Flight Routes from Portland Oregon to Chicago Midway

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

Trip type
Cheapest roundtrip flight
from€401
Fastest outbound flight
Fastest inbound flight
non-stop flights
16x / week
Flight distance
2,814 km
Time difference

Cheap flight offers from Portland-Oregon to Chicago Midway

sorted by price and recency
filters
  1. –
    Alaska Airlines
    –
    PDX–MDW
    2 stopovers
    Aeroméxico
    –
    MDW–PDX
    3 stopovers
    €1,499
  2. –
    Southwest Airlines
    –
    PDX–MDW
    non-stop flight
    Southwest Airlines
    –
    MDW–PDX
    non-stop flight
    €401

Flight schedule from Portland-Oregon (PDX) to Chicago Midway (MDW)

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

offers
Active filtersnone
Matching outbound flightsPDX–MDW · 5 of 5
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. PDXMDW
      nonstop
      1. Southwest Airlines
    4. PDXMDW
      nonstop
      1. Southwest Airlines
    5. PDXMDW
      nonstop
      1. Southwest Airlines

      Important flight information

      Discover more flights around Portland-Oregon and Chicago Midway

      Departure airport Airport Portland International Airport, Oregon (PDX)
      Arrival airport Airport Chicago Midway International Airport, IL (MDW)
      Destination country Flights to United States
      Departure airport - Destination country Portland International Airport, Oregon - United States
      Departure airport - City-Code Portland International Airport, Oregon - Chicago