Cheap Flights from Madison to Portland
Cheap Flights from Madison to Portland
Looking for cheap flights from Madison 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 Madison to Portland vary by season, cabin, and date, but available award flights can start around 19,500–37,000 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 Madison to Portland for specific travel dates.
2026-12-18
MSN - PDX
Economy | 1 Stop | 9+ left
From 19,500 Pts + $25.1
2026-12-19
MSN - PDX
First | 1 Stop
From 34,500 Pts + $11.2
2026-11-14
MSN - PDX
First | 1 Stop | 7 left
From 37,000 Pts + $5.6
2026-11-16
MSN - PDX
First | 1 Stop | 1 left
From 37,000 Pts + $5.6
2026-11-17
MSN - PDX
First | 1 Stop | 7 left
From 37,000 Pts + $5.6
2026-11-18
MSN - PDX
First | 1 Stop | 8 left
From 37,000 Pts + $5.6
Madison to Portland flight facts
Distance
1,640 mi
2,639 km in a straight line
Estimated flight time
about 3h 45m
In the air, for the straight-line distance
Time difference
−2h
Portland is 2 hours behind Madison.
Airports in Madison
MSN · Dane County Regional Truax Field
Airports in Portland
PDX · Portland Intl
Nearby airport alternatives
Flights Milwaukee - Portland · Milwaukee is 74 mi from Madison
Flights Appleton - Portland · Appleton is 87 mi from Madison
Flights Green Bay - Portland · Green Bay is 111 mi from Madison
Flights Chicago - Portland · Chicago is 111 mi from Madison
Flights Madison - Seattle · Seattle is 129 mi from Portland
Flights Cedar Rapids - Portland · Cedar Rapids is 149 mi from Madison
Premium cabin flights from Madison to Portland
Premium cabin
2026-11-19
MSN - PDX
First | 1 Stop | 3 left
From 38,700 Pts + $5.6
Premium cabin
2026-11-07
MSN - PDX
First | 1 Stop | 4 left
From 46,800 Pts + $5.6
Premium cabin
2026-11-11
MSN - PDX
First | 1 Stop | 2 left
From 46,800 Pts + $5.6
Premium cabin
2026-11-08
MSN - PDX
First | 1 Stop | 1 left
From 49,500 Pts + $5.6
Premium cabin
2026-11-09
MSN - PDX
First | 1 Stop | 2 left
From 49,500 Pts + $5.6
Premium cabin
2026-11-13
MSN - PDX
First | 1 Stop | 9+ left
From 49,500 Pts + $5.6
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 Madison 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 Madison to Portland.
Yes. Searching metro codes when available helps compare nearby airport combinations for flights from Madison to Portland.
Madison and Portland are about 1,640 miles (2,639 km) apart in a straight line.
Flying the 1,640-mile straight-line distance takes about 3h 45m 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 Madison.
Departures from Madison: Dane County Regional Truax Field (MSN). 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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points travel planning experience. Yeah!
