IL (MDW)
      Destination country Flights to United States
      Departure airport - Destination country San Diego - Lindberg Field International, CA - United States
      Departure airport - City-Code San Diego - Lindberg Field International, CA - Chicago
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