Direct flights from Chicago to Portland (MDW → PWM)

Distance 1,436 km (892 mi)
Est. duration 1h 41m
MDW
Chicago
Chicago Midway International, USA
PWM
Portland
Portland International Jetport, USA
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Live fares · MDW → PWM

Available flights

Southwest AirlinesNon-stop
from$267
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Frequently asked questions

How far is the flight from Chicago to Portland? The flight distance from MDW to PWM is approximately 1,436 km (892 miles).
How long is the flight from MDW to PWM? The estimated flight time from Chicago to Portland is approximately 1h 41m.
What airlines fly from MDW to PWM? Airlines operating direct flights from Chicago to Portland include: WN.

Cheapest fares Chicago → Portland

Chicago MDW
Portland PWM
May — June — July — August — September from $187 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 (PWM) from other airports within 350 km of Chicago. Often unlocks cheaper fares or better times.

ORD → PWM 25 km from MDW Chicago → Portland USA · 282 destinations SBN → PWM 119 km from MDW South Bend → Portland USA · 22 destinations RFD → PWM 121 km from MDW Rockford → Portland USA · 8 destinations MKE → PWM 130 km from MDW Milwaukee → Portland USA · 34 destinations BMI → PWM 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 → PSM 76 km from PWM Chicago → Portsmouth USA · 6 destinations MDW → MHT 121 km from PWM Chicago → Manchester USA · 15 destinations MDW → BOS 154 km from PWM Chicago → Boston USA · 153 destinations MDW → BGR 176 km from PWM Chicago → Bangor USA · 17 destinations MDW → ORH 199 km from PWM Chicago → Worcester USA · 5 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 (PWM)

Akron (CAK) Atlanta (ATL) Baltimore (BWI) Charleston (CHS) Charlotte (CLT) Chicago (ORD) Cincinnati (CVG) Columbus (CMH) All 31 destinations →