Direct flights from Portland to Chicago (PDX → MDW)

Distance 2,811 km (1,747 mi)
Est. duration 3h 18m
PDX
Portland
Portland International, USA
MDW
Chicago
Chicago Midway International, USA
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Live fares · PDX → MDW

Available flights

Southwest AirlinesNon-stop
from$145
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Frequently asked questions

How far is the flight from Portland to Chicago? The flight distance from PDX to MDW is approximately 2,811 km (1,747 miles).
How long is the flight from PDX to MDW? The estimated flight time from Portland to Chicago is approximately 3h 18m.
What airlines fly from PDX to MDW? Airlines operating direct flights from Portland to Chicago include: WN.

Cheapest fares Portland → Chicago

Portland PDX
Chicago MDW
May — June — July — August — September — October —

Related guides for this route

Sibling pages from across Flightmaps — fares, visa rules, country aggregations, and per-airline routes for Portland → Chicago.

Cheap flights from Portland to Chicago Cheapest month to fly to Chicago Flights from USA Flights to USA Visa-free with USA passport All airports in USA WN routes & destinations All routes by this carrier

Try a nearby airport to Portland

Flights to Chicago (MDW) from other airports within 350 km of Portland. Often unlocks cheaper fares or better times.

EUG → MDW 170 km from PDX Eugene → Chicago USA · 17 destinations RDM → MDW 187 km from PDX Redmond → Chicago USA · 10 destinations SEA → MDW 207 km from PDX Seattle → Chicago USA · 139 destinations PAE → MDW 259 km from PDX Everett → Chicago USA · 9 destinations PSC → MDW 279 km from PDX Pasco → Chicago USA · 12 destinations

Or try a nearby airport to Chicago

Flights from Portland (PDX) to other airports within 350 km of Chicago.

PDX → ORD 25 km from MDW Portland → Chicago USA · 282 destinations PDX → SBN 119 km from MDW Portland → South Bend USA · 22 destinations PDX → RFD 121 km from MDW Portland → Rockford USA · 8 destinations PDX → MKE 130 km from MDW Portland → Milwaukee USA · 34 destinations PDX → BMI 175 km from MDW Portland → Bloomington USA · 6 destinations

Other flights from Portland (PDX)

Albuquerque (ABQ) Amsterdam (AMS) Anchorage (ANC) Appleton (ATW) Atlanta (ATL) Austin (AUS) Baltimore (BWI) Bellingham (BLI) All 90 destinations →

Other flights from Chicago (MDW)

Aguascalientes (AGU) Albany (ALB) Albuquerque (ABQ) Asheville (AVL) Atlanta (ATL) Austin (AUS) Baltimore (BWI) Birmingham (BHM) All 97 destinations →