Cheap Flights from Chicago to Portland from $340

Q: How much are return flights from Chicago to Portland?

The best price we found for a return flight from Chicago to Portland is $340. 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.

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

2 hours and 22 minutes is the average flight time from Chicago to Portland.

Q: Which airlines fly direct from Chicago to Portland?

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

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

As of April 2025, there are 96 flights per week flying from Chicago to Portland.

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

The cheapest month to fly from Chicago to Portland is usually April 2025.

Q: 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 Sunday, 20 April 2025 .

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

Yes – the average flight time is 2 hours and 22 minutes.

Q: 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.

Q: 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.

Q: Which is the cheapest airline to fly from Chicago to Portland with?

The cheapest airline that flies to Portland is United .

Compare Chicago to Portland flight deals

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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.

Portland.$340 per passenger.Departing Sun, 20 Apr, returning Thu, 24 Apr.Return flight with United.Outbound direct flight with United departs from Chicago O'Hare International on Sun, 20 Apr, arriving in Portland.Inbound direct flight with United departs from Portland on Thu, 24 Apr, arriving in Chicago O'Hare International.Price includes taxes and charges.From $340, select.

Portland.$350 per passenger.Departing Fri, 9 May, returning Fri, 16 May.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Chicago O'Hare International on Fri, 9 May, arriving in Portland.Inbound indirect flight with Frontier Airlines, departs from Portland on Fri, 16 May, arriving in Chicago O'Hare International.Price includes taxes and charges.From $350, select.

Portland.$364 per passenger.Departing Wed, 6 Aug, returning Fri, 15 Aug.Return flight with United.Outbound direct flight with United departs from Chicago O'Hare International on Wed, 6 Aug, arriving in Portland.Inbound direct flight with United departs from Portland on Fri, 15 Aug, arriving in Chicago O'Hare International.Price includes taxes and charges.From $364, select.

Portland.$364 per passenger.Departing Wed, 30 Apr, returning Tue, 6 May.Return flight with United.Outbound direct flight with United departs from Chicago O'Hare International on Wed, 30 Apr, arriving in Portland.Inbound direct flight with United departs from Portland on Tue, 6 May, arriving in Chicago O'Hare International.Price includes taxes and charges.From $364, select.

Portland.$364 per passenger.Departing Wed, 10 Sep, returning Fri, 12 Sep.Return flight with United.Outbound direct flight with United departs from Chicago O'Hare International on Wed, 10 Sep, arriving in Portland.Inbound direct flight with United departs from Portland on Fri, 12 Sep, arriving in Chicago O'Hare International.Price includes taxes and charges.From $364, select.

Portland.$364 per passenger.Departing Sat, 3 May, returning Sat, 10 May.Return flight with United.Outbound direct flight with United departs from Chicago O'Hare International on Sat, 3 May, arriving in Portland.Inbound direct flight with United departs from Portland on Sat, 10 May, arriving in Chicago O'Hare International.Price includes taxes and charges.From $364, select.

Portland.$381 per passenger.Departing Thu, 23 Oct, returning Wed, 29 Oct.Return flight with United.Outbound indirect flight with United, departs from Chicago O'Hare International on Thu, 23 Oct, arriving in Portland.Inbound indirect flight with United, departs from Portland on Wed, 29 Oct, arriving in Chicago O'Hare International.Price includes taxes and charges.From $381, select.

Portland.$383 per passenger.Departing Wed, 4 Jun, returning Mon, 9 Jun.Return flight with United.Outbound indirect flight with United, departs from Chicago O'Hare International on Wed, 4 Jun, arriving in Portland.Inbound indirect flight with United, departs from Portland on Mon, 9 Jun, arriving in Chicago O'Hare International.Price includes taxes and charges.From $383, 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.

Chicago to Portland: Flight information

The things to know before you go.

Cheapest flight found	$340
Cheapest month to fly	April
Average flight time	2 hrs, 23 mins
Most popular airline	United
Average flights per week	96

Finding cheap flights from Chicago to Portland: Frequently asked questions

How much are return flights from Chicago to Portland?

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

Which airlines fly direct from Chicago to Portland?

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

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

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

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

How can I find the best flight deal to Portland?

When is the best time to book flights to Portland?

Which is the cheapest airline to fly from Chicago to Portland with?

