Flight Routes from Madison to Chicago

Compare cheap outbound and return flights from Madison (MSN) to Chicago (CHI) and find the best offer from numerous airlines and travel agencies.

Trip type
Fastest flight
non-stop flights
94x / week
Flight distance
198 km
Time difference
none
Airports in Chicago
  1. O'Hare International Airport, IL
  2. Midway International Airport, IL
  3. Rockford, IL

Flight schedule from Madison (MSN) to Chicago (CHI)

Select a travel date in the flight schedule for the route from Madison (MSN) to Chicago (CHI) and compare affordable flight deals.

offers
Active filtersnone
Matching outbound flightsMSN–CHI · 33 of 33
fromto
dep.arr.
durationstopovers
  1. September 13 – 19, 2026
  2. September 20 – 26, 2026
  3. Sep 27 – Oct 3, 2026
    1. MSNORD
      nonstop
      1. United Airlines
    2. MSNORD
      nonstop
      1. United Airlines
    3. MSNORD
      nonstop
      1. American Airlines
    4. MSNORD
      nonstop
      1. American Airlines
    5. MSNORD
      nonstop
      1. United Airlines
    6. MSNORD
      nonstop
      1. United Airlines
    7. MSNORD
      nonstop
      1. United Airlines
    8. MSNORD
      nonstop
      1. American Airlines
    9. MSNORD
      nonstop
      1. United Airlines
    10. MSNORD
      nonstop
      1. United Airlines
    11. MSNORD
      nonstop
      1. American Airlines
    12. MSNORD
      nonstop
      1. United Airlines
    13. MSNORD
      nonstop
      1. United Airlines
    14. MSNORD
      nonstop
      1. United Airlines
    15. MSNORD
      nonstop
      1. United Airlines

      Important flight information

      Discover more flights around Madison and Chicago

      Departure airport Airport Madison, WI (MSN)
      Arrival airport Airport Chicago-IL, all airports (CHI)
      Destination country Flights to United States
      Departure airport - Destination country Madison, WI - United States
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