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

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Flight deals from Chicago to Portland

Looking for a cheap last-minute deal or the best return flight from Chicago to Portland? Find the lowest prices on one-way and return tickets right here.

Find the cheapest month to fly from Chicago to Portland

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

Direct flights from Chicago to Portland

Chicago to Portland: Alternative routes

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

Chicago to Portland: Flight information

The things to know before you go.
Cheapest flight found$249
Cheapest month to flyMay
Average flight time4 hrs, 27 mins
Most popular airlineUnited
Average flights per week158

Finding cheap flights from Chicago to Portland: Frequently asked questions

The best price we found for a return flight from Chicago to Portland is $249. 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 27 minutes is the average flight time from Chicago to Portland.
United, American Airlines and Southwest Airlines fly direct from Chicago to Portland.
As of May 2025, there are 158 flights per week flying from Chicago to Portland.
The cheapest month to fly from Chicago to Portland is usually May 2025.
After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Chicago to Portland Airport on Friday, 16 May 2025.
Yes – the average flight time is 4 hours and 27 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 Portland 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 Portland is around 40 days in advance, so don’t leave your flight to the last minute.

Travelling from Chicago to Portland International Airport (PDX): what you need to know

  • All great adventures start at one of Chicago's main airports, O'Hare International Airport (ORD) or Chicago Midway International Airport (MDW). Explore the options for booking a flight from Chicago to Portland International Airport (PDX) leaving from either of these.

  • The average length of a direct flight from Chicago to Portland International Airport is 4 hours 28 minutes.

  • The timezone in Portland is UTC-7, which is 2 hours behind Chicago. Portland International Airport is located in Portland.

  • O'Hare International Airport (ORD) to Portland International Airport (PDX) is the most popular route. There are 143 direct departures a week to choose from. If you prefer a later start to the day, hop on the last flight with Southwest Airlines at 22:50. Choose the first ORD to PDX departure with Alaska Airlines at 07:00 if you want to get going earlier.

  • Arriving two hours before an international flight and one hour ahead of a domestic departure are travel rules worth sticking to. Show up at the airport on time to catch your flight from Chicago to PDX.

  • August is a popular time to fly out. If you're heading away then or during a major holiday like Christmas or Thanksgiving, get there even earlier. Aim for at least two hours ahead for domestic flights and up to four hours for international journeys.

Airports in Chicago

O'Hare International Airport (ORD)

  • You can find a direct flight from Chicago to Portland International Airport (PDX) departing from O'Hare International Airport (ORD).

  • You'll have your pick of airlines operating direct flights from Chicago to Portland International Airport departing from ORD. Book your seat with one of these:

  • ORD is around 40 kilometres from the centre of Chicago. To work out how to get there, use Google Maps. This essential traveller tool will give you the fastest route and your public transport options.

  • In search of a handy hotel close to O'Hare International Airport? If you're boarding an early flight from Chicago to Portland International Airport, these stays will put you moments from your check-in counter:

Chicago Midway International Airport (MDW)

  • Looking for more options for a direct flight from Chicago to Portland International Airport (PDX)? Check out the fares departing from Chicago Midway International Airport (MDW).

  • You have a choice of airlines that have direct flights from Chicago to PDX departing from MDW. Jet off with any of these carriers and skip the connections:

  • On public transport, you can travel from central Chicago to MDW in around 46 minutes. The airport is roughly 19 kilometres away, and making the journey by car takes approximately 21 minutes.

  • You're off on holiday, so why not book another night away? Think about kicking back in one of these hotels near Chicago Midway International Airport the day before your flight from Chicago to PDX:

About Portland International Airport (PDX)

Getting from Portland International Airport (PDX) to central Portland

  • Portland International Airport is approximately 19 kilometres from the centre of Portland. With your own car rental or if you take a cab, the drive is around 19 minutes.

  • It takes around 45 minutes to get there by public transport.

How to find the cheapest flights from Chicago to Portland International Airport (PDX)

  • For a one-way ticket from Chicago to Portland International Airport, $128 is the best price we've seen. You can also book a return trip from just $249. These are currently the lowest fares but could change depending on availability.

  • Get flight tickets from Chicago to PDX by booking at least 8 months ahead. According to flight price data, that's the sweet spot for landing a bargain.

  • To score the best deal on your tickets from Chicago to Portland International Airport, schedule your trip for May (it's when flights are cheapest). Got flexible travel dates? Use the 'Whole month' search function to zero in on the most affordable day to fly.

  • Set up a Price Alert and keep an eye on changes on this route through push notifications or email. You'll know straight away when fares go down. Timing is key for finding flight tickets from Chicago to PDX.

  • Use the filters to tailor your flights from Chicago to Portland International Airport. Simply enter your preferred departure and arrival times, airlines and number of stops. You can also sort your results by 'Cheapest' to get the best deals.

The best time to fly from Chicago to Portland International Airport (PDX)

  • It's time to choose your dates for your flight from Chicago to Portland International Airport. July is the busiest month for a trip to Portland. If you like a more peaceful vibe, go in May.

  • Think about the kind of weather that'll work with your plans for Portland. The warmest month is August. Lock in your flights from Chicago to PDX sometime then and you can expect temperatures of between 12ºC and 31ºC.

  • Travel in December if you want cooler conditions. Average temperatures range between 0ºC and 9ºC. However, this city promises a good time whenever you book your cheap flights from Chicago to Portland International Airport.

More about Portland

  • Start your Portland trip off on the right foot by choosing the ideal place to stay. After booking your flight from Chicago to Portland International Airport, explore our range of hotels including:

  • There are so many things to discover in this city it can be tricky to work out where to begin. Pioneer Courthouse Square, Portland Japanese Garden and Pittock Mansion are leading attractions which should feature on any good Portland itinerary.

Complete your Portland trip with a car rental

  • Hop behind the wheel of one of our car rentals in Portland and see the sights at your own pace. Easily compare rates from trusted providers in one go after booking your hotel and cheap flights from Chicago to Portland International Airport.

Prices shown on this page are estimated lowest prices only. Found in the last 45 days.