Cheap Flights from Portland to Chicago
Cheap Flights from Portland to Chicago
Looking for cheap flights from Portland to Chicago? 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 Portland to Chicago vary by season, cabin, and date, but available award flights can start around 7,500–12,500 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 Portland to Chicago for specific travel dates.
2026-11-14
PWM - ORD
Economy | Non stop | 4 left
From 7,500 Pts + $25.6
2026-11-18
PWM - ORD
Economy | Non stop | 7 left
From 7,500 Pts + $25.6
2026-11-26
PWM - ORD
Economy | Non stop | 9+ left
From 7,500 Pts + $25.6
2026-12-09
PWM - ORD
Economy | Non stop | 3 left
From 7,500 Pts + $25.6
2026-11-21
PWM - ORD
Economy | 1 Stop
From 12,000 Pts + $5.6
2026-11-09
PWM - ORD
Economy | 1 Stop | 9+ left
From 12,500 Pts + $25.6
Portland to Chicago 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
Chicago is 1 hour behind Portland.
Airports in Portland
PWM · Portland Intl Jetport
Airports in Chicago
DPA · Dupage
MDW · Chicago Midway Intl
ORD · Chicago O'Hare Intl
Nearby airport alternatives
Flights Manchester NH - Chicago · Manchester NH is 75 mi from Portland
Flights Boston - Chicago · Boston is 95 mi from Portland
Flights Bangor - Chicago · Bangor is 109 mi from Portland
Flights Bar Harbor - Chicago · Bar Harbor is 112 mi from Portland
Flights Worcester - Chicago · Worcester is 124 mi from Portland
Flights Providence - Chicago · Providence is 144 mi from Portland
Premium cabin flights from Portland to Chicago
Premium cabin
2026-11-06
PWM - ORD
First | 1 Stop | 3 left
From 25,000 Pts + $25.6
Premium cabin
2026-11-07
PWM - ORD
First | 1 Stop | 3 left
From 25,000 Pts + $25.6
Premium cabin
2026-11-10
PWM - ORD
First | 1 Stop | 2 left
From 25,000 Pts + $25.6
Premium cabin
2026-11-11
PWM - ORD
First | 1 Stop | 1 left
From 25,000 Pts + $25.6
Premium cabin
2026-11-15
PWM - ORD
First | 1 Stop | 2 left
From 25,000 Pts + $25.6
Premium cabin
2026-11-17
PWM - ORD
First | 1 Stop | 5 left
From 25,000 Pts + $25.6
Selected hotels for your next stay
Chicago (United States)
Chicago Athletic Association
From 15,000 Pts or $236
Chicago (USA)
ACME Hotel Chicago, Outset Collection by Hilton
From 28,000 Pts or $75
Chicago, IL (USA)
Waldorf Astoria Chicago
From 95,000 Pts or $407
Frequently Asked Questions
The cheapest route from Portland to Chicago 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 Portland to Chicago.
Yes. Searching metro codes when available helps compare nearby airport combinations for flights from Portland to Chicago.
Portland and Chicago 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.
Chicago is 1 hour behind Portland.
Departures from Portland: Portland Intl Jetport (PWM). Arrivals in Chicago: Dupage (DPA), Chicago Midway Intl (MDW), Chicago O'Hare Intl (ORD).
Travelers searching this route also look at other popular routes into Chicago, plus the return trip when we track it. Fares and award space change daily.
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