Flight Routes from Portland Oregon to Chicago

Compare cheap outbound and return flights from Portland-Oregon (PDX) to Chicago (CHI) and find the best offer from numerous airlines and travel agencies.

Trip type
Fastest outbound flight
Fastest inbound flight
non-stop flights
48x / week
Flight distance
2,820 km
Time difference
Airports in Chicago
  1. O'Hare International Airport, IL
  2. Midway International Airport, IL
  3. Rockford, IL

Flight schedule from Portland-Oregon (PDX) to Chicago (CHI)

Select a travel date in the flight schedule for the route from Portland-Oregon (PDX) to Chicago (CHI) and compare affordable flight deals.

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

      Important flight information

      Discover more flights around Portland-Oregon and Chicago

      Departure airport Airport Portland International Airport, Oregon (PDX)
      Arrival airport Airport Chicago-IL, all airports (CHI)
      Destination country Flights to United States
      Departure airport - Destination country Portland International Airport, Oregon - United States
      Alternative routes to United States
      Alternative flights to Chicago
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