Direct flights from Chicago to Portland (MDW → PDX)

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

Available flights

Southwest AirlinesNon-stop
from$329
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Frequently asked questions

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

Cheapest fares Chicago → Portland

Chicago MDW
Portland PDX
May from $231 June from $231 July from $192 August — September — October —

Related guides for this route

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

Cheap flights from Chicago to Portland Cheapest month to fly to Portland 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 Chicago

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

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

Or try a nearby airport to Portland

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

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

Other flights from Portland (PDX)

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