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
Cheapest roundtrip flight
from€358
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

Cheap flight offers from Portland-Oregon to Chicago

sorted by price and recency
filters
  1. –
    Alaska Airlines
    –
    PDX–CHI
    non-stop flight
    Frontier Airlines
    –
    CHI–PDX
    1 stopover
    €358
  2. –
    American Airlines
    –
    PDX–CHI
    non-stop flight
    American Airlines
    –
    CHI–PDX
    non-stop flight
    €516
  3. –
    Alaska Airlines
    –
    PDX–CHI
    non-stop flight
    Alaska Airlines
    –
    CHI–PDX
    non-stop flight
    €407
  4. –
    Southwest Airlines
    –
    PDX–CHI
    non-stop flight
    Southwest Airlines
    –
    CHI–PDX
    non-stop flight
    €401
  5. –
    Alaska Airlines
    –
    PDX–CHI
    1 stopover
    Volaris
    –
    CHI–PDX
    1 stopover
    €893
  6. –
    Alaska Airlines
    –
    PDX–CHI
    non-stop flight
    American Airlines
    –
    CHI–PDX
    non-stop flight
    €605

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 · 17 of 17
fromto
dep.arr.
durationstopovers
  1. November 1 – 7, 2026
  2. November 8 – 14, 2026
  3. November 15 – 21, 2026
    1. PDXMDW
      nonstop
      1. Southwest Airlines
    2. PDXMDW
      nonstop
      1. Southwest Airlines
    3. PDXORD
      nonstop
      1. American 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. American Airlines
    12. PDXORD
      nonstop
      1. United Airlines
    13. PDXORD
      nonstop
      1. United Airlines
    14. PDXORD
      nonstop
      1. Alaska Airlines
    15. PDXORD
      nonstop
      1. American 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
      Flight destinations with a similar price
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