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 Airport? If you want to travel next month, return fares start from £159. Find the lowest prices on one-way and return tickets right here.

Portland.£65 per passenger.Departing Wed, 29 Apr.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Chicago O'Hare International on Wed, 29 Apr, arriving in Portland.Price includes taxes and charges.From £65, select.

Portland.£73 per passenger.Departing Sun, 3 May.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Chicago O'Hare International on Sun, 3 May, arriving in Portland.Price includes taxes and charges.From £73, select.

Portland.£84 per passenger.Departing Fri, 5 Jun.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Chicago O'Hare International on Fri, 5 Jun, arriving in Portland.Price includes taxes and charges.From £84, select.

Portland.£94 per passenger.Departing Mon, 17 Aug.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Chicago O'Hare International on Mon, 17 Aug, arriving in Portland.Price includes taxes and charges.From £94, select.

Portland.£94 per passenger.Departing Sat, 25 Apr.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Sat, 25 Apr, arriving in Portland.Price includes taxes and charges.From £94, select.

Portland.£95 per passenger.Departing Sat, 9 May.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Sat, 9 May, arriving in Portland.Price includes taxes and charges.From £95, select.

Portland.£96 per passenger.Departing Sat, 4 Jul.One-way flight with Allegiant Air.Outbound indirect flight with Allegiant Air, departs from Chicago Rockford on Sat, 4 Jul, arriving in Portland.Price includes taxes and charges.From £96, select.

Portland.£114 per passenger.Departing Wed, 17 Jun.One-way flight with Alaska Airlines.Outbound direct flight with Alaska Airlines departs from Chicago O'Hare International on Wed, 17 Jun, arriving in Portland.Price includes taxes and charges.From £114, select.

Portland.£115 per passenger.Departing Sat, 11 Jul.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Sat, 11 Jul, arriving in Portland.Price includes taxes and charges.From £115, select.

Portland.£116 per passenger.Departing Tue, 17 Nov.One-way flight with United.Outbound direct flight with United departs from Chicago O'Hare International on Tue, 17 Nov, arriving in Portland.Price includes taxes and charges.From £116, select.

Portland.£116 per passenger.Departing Wed, 26 Aug.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Wed, 26 Aug, arriving in Portland.Price includes taxes and charges.From £116, select.

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 April.

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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.

Portland

6 miles from central Portland

ClosestCheapest

from £65

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Salem

45 miles from central Portland

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Chicago to Portland: Flight information

The things to know before you go.

Cheapest flight found	£65
Cheapest month to fly	April
Average flight time	4 hrs, 26 mins
Most popular airline	United
Average flights per week	404

Finding cheap flights from Chicago to Portland: Frequently asked questions

How much are return flights from Chicago to Portland?

The best price we found for a return flight from Chicago to Portland is £140. 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.

How long does it take to fly from Chicago to Portland?

4 hours and 26 minutes is the average flight time from Chicago to Portland.

Which airlines fly direct from Chicago to Portland?

United, American Airlines and Southwest Airlines fly direct from Chicago to Portland.

How many flights are there a week from Chicago to Portland?

As of April 2026, there are 193 flights per week flying from Chicago to Portland.

When is the cheapest time to fly from Chicago to Portland?

The cheapest month to fly from Chicago to Portland is usually April.

Which upcoming date is cheapest to fly from Chicago to Portland Airport on?

After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Chicago to Portland Airport on Wednesday, 29 April 2026.

Can I get a direct flight from Chicago to Portland Airport?

Yes – the average flight time is 4 hours and 26 minutes.

How can I find the best flight deal to Portland?

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.

When is the best time to book flights to Portland?

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

Start your trip planning by looking up the best place to catch your flight from Chicago to Portland International Airport (PDX). Explore the options for leaving from Chicago O'Hare International Airport (ORD) or Chicago Midway International Airport (MDW), the city's main airports.
4 hours 30 minutes is the average travel time for a direct Chicago to Portland International Airport flight.
The timezone in Portland is UTC-8, which is two hours behind Chicago. Portland International Airport is located in Portland.
The most popular route is from Chicago O'Hare International Airport (ORD) to Portland International Airport (PDX), with 51 direct services every week. If you're ready to head out sooner, the earliest flight from ORD to PDX is the 7am Alaska Airlines option. If you prefer to leave later in the day, the final departure is at 8:25pm with American Airlines.
Your flight from Chicago to PDX won't wait if you're late, so don't forget to check in on time. Arrive up to one hour in advance for domestic flights and two hours ahead when you're flying internationally.
July is a popular time to fly out. If you're taking off then or around a major holiday like July Fourth, 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

Chicago O'Hare International Airport (ORD)

Reach your destination without the detour from Chicago O'Hare International Airport (ORD). Nonstop flights from Chicago to Portland International Airport (PDX) are available from here.
Choose from a variety of airlines that offer direct flights from Chicago to Portland International Airport leaving from ORD. Reserve your trip with one of these:
The preferred airline for passengers flying between ORD and PDX is United.
The carrier with the top on-time arrival rate on this route is United.
Travelling from central Chicago to ORD takes around 45 minutes by public transport. If you ride-share, drive or get a taxi, you'll cover the 27 kms (17 miles) in 30 minutes or so, depending on traffic.
In search of a comfortable hotel near Chicago O'Hare International Airport? If you're catching an early flight from Chicago to Portland International Airport, these accommodation options will put you moments from your check-in counter:
70% of flights departing from Chicago O'Hare International Airport touch down at their destination on time.
You'll find ORD at 10000 West O'Hare.

Chicago Midway International Airport (MDW)

You can book a direct Chicago to Portland International Airport (PDX) plane ticket out of Chicago Midway International Airport (MDW). Decide if leaving from MDW is a better fit for your trip.
From MDW, direct flights from Chicago to PDX can be booked with Southwest Airlines.
Southwest Airlines ranks number one in bookings on the MDW to PDX route.
The carrier with the best on-time performance is Southwest Airlines. Its Chicago Midway International Airport to Portland International Airport flights arrive without delay 69.47% of the time.
You can arrive at MDW from central Chicago in approximately 25 minutes by car (depending on traffic). The journey by public transport takes roughly 30 minutes to cover the 16 kms (10 miles) or so.
Start your holiday sooner with an additional night away from home. Before your Chicago to PDX flight, unwind in one of these hotels near Chicago Midway International Airport:
Looking at how often flights stay on schedule, Chicago Midway International Airport has an on-time arrival performance of 76%.
You'll find MDW at 5700 South Cicero.

Chicago Rockford International Airport (RFD)

RFD is around 145 kms (90 miles) from central Chicago. Driving from the city centre to the airport takes about 1 hour 40 minutes. If you're planning to take public transport, expect a journey of around 2 hours.
Make catching an early Chicago to Portland International Airport flight one of the easiest parts of your trip. Book a room at one of these accommodation options near Chicago Rockford International Airport and get to the check-in counter without rushing:
Flights that depart from RFD make it to their destination within the expected time frame 71% of the time.
The street address of Chicago Rockford International Airport is 2 Airport Cir.

About Portland International Airport (PDX)

Consider booking a hotel near PDX if you're catching a late flight from Chicago to Portland International Airport. Settle into one of these options and get some sleep sooner:
Secure the lowest price by booking your ride around one week before your Chicago to Portland International Airport flight.
The street address for PDX is 7000 NE Airport Way.

Getting from Portland International Airport (PDX) to central Portland

Portland International Airport is about 10 kms (6 miles) from central Portland. The time it takes to get to the centre by taxi or car hire depends on the time of day. Do a little research beforehand.
Travelling on public transport will take you roughly 40 minutes.

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

£65 is the lowest price for a one-way ticket from Chicago to Portland International Airport. A return flight starts from £140. These fares may change based on availability and demand.
Don't leave things to the last minute. You're more likely to walk away with cheap flights from Chicago to PDX if you book ahead. Airlines often have some amazing early bird discounts.
Affordable Chicago to Portland International Airport tickets are easier to find when your travel dates are flexible. Try using the 'Whole month' search tool to compare fares across every month and then pick the cheapest day.
You don't need to search every day to find out if prices have dropped when you create a Price Alert. We'll notify you as soon as there's a better deal on plane tickets from Chicago to PDX.
Filters make it easier to save some cash on your flight from Chicago to Portland International Airport. Pick the departure times, airlines and number of stops that check all your boxes. Then sort the results by 'Cheapest' to bring up the lowest fares right away.

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

December is the quietest month for flights from Chicago to Portland International Airport (PDX), while July is the most popular. Pick the best time to visit Portland based on whether you want a bustling atmosphere or a more laid-back vibe.
The warmest month in Portland is August, with temperatures ranging between 12ºC and 31ºC. Book your Chicago to PDX plane ticket then if that's your idea of comfortable weather.
If you want cooler conditions, look for a cheap ticket from Chicago to Portland International Airport in January when temperatures are between -2ºC and 10ºC.

More about Portland

When it comes to searching for somewhere to rest your head, you'll find the most popular stays in Portland right here. Check out these hotels as soon as you've booked your flight from Chicago to Portland International Airport:
There are plenty of exciting things to do in Portland when you're ready to sightsee. Kick off your exploring at Portland Japanese Garden followed by Peninsula Park Rose Garden and Beyond Van Gogh Portland.

Explore more of the United States

Portland has plenty going for it, but there are so many other parts of the United States waiting to be explored. About 225 kms (140 miles) north of Portland, a visit to Seattle will fill your itinerary to the brim. Start with leading attractions like Space Needle, Pike Place Market and Seattle Skyline.
Tacoma is another sought-after destination in the United States and is around 193 kms (120 miles) north of Portland. No journey is complete without dropping by LeMay - America's Car Museum, Chihuly Bridge of Glass and Point Defiance Park.