Direct flights from Portland to Chicago (PWM → MDW)

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

Frequently asked questions

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

Cheapest fares Portland → Chicago

Portland PWM
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.

PSM → MDW 76 km from PWM Portsmouth → Chicago USA · 6 destinations MHT → MDW 121 km from PWM Manchester → Chicago USA · 15 destinations BOS → MDW 154 km from PWM Boston → Chicago USA · 153 destinations BGR → MDW 176 km from PWM Bangor → Chicago USA · 17 destinations ORH → MDW 199 km from PWM Worcester → Chicago USA · 5 destinations

Or try a nearby airport to Chicago

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

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

Other flights from Chicago (MDW)

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