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

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Compare Portland to Chicago flight deals

Find the cheapest month or even day of the year to fly to Chicago

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Flight deals from Portland to Chicago

Looking for a cheap last-minute deal or the best return flight from Portland to Chicago? Find the lowest prices on one-way and return tickets right here.
Chicago.$243 per passenger.Departing Tue, 27 May, returning Wed, 28 May.Return flight with Spirit Airlines.Outbound indirect flight with Spirit Airlines, departs from Portland on Tue, 27 May, arriving in Chicago O'Hare International.Inbound indirect flight with Spirit Airlines, departs from Chicago O'Hare International on Wed, 28 May, arriving in Portland.Price includes taxes and charges.From $243, select.
Chicago.$246 per passenger.Departing Wed, 4 Jun, returning Mon, 9 Jun.Return flight with Spirit Airlines.Outbound indirect flight with Spirit Airlines, departs from Portland on Wed, 4 Jun, arriving in Chicago O'Hare International.Inbound indirect flight with Spirit Airlines, departs from Chicago O'Hare International on Mon, 9 Jun, arriving in Portland.Price includes taxes and charges.From $246, select.
Chicago.$247 per passenger.Departing Thu, 29 May, returning Mon, 2 Jun.Return flight with Spirit Airlines.Outbound indirect flight with Spirit Airlines, departs from Portland on Thu, 29 May, arriving in Chicago O'Hare International.Inbound indirect flight with Spirit Airlines, departs from Chicago O'Hare International on Mon, 2 Jun, arriving in Portland.Price includes taxes and charges.From $247, select.
Chicago.$279 per passenger.Departing Wed, 28 May, returning Sat, 31 May.Return flight with Hawaiian Airlines.Outbound direct flight with Hawaiian Airlines departs from Portland on Wed, 28 May, arriving in Chicago O'Hare International.Inbound direct flight with Hawaiian Airlines departs from Chicago O'Hare International on Sat, 31 May, arriving in Portland.Price includes taxes and charges.From $279, select.
Chicago.$297 per passenger.Departing Wed, 25 Jun, returning Tue, 1 Jul.Return flight with Spirit Airlines.Outbound indirect flight with Spirit Airlines, departs from Portland on Wed, 25 Jun, arriving in Chicago O'Hare International.Inbound indirect flight with Spirit Airlines, departs from Chicago O'Hare International on Tue, 1 Jul, arriving in Portland.Price includes taxes and charges.From $297, select.
Chicago.$317 per passenger.Departing Sun, 25 May, returning Tue, 3 Jun.Return flight with Hawaiian Airlines.Outbound direct flight with Hawaiian Airlines departs from Portland on Sun, 25 May, arriving in Chicago O'Hare International.Inbound direct flight with Hawaiian Airlines departs from Chicago O'Hare International on Tue, 3 Jun, arriving in Portland.Price includes taxes and charges.From $317, select.
Chicago.$332 per passenger.Departing Fri, 4 Jul, returning Tue, 8 Jul.Return flight with United.Outbound indirect flight with United, departs from Portland on Fri, 4 Jul, arriving in Chicago O'Hare International.Inbound indirect flight with United, departs from Chicago O'Hare International on Tue, 8 Jul, arriving in Portland.Price includes taxes and charges.From $332, select.
Chicago.$334 per passenger.Departing Fri, 29