Flying from Chicago to Portland International Jetport (PWM): what you need to know

Countless 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 Jetport (PWM) departing from either of these.
2 hours 25 minutes is the average duration of a direct flight from Chicago to Portland International Jetport.
Portland International Jetport is located in Portland. The city operates in the UTC-4 timezone and is 1 hour ahead of Chicago.
The busiest route is from O'Hare International Airport (ORD) to Portland International Jetport (PWM), with 30 direct services every week. If you'd like to head off as soon as possible, the earliest flight from ORD to PWM is the 07:05 United service. If you prefer travelling later, the last departure is at 21:45 with Southwest Airlines.
For stress-free travel, arrive at the airport two hours ahead of international flights and one hour before domestic departures. This will give you enough time to catch your flight from Chicago to PWM.
Hopping on a plane during a peak time like August? High seasons (like summer, Christmas/New Year and spring break) can add another hour at check-in and security. Play things extra safe and arrive up to four hours before an international flight and two hours before a domestic departure.

Airports in Chicago

O'Hare International Airport (ORD)

Take off and land with no stops from O'Hare International Airport (ORD). Direct flights from Chicago to Portland International Jetport Airport (PWM) operate from here.
At ORD, you can choose from various airlines offering direct flights from Chicago to Portland International Jetport Airport, such as:
From central Chicago, ORD is around 40 kilometres away. Visit the official airport website or use navigation apps to find the best way to get there.
Catching an early flight from Chicago to Portland International Jetport Airport? Avoid the stress of rushing to the terminal (and catch some extra z's) by choosing one of these hotels close to O'Hare International Airport:

Chicago Midway International Airport (MDW)

Chicago Midway International Airport (MDW) has direct flights from Chicago to Portland International Jetport (PWM).
When setting off from MDW, you'll have your pick of airlines that have direct flights from Chicago to PWM. Reach cruising altitude with one of these carriers:
MDW is about 19 kilometres from central Chicago. It'll take you 21 minutes or so to get to the airport by car from the city centre. Public transport takes approximately 46 minutes.
Get a head start on your holiday with an extra night away from home. Before your flight from Chicago to PWM, unwind in one of these hotels near Chicago Midway International Airport:

About Portland International Jetport Airport (PWM)

The last thing you need is a lengthy journey to your hotel if you're getting in late on a flight from Chicago to Portland International Jetport Airport. Check in to one of these accommodation options near PWM instead:

Getting from Portland International Jetport Airport (PWM) to central Portland

Portland International Jetport Airport to central Portland takes around 13 minutes by car. It's approximately 8 kilometres away. Find out what options are available, such as car rentals, cabs or ride-sharing services.
Travelling to the centre on public transport takes roughly 38 minutes.

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

Book a one-way ticket from Chicago to Portland International Jetport Airport from $182 or travel return from just $340. Fares listed are subject to change and may differ when you make your booking.
You're more likely to score cheap tickets from Chicago to PWM when you book 8 months before your departure date. We crunched the flight price data and found that's the time fares on this route are usually at their lowest.
You'll score the best savings on your tickets from Chicago to Portland International Jetport Airport by travelling in May. Take it one step further and use the 'Whole month' search tool to see the cheapest day to fly out.
Log into your online account or use the app to create a Price Alert. We'll let you know right away if there's a new deal on this route. It's easy to do, and it'll save you time looking for flight tickets from Chicago to PWM every day.
Personalise your trip by applying filters. Adjust the duration, number of stops, and arrival and departure times to find the ideal flight from Chicago to Portland International Jetport Airport. You can also sort the results to see the 'Best,' 'Cheapest' or 'Fastest' options first.

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

It's time to plan your travel dates for your flight from Chicago to Portland International Jetport Airport. August is the most popular month to visit Portland. If you prefer a more relaxed atmosphere, go in April.
The warmest month in Portland is July, with temperatures ranging between 14ºC and 25ºC. Book your flights from Chicago to PWM in this month if you enjoy this type of weather.
Visit in January for cooler conditions. Average temperatures range between -10ºC and 3ºC. However, this destination delivers on a good time whenever you book your cheap flights from Chicago to Portland International Jetport Airport.

More about Portland

Start your Portland trip right by choosing the perfect place to stay. After booking your flight from Chicago to Portland International Jetport Airport, explore our range of accommodation options including:
One of the best ways to experience Portland is to check out its popular attractions. Some highlights include Victoria Mansion, Portland Waterfront Historic District and Osher Map Library.

Complete your Portland trip with a car rental

Get behind the wheel of one of our car rentals in Portland and see the city on your own terms. Easily compare prices from trusted rental companies in one place after booking your hotel and cheap flights from Chicago to Portland International Jetport Airport.