Cheap flight tickets from Chicago to Portland

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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 Airport? If you want to travel next month, return fares start from RM1,225. 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 September.

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 foundRM427
Cheapest month to flySeptember
Average flight time2 hrs, 26 mins
Most popular airlineAmerican Airlines
Average flights per week79

Finding cheap flights from Chicago to Portland: Frequently asked questions

The best price we found for a return flight from Chicago to Portland is RM937. 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.
2 hours and 26 minutes is the average flight time from Chicago to Portland.
American Airlines, Republic Airways and United fly direct from Chicago to Portland.
As of June 2026, there are 79 flights per week flying from Chicago to Portland.
The cheapest month to fly from Chicago to Portland is usually September.
After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Chicago to Portland Airport on Saturday, 26 September 2026.
Yes – the average flight time is 2 hours and 26 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 Jetport (PWM): What you need to know

  • Your adventure begins at one of Chicago's main airports, Chicago O'Hare International Airport (ORD) or Chicago Midway International Airport (MDW). Check out your options for booking a flight from Chicago to Portland International Jetport (PWM) jetting off from either of these.

  • Around 2 hours 25 minutes is how long you'll be in the air on a direct Chicago to Portland International Jetport flight.

  • The timezone in Portland is UTC-5, which is one hour ahead of Chicago. Portland International Jetport is located in Portland.

  • With 27 direct flights a week between the two airports, Chicago O'Hare International Airport (ORD) to Portland International Jetport (PWM) is the busiest route. United Airlines operates the earliest flight at 7:10am. If you'd like to make the most of your day before leaving, the latest flight from ORD to PWM is with American Airlines at 7:10pm.

  • Get to the airport on time so you don't miss your flight from Chicago to PWM. Be there at least two hours ahead for international flights and an hour early for domestic departures to prevent a last-minute sprint to your gate.

  • If you're going away during a peak month like July, head to the airport even earlier. You'll want to arrive up to four hours before international flights and two hours ahead of domestic departures. Security lines will be longer during holiday periods like Thanksgiving and Christmas.

Airports in Chicago

Chicago O'Hare International Airport (ORD)

  • You can find a direct flight from Chicago to Portland International Jetport (PWM) out of Chicago O'Hare International Airport (ORD).

  • When leaving from ORD, you can take a direct flight from Chicago to Portland International Jetport with United Airlines.

  • United is the airline most travellers choose for flights from ORD to PWM.

  • Among carriers on this route, United has the highest rate of on-time arrivals.

  • ORD is about 27 kilometres from central Chicago. If you're catching a taxi, driving or ride-sharing from the centre, it'll take you 30 minutes or so to get there, depending on traffic. If you're planning to take public transport, expect the travel time to be around 45 minutes.

  • Searching for a comfortable hotel close to Chicago O'Hare International Airport? If you've booked an early flight from Chicago to Portland International Jetport, these stays will have you sleeping moments from your check-in counter:

  • Of the departures from Chicago O'Hare International Airport, 70% arrive on time at their destination.

  • You'll find ORD at 10000 West O'Hare.

Chicago Midway International Airport (MDW)

  • Think about kicking off your trip from Chicago Midway International Airport (MDW). You can book a direct Chicago to Portland International Jetport (PWM) plane ticket from this hub.

  • From MDW, direct flights from Chicago to PWM are offered by Southwest Airlines.

  • Southwest Airlines is the most frequently booked airline flying from MDW to PWM.

  • If you're looking for a carrier known for its punctual service, book with Southwest Airlines. It has an exceptional on-time performance of 94.12% for flights between Chicago Midway International Airport and Portland International Jetport.

  • MDW is about 16 kilometres from central Chicago. It'll take 25 minutes or so to get to the airport by car from the city centre. Public transport takes roughly 30 minutes.

  • Got an early start? Think about staying at one of these accommodation options near Chicago Midway International Airport the day before your Chicago to PWM flight:

  • Chicago Midway International Airport has an on-time performance rate of 76%. This figure sheds light on how frequently flights departing from this airport arrive on schedule.

  • You'll find MDW at 5700 South Cicero.

Chicago Rockford International Airport (RFD)

  • The journey time to RFD from central Chicago is around 2 hours by public transport. If you're going by car, it'll take you about 1 hour 40 minutes to cover the 145 kilometres or so.

  • Stay in bed a little longer and still make your Chicago to Portland International Jetport flight with plenty of time to spare. These hotels near Chicago Rockford International Airport make departure day effortless if you're flying out first thing:

  • Flights that depart from RFD arrive at their destination as scheduled 71% of the time.

  • You'll find Chicago Rockford International Airport at 2 Airport Cir.

About Portland International Jetport (PWM)

Getting from Portland International Jetport (PWM) to central Portland

  • Central Portland is around 8 kilometres from Portland International Jetport and takes about 15 minutes to reach by car. See what your options are for making the trip into the city, whether that's with a car hire, taxi or ride-share.

  • It typically takes 30 minutes to get there using public transport.

How to find the cheapest flights from Chicago to Portland International Jetport (PWM)

  • Right now, RM427 is the lowest price we've found for a one-way ticket from Chicago to Portland International Jetport. The cheapest price for a return flight is RM937. Keep in mind fares may change due to availability at the time of booking.

  • Don't leave things to the last moment. You're more likely to find cheap flights from Chicago to PWM if you book in advance. Airlines often offer some amazing early bird discounts.

  • Affordable Chicago to Portland International Jetport tickets are easier to find if you're not locked into specific dates. Try using the 'Whole month' search function to compare fares across every month and then pick the cheapest day.

  • Never miss a deal on plane tickets from Chicago to PWM by setting up a Price Alert. We'll send you an email or push notification on the app when fares go down.

  • Lock in a cheap flight from Chicago to Portland International Jetport by using filters. Choose your ideal departure time, duration and airlines, then sort the results by 'Cheapest' for the best deals.

The best time to fly from Chicago to Portland International Jetport (PWM)

  • August is when most people book flights from Chicago to Portland International Jetport (PWM). Plan your visit to Portland in January for a quieter experience.

  • When booking your Chicago to PWM plane ticket, consider the kind of weather you prefer. July is the warmest month in Portland, with temperatures ranging from 14ºC (57ºF) to 25ºC (77ºF).

  • Search for cheap tickets from Chicago to Portland International Jetport in January if you want to travel in cooler conditions. Temperatures are at their lowest then, ranging between -10ºC (14ºF) and 3ºC (37ºF).

More about Portland

Explore more of the United States

  • Portland will leave a lasting impression, but there are so many other corners of the United States just waiting to be explored. Around 153 kilometres southwest of Portland, a trip to Boston will keep your itinerary busy. Don't miss top attractions like Museum of Fine Arts Boston, Freedom Trail and Boston Tea Party Ships & Museum.

  • Worcester is another well-known destination in the United States and is around 193 kilometres southwest of Portland. No trip is complete without a visit to Worcester Art Museum, Saint Paul’s Cathedral and Mechanics Hall.

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