Cheap Flights from Chicago to Portland
Cheap Flights from Chicago to Portland
Looking for cheap flights from Chicago to Portland? PointsYeah scans award availability across major airline and bank transfer programs in one place, so travelers can compare the lowest points and cash routes faster. Instead of searching each airline separately, users can see pricing from programs like Chase, Amex, Capital One, Citi, and Bilt side by side.
Award prices from Chicago to Portland vary by season, cabin, and date, but available award flights can start around 7,500 points one way, with premium cabins available at higher mileage levels. The live search above allows filtering by cabin, airline, stops, or maximum points to find the best award flights from Chicago to Portland for specific travel dates.
2026-11-06
ORD - PWM
Economy | Non stop | 7 left
From 7,500 Pts + $25.6
2026-11-07
ORD - PWM
Economy | Non stop | 9+ left
From 7,500 Pts + $25.6
2026-11-09
ORD - PWM
Economy | Non stop | 9+ left
From 7,500 Pts + $25.6
2026-11-10
ORD - PWM
Economy | Non stop | 9+ left
From 7,500 Pts + $25.6
2026-11-11
ORD - PWM
Economy | Non stop | 6 left
From 7,500 Pts + $25.6
2026-11-14
ORD - PWM
Economy | Non stop | 9+ left
From 7,500 Pts + $25.6
Chicago to Portland flight facts
Distance
902 mi
1,452 km in a straight line
Estimated flight time
about 2h 15m
In the air, for the straight-line distance
Time difference
+1h
Portland is 1 hour ahead of Chicago.
Airports in Chicago
DPA · Dupage
MDW · Chicago Midway Intl
ORD · Chicago O'Hare Intl
Airports in Portland
PWM · Portland Intl Jetport
Nearby airport alternatives
Flights Chicago - Manchester NH · Manchester NH is 75 mi from Portland
Flights Chicago - Boston · Boston is 95 mi from Portland
Flights Chicago - Bangor · Bangor is 109 mi from Portland
Flights Chicago - Bar Harbor · Bar Harbor is 112 mi from Portland
Flights Chicago - Worcester · Worcester is 124 mi from Portland
Flights Chicago - Providence · Providence is 144 mi from Portland
Premium cabin flights from Chicago to Portland
Premium cabin
2026-11-15
ORD - PWM
First | Non stop | 3 left
From 15,000 Pts + $25.6
Premium cabin
2026-11-16
ORD - PWM
First | Non stop | 9+ left
From 15,000 Pts + $25.6
Premium cabin
2026-11-17
ORD - PWM
First | Non stop | 6 left
From 15,000 Pts + $25.6
Premium cabin
2026-11-18
ORD - PWM
First | Non stop | 7 left
From 15,000 Pts + $25.6
Premium cabin
2026-11-19
ORD - PWM
First | Non stop | 5 left
From 15,000 Pts + $25.6
Premium cabin
2026-11-27
ORD - PWM
First | Non stop | 6 left
From 15,000 Pts + $25.6
Selected hotels for your next stay
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Frequently Asked Questions
The cheapest route from Chicago to Portland depends on award space, transfer bonuses, and travel dates. PointsYeah compares bank and airline programs in one place so you can find the best points and cash combinations faster.
Yes. Transferable points from Chase, Amex, Capital One, Citi, and Bilt can often be moved to airline partners for flights from Chicago to Portland.
Yes. Searching metro codes when available helps compare nearby airport combinations for flights from Chicago to Portland.
Chicago and Portland are about 902 miles (1,452 km) apart in a straight line.
Flying the 902-mile straight-line distance takes about 2h 15m in the air, estimated from typical cruising speed. Actual travel time depends on the routing; itineraries with connections take longer.
Portland is 1 hour ahead of Chicago.
Departures from Chicago: Dupage (DPA), Chicago Midway Intl (MDW), Chicago O'Hare Intl (ORD). Arrivals in Portland: Portland Intl Jetport (PWM).
Travelers searching this route also look at other popular routes into Portland, plus the return trip when we track it. Fares and award space change daily.
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