Cheap flights from Chicago to Portland

One-way fares from $176 · CHI → PDX · prices found by travellers in the last 48 hours

Compare all dates Portland → Chicago
Cheapest fare
$176

Frontier Airlines · Tue, Nov 10

Cheapest month
November

from $176

Direct flights
Yes

American Airlines

Flight time
4h 42m

2,820 km

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Cheapest month to fly from Chicago to Portland

Lowest one-way fare per person in each month. Choose a month to see every date.

  1. November 2026 Cheapest $176
  2. December 2026 $185

Cheapest dates in November 2026

The lowest fares we've seen for each day, cheapest first.

Frontier Airlines
Depart06:30 Tue, Nov 10ORD → PDX 5h 53m · 1 stop
$176one way, per person
View deal
Frontier Airlines
Depart06:30 Sun, Nov 15ORD → PDX 5h 53m · 1 stop
$188one way, per person
View deal
Frontier Airlines
Depart17:15 Thu, Nov 12ORD → PDX 6h 53m · 1 stop
$189one way, per person
View deal
American Airlines
Depart17:05 Fri, Nov 13ORD → PDX 4h 42m · Direct
$194one way, per person
View deal
American Airlines
Depart17:00 Sat, Nov 14ORD → PDX 4h 42m · Direct
$195one way, per person
View deal
Frontier Airlines
Depart10:29 Mon, Nov 9ORD → PDX 8h 05m · 2 stops
$264one way, per person
View deal
See every date in November 2026 →

Plan the rest of your trip to Portland

Where to stay, what to do and getting around, from our travel partners.

Where to stay

Hotels in PortlandCompare places to stay on Booking.com Find hotels →

Things to do

Things to do in PortlandTours, attractions and day trips on Klook Explore →

Getting around

Airport transfer in PortlandPre-book a driver to meet you at arrivals, with Kiwitaxi Book a transfer → Car hire in PortlandCompare rental cars from major brands on EconomyBookings Compare cars →

About flights from Chicago to Portland

Chicago (CHI) and Portland (PDX) are about 2,820 km apart. Direct flights take around 4h 42m, and recent direct fares were with American Airlines. Over the next few months, one-way fares start from $176, and November 2026 is currently the cheapest month to fly.

These prices come from searches travellers made in the last 48 hours, so they move quickly. If you see a good fare, it's worth booking soon. FlightsExp is free to use: you book directly with our travel partner.

Frequently asked questions

How much is a flight from Chicago to Portland?

The cheapest one-way fare we've seen recently is $176 with Frontier Airlines, departing Tuesday, November 10, 2026. Over the coming months, the lowest fare in each month ranges from $176 to $185.

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

November 2026 currently has the lowest fares, from $176 one way.

Are there direct flights from Chicago to Portland?

Yes. Recent direct fares were with American Airlines.

How long is the flight from Chicago to Portland?

A direct flight takes about 4h 42m. Chicago and Portland are around 2,820 km apart.

Which airlines fly from Chicago to Portland?

Recent fares on this route were with Frontier Airlines and American Airlines.

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