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 10,000–10,500 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.
2026-12-05
ORD - PDX
Economy | Non stop | 9+ left
From 10,000 Pts + $5.6
2026-12-08
ORD - PDX
Economy | Non stop | 9+ left
From 10,000 Pts + $5.6
2026-12-09
ORD - PDX
Economy | Non stop | 9+ left
From 10,000 Pts + $5.6
2026-12-09
ORD - PDX
Economy | Non stop | 9+ left
From 10,000 Pts + $5.6
2026-12-09
ORD - PDX
Economy | Non stop
From 10,500 Pts + $5.6
2026-12-01
ORD - PDX
Economy | 1 Stop
From 10,500 Pts + $11.2
Chicago to Portland flight facts
Distance
1,734 mi
2,790 km in a straight line
Estimated flight time
about 4h
In the air, for the straight-line distance
Time difference
−2h
Portland is 2 hours behind Chicago.
Airports in Chicago
DPA · Dupage
MDW · Chicago Midway Intl
ORD · Chicago O'Hare Intl
Airports in Portland
PDX · Portland Intl
Nearby airport alternatives
Flights Milwaukee - Portland · Milwaukee is 73 mi from Chicago
Flights Madison - Portland · Madison is 111 mi from Chicago
Flights Chicago - Redmond-Bend · Redmond-Bend is 116 mi from Portland
Flights Chicago - Seattle · Seattle is 129 mi from Portland
Flights Grand Rapids - Portland · Grand Rapids is 142 mi from Chicago
Flights Appleton - Portland · Appleton is 166 mi from Chicago
Premium cabin flights from Chicago to Portland
Premium cabin
2026-11-05
ORD - PDX
First | Non stop | 7 left
From 25,000 Pts + $25.6
Premium cabin
2026-11-06
ORD - PDX
First | Non stop | 7 left
From 25,000 Pts + $25.6
Premium cabin
2026-11-07
ORD - PDX
First | Non stop | 1 left
From 25,000 Pts + $25.6
Premium cabin
2026-11-08
ORD - PDX
First | Non stop | 2 left
From 25,000 Pts + $25.6
Premium cabin
2026-11-09
ORD - PDX
First | Non stop | 6 left
From 25,000 Pts + $25.6
Premium cabin
2026-11-10
ORD - PDX
First | Non stop | 3 left
From 25,000 Pts + $25.6
Selected hotels for your next stay
Portland (USA)
Sentinel, an SLH Hotel
From 60,000 Pts or $174
Portland (USA)
The Ritz-Carlton, Portland
From Pts or $642
Portland, OR (USA)
The Bidwell Marriott Portland
From Pts or $113
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 1,734 miles (2,790 km) apart in a straight line.
Flying the 1,734-mile straight-line distance takes about 4h in the air, estimated from typical cruising speed. Actual travel time depends on the routing; itineraries with connections take longer.
Portland is 2 hours behind Chicago.
Departures from Chicago: Dupage (DPA), Chicago Midway Intl (MDW), Chicago O'Hare Intl (ORD). Arrivals in Portland: Portland Intl (PDX).
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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