ORD → PDX

Find and Compare the Cheapest Ways to Fly from Chicago to Portland

Compare one-way, round-trip and flight + hotel packages from Chicago to Portland, a nonstop flight of about 4h, with fares from around 235. Nonstop fares seen from American.

Chicago to Portland flight facts

Chicago to Portland is a domestic route covering about 1,734 miles, arriving at Portland International Airport (PDX) in United States. Peak travel season in Portland runs June–August (mild, long sunny days), while November–March is usually the quietest and best-value time to visit. Nonstop fares we've tracked on this route come from American.

Key facts for flights from Chicago to Portland
Departing fromO'Hare International Airport (ORD)
Arriving atPortland International Airport (PDX)
Distance1,734 miles (2,792 km)
Nonstop flight timeAbout 4h
Nonstop airlines seenAmerican
Round-trip fares from$235 (estimate)
Cheapest monthsSeptember, February, October
Peak season in PortlandJune–August
Cheapest hotel months in PortlandNovember–March
Best time to book1 to 3 months ahead
Route info updatedOctober 16, 2026

When to visit Portland

  • Peak season

    June–August

    Mild, long sunny days

  • Shoulder season

    April–May & September–October

    Cool and crisp, fewer crowds

  • Off-peak season

    November–March

    Cold, damp and grey

Estimated round-trip fares by month, Chicago to Portland

Estimated lowest round-trip fare per month
MonthFares from
January$270
February$250
March$275
April$280
May$270
June$360
July$325
August$305
September$235
October$260
November$325
December$350

Flying from Chicago to Portland

Airlines Flying this Route

Nonstop fares we've tracked on this route come from American. Ducoffs.com compares full-service and low-cost airlines flying between Chicago and Portland in a single search, including nonstop and one-stop options, so you can weigh price against total travel time.

Best Time to Book Flights from Chicago to Portland

Fares on this route tend to be lowest in September, February, and October. For the best selection, book about 1 to 3 months before departure and stay flexible by a day or two.

Average Travel Duration

Chicago and Portland are about 1,734 miles apart. A nonstop flight takes roughly 4h; connecting itineraries usually add 2 to 5 hours.

Chicago to Portland flight questions

How can I find the absolute cheapest flight from Chicago to Portland?

The best way to secure budget rates is by comparing multiple airlines simultaneously and checking flexible dates. Ducoffs.com scans available partner networks to bring you real-time pricing options.

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

Based on typical seasonal demand, September, February, and October tend to offer the lowest fares on this route, with estimated round-trip prices starting around $235. Live prices change daily, so run a search for your exact dates.

How long is the flight from Chicago to Portland?

Chicago and Portland are about 1,734 miles apart. A nonstop flight takes roughly 4h, while connecting itineraries usually add 2 to 5 hours depending on the layover.

Which airlines fly nonstop from Chicago to Portland?

Recent nonstop fares we've tracked on this route come from American. Schedules change by season, so your live search shows every airline flying your dates.

When are hotels cheapest in Portland?

Hotel rates in Portland are usually lowest in November–March, when demand is quieter, and highest during peak season (June–August). Booking your flight and hotel together can save up to 30%.

Which airport do I fly into for Portland?

This route arrives at Portland International Airport (PDX). Your search results also show nearby airports when they offer a cheaper or faster option.

How far in advance should I book a flight to Portland?

For this route, booking about 1 to 3 months before departure usually gives the best balance of price and seat selection. Mid-week departures are often cheaper than weekend flights.

Is it cheaper to bundle flights and hotels together?

Yes. Bundling your travel components can save you up to 30% compared to booking flights and hotels separately, as airlines and properties offer exclusive package discounts.