Cheap Flights from Portland (PDX) to Chicago (ORD)

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      Compare Portland to Chicago O'Hare International flight deals

      Find the cheapest month or even day of the year to fly to Chicago O'Hare International

      Book the best Chicago O'Hare International fare with no extra fees

      Flight deals from Portland to Chicago O'Hare International

      Looking for a cheap last-minute deal or the best return flight from Portland Airport to Chicago O'Hare International Airport? If you want to travel next month, return fares start from $386. Find the lowest prices on one-way and return tickets right here.

      Find the cheapest month to fly from Portland to Chicago O'Hare International

      We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Portland to Chicago O'Hare International flights are currently cheapest in October.

      Direct flights from Portland to Chicago O'Hare International

      Air Canada
      Alaska Airlines
      American Airlines
      British Airways
      Brussels Airlines
      Finnair
      Gulf Air
      Iberia
      Lufthansa
      Malaysia Airlines
      Qatar Airways
      SWISS
      United

      Portland to Chicago O'Hare International: Alternative routes

      Compare routes from Portland to Chicago below. You may find an airport to fly into that's cheaper, faster, or easier than Chicago O'Hare International.

      Portland to Chicago: Flight information

      The things to know before you go.
      Cheapest flight found$386
      Cheapest month to flySeptember
      Average flight time4 hrs, 11 mins
      Most popular airlineAmerican Airlines
      Average flights per week221

      Finding cheap flights from Portland to Chicago O'Hare International: Frequently asked questions

      The best price we found for a return flight from Portland to Chicago O'Hare International is $386. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.
      4 hours and 11 minutes is the average flight time from Portland to Chicago O'Hare International.
      American Airlines, Qatar Airways and United fly direct from Portland to Chicago O'Hare International.
      As of September 2026, there are 244 flights per week flying from Portland to Chicago O'Hare International.
      The cheapest month to fly from Portland to Chicago O'Hare International is usually September.
      After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Portland Airport to Chicago O'Hare International Airport on Monday, 28 September 2026.
      Yes – the average flight time is 4 hours and 11 minutes.
      We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Chicago O'Hare International but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.

      We crunched all the numbers in our flight calendar and it looks like the cheapest time to book a flight to Chicago is around 40 days in advance, so don’t leave your flight to the last minute.

      Currently, Frontier Airlines and Alaska Airlines offer the cheapest flight tickets to Chicago O'Hare International.

      Flying from Portland Airport (PDX) to Chicago O'Hare International Airport (ORD): what you need to know

      • Take a direct flight from Portland Airport to Chicago O'Hare International Airport and you'll be in the air for an average of 4 hours 5 minutes.

      • Chicago's timezone is UTC-6, making Chicago two hours ahead of Portland.

      • Choose from 61 weekly Portland Airport to Chicago O'Hare International Airport flights. The 06:32 departure with American Airlines is the earliest flight you can take. United Airlines operates the last service of the day at 23:59.

      • Arriving two hours before an international flight and one hour ahead of a domestic departure are tried-and-true travel tips. Be at the airport with enough time to board your PDX to ORD flight.

      • During popular months like July, you'll want to get to the airport earlier than usual. Plan to arrive two hours before domestic departures and four hours ahead of international flights whenever you're flying during a high season in general.

      • A number of airlines offer direct flights from Portland Airport to Chicago O'Hare International Airport, so getting to Chicago (and then exploring more of the United States!) is easy. Popular carriers that fly nonstop include:

      • United tops the list for bookings on this route.

      • United is the most punctual carrier operating PDX to ORD flights. An impressive 86.32% of its services on this route arrive without delay.

      • Think about adding a stopover when booking your ticket from Portland Airport to Chicago O'Hare International Airport. Just deselect 'Direct flights only' to break up your journey, or even explore someplace new along the way. Check out these options between PDX and ORD:

        • Denver International Airport

        • Minneapolis St Paul Airport

        • St Louis Airport

      How to find the cheapest flights from Portland Airport (PDX) to Chicago O'Hare International Airport (ORD)

      • Currently, $191 is the cheapest price we've found for a one-way Portland Airport to Chicago O'Hare International Airport flight. The best price for a return ticket is $386. Bear in mind that fares may change due to demand when booking.

      • To score cheap tickets from PDX to ORD, book in advance. Airlines generally offer lower prices when flights are first released.

      • Plan your trip for May. That's the cheapest month for flights from Portland Airport to Chicago O'Hare International Airport. If your travel dates are flexible, try out the 'Whole month' tool to find the cheapest airfare across every month.

      • There's no need to check back in every day to see if fares have gone down when you create a Price Alert. We'll update you the moment a special offer becomes available on cheap flights from PDX to ORD.

      • Choose your preferred arrival and departure times, airlines and number of stops with the filters. Alternatively, sort your results by 'Cheapest' to get the best deals on flights from Portland Airport to Chicago O'Hare International Airport.

      Handy information about Portland Airport (PDX)

      • You'll find PDX at 7000 NE Airport Way.

      • 83% of flights leaving Portland Airport touch down at their destination according to schedule. With its strong performance rating, delays are unlikely when flying out of PDX.

      • To reach Portland Airport from central Portland, it takes around 20 minutes if you're going by car. This depends on traffic, however. It's approximately 19 kilometres from the airport to the city centre.

      • You can expect a journey time of about 40 minutes on public transport.

      • Have an early flight from Portland Airport to Chicago O'Hare International Airport? Avoid rushing to the terminal (and get some extra shut-eye) by picking one of these hotels close to PDX:

      Arriving at Chicago O'Hare International Airport (ORD)

      Getting from Chicago O'Hare International Airport (ORD) to central Chicago

      • ORD is located at 10000 West O'Hare.

      • Chicago O'Hare International Airport is approximately 27 kilometres from the centre of Chicago. Driving there takes about 30 minutes.

      • If you're using public transport, expect a journey of roughly 45 minutes.

      When to fly to Chicago O'Hare International Airport (ORD)

      • It's time to pick your travel dates for your flight from Portland Airport to Chicago O'Hare International Airport. July is the busiest month to visit Chicago. If you like a more low-key vibe, go in March.

      • Before locking in your flight from Portland Airport to Chicago O'Hare International Airport, think about the kind of weather you like. July is the warmest month in Chicago, with the temperature ranging from 16ºC (61ºF) to 28ºC (82ºF).

      • If you'd rather travel in cooler conditions, look for a cheap ticket from PDX to ORD in January. Temperatures average between -12ºC (10ºF) and 3ºC (37ºF) then.

      Explore more of the United States

      • Columbus is just one of the many places in the United States waiting to be explored once you've seen the sights of Chicago. Around 451 kilometres away to the south-east, top sights here include Franklin Park Conservatory and Botanical Gardens, Whetstone Park / Park of Roses and Ohio Theatre.

      • If there's time to check out another major stop in the United States, head for Indianapolis, roughly 257 kilometres south-east of Chicago. Lucas Oil Stadium, Eiteljorg Museum and The Children's Museum of Indianapolis are the start of reasons to visit.

      Prices shown on this page are estimated lowest prices only. Found in the last 12 days.