Cheap flights from Portland to Chicago from $142 PDX → ORD, RFD

Found recently, and the cheapest we hold

It is also the cheapest return we hold, of any age.

What have prices looked like?

Over 24 days, 24 Sept to 11 Nov, the cheapest return we saw each day was $244 to $448.

24 days is a short history, so treat this range as an early guide.

Those were the prices on those days, not today's.

Could nearby dates be cheaper?

We hold no other 5-night return fares leaving within 3 days of 26 Dec to compare.

Every date we hold

1 fares on 1 departure dates

Found recently, and the cheapest we hold

It is also the cheapest one-way we hold, of any age.

What have prices looked like?

Over 33 days, 24 Sept to 11 Nov, the cheapest one-way we saw each day was $137 to $252.

Those were the prices on those days, not today's.

Could nearby dates be cheaper?

We hold no other one-way fares leaving within 3 days of 21 Nov to compare.

Every date we hold

5 fares on 5 departure dates

Which month looks cheapest?

November 2026 is the cheapest month — from $142.

Return

Fares 14 to 29 days before departure were typically 35% lower than 7 to 13 days before departure.

From the cheapest return each day between 24 Sept and 11 Nov (24 days), grouped by how many days ahead the flight left; one adult in economy.

Each range covers different departure dates, so this compares typical fares, not the same trip priced twice.

Prices reflect recent searches — current fares may differ.

One-way

Fares 30 to 59 days before departure were typically 6% lower than 0 to 6 days before departure.

From the cheapest one-way each day between 24 Sept and 11 Nov (33 days), grouped by how many days ahead the flight left; one adult in economy.

Each range covers different departure dates, so this compares typical fares, not the same trip priced twice.

Prices reflect recent searches — current fares may differ.

How much is a return flight from Portland to Chicago?

The cheapest return found recently is $411 with American Airlines, 26 Dec to 31 Dec, found 5 days ago.

How much is a one-way flight from Portland to Chicago?

The cheapest one-way found recently is $142 with Alaska Airlines, 21 Nov, found 3 days ago. The cheapest one-way fare on each of 5 departure dates is usually $145 to $171.

What is the cheapest month to fly from Portland to Chicago?

November 2026 is the cheapest month for a one-way, from $142, 21 Nov, found 3 days ago.

How far ahead should I book a flight from Portland to Chicago?

In 24 days of prices between 24 Sept and 11 Nov, return fares 14 to 29 days before departure were typically 35% lower than 7 to 13 days before departure. In 33 days of prices between 24 Sept and 11 Nov, one-way fares 30 to 59 days before departure were typically 6% lower than 0 to 6 days before departure.

Is there a direct flight from Portland to Chicago?

Yes, the cheapest nonstop one-way found recently is $142 with Alaska Airlines, 21 Nov, found 3 days ago.

How long is the flight from Portland to Chicago?

The cheapest nonstop one-way found recently, with Alaska Airlines on 21 Nov, takes 4 h 8 min from Portland International Airport (PDX) to O'Hare International Airport (ORD).

Which airlines have the cheapest flights from Portland to Chicago?

Between 13 Nov and 10 Jan 2027, American Airlines has the cheapest one-way on 2 of the 5 departure dates we hold, Alaska Airlines on 2 and Allegiant Air on 1.