Portland to Chicago O'Hare (PDX → ORD). We are tracking 14 fares on this route.
Cheapest tracked fare $89 · typical price $181 · you save about $92 (51%)
Cheapest fares we're tracking
Airline
Departs
Stops
Price
—
2026-11-16
1 stop
$89
—
2027-01-26
1 stop
$113
—
2027-02-02
1 stop
$113
—
2026-12-30
1 stop
$116
—
2026-10-20
1 stop
$118
—
2026-11-10
1 stop
$118
—
2026-10-29
1 stop
$118
—
2026-10-28
Direct
$135
—
2026-11-04
Direct
$135
—
2026-11-02
1 stop
$145
—
2026-10-26
1 stop
$145
—
2026-10-27
1 stop
$145
—
2026-11-03
1 stop
$145
—
2026-11-21
1 stop
$161
Could you save more?
The airport you were going to fly from is often not the cheapest one. Compare every airport in a region against each other, or check whether a multi-day stopover beats the direct fare.
How cheap can flights from Portland to Chicago O'Hare get?
The cheapest fare we have tracked on this route is $89, compared with a typical $181 for a trip of this distance.
Is it cheaper to fly to Chicago O'Hare from a different airport?
Often, yes. Fares out of secondary airports are frequently cheaper than the obvious hub, but they are the ones most likely to be missing from a normal search. Our reverse search compares every airport in a region against each other so the cheaper departure point is not hidden.
Could a stopover make Portland to Chicago O'Hare cheaper?
Sometimes. On thin long-haul routes a two-leg trip with a multi-day stopover can beat the direct fare, and occasionally a direct fare is not sold at all. Our detour search prices those routings against the direct flight.