Portland to Chicago flights

Routavio compares airline fares from several flight booking sites. The lowest one-way fare it found for Portland to Chicago is €176 (checked on 16 Oct 2026).

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Lowest observed

€176

Cheapest month

October 2026

Last checked

29 Oct 2026

Observed fares. Prices may change.

Your next trip, last seen at €226

Lowest observed

25 - 29 Nov 2026

1 stop · 4 nights

Cheapest observed day · Last checked: 22 Oct 2026

When to fly

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The lowest fare we observed for each month. Open a month to see its days, then pick your outbound and return. A day with no price is one we will search for you.

Round-trip fare

Prices are for observed departure and return date pairs. No data does not mean no flights.

Lowest observed: €176, departing 29 Oct 2026 (Last checked: 16 Oct 2026)One-way fareCheck live prices for this route
Airlines seen: Alaska Airlines, United Airlines, Southwest Airlines, American Airlines, Frontier Airlines
Reported fastest flight: 4h 04m
Non-stop: Yes

Short answer

Routavio has seen Alaska Airlines fares from Portland to Chicago, non-stop. The lowest fare Routavio's own searches returned is €176, seen on 16 Oct 2026. October 2026 is the cheapest month in our observations, at €176. These are prices Routavio's searches returned on the dates shown, not quotes; run a live search for today's fare.

About this route

Explore the fares we observed from Portland to Chicago. Prices move often, so pick your dates to see the latest options.

Route distance: 2,824 km
Reported fastest flight: 4h 04m
Alternative airports: CGX, DPA, MDW, PWK, RFD

Route-level information; individual journeys vary.
Published schedules report non-stop service with Alaska Airlines, United Airlines, Southwest Airlines. Check current timetables.

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Observed, not guaranteed

Every price is a fare we actually saw, and it may change at any time.

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How our prices work

Airport to city: straight-line distance

Portland International Airport (PDX) → Portland, city gazetteer reference point (45.5051, -122.6750): ≈ 11 km.
Chicago Midway International Airport (MDW) → Chicago, city gazetteer reference point (41.8781, -87.6298): ≈ 14 km.
Chicago O'Hare International Airport (ORD) → Chicago, city gazetteer reference point (41.8781, -87.6298): ≈ 25 km.
Chicago Rockford International Airport (RFD) → Chicago, city gazetteer reference point (41.8781, -87.6298): ≈ 126 km.

Approximate distances calculated from coordinates, not road distances or travel times. These airports serve the city; they are not confirmed endpoints of an offer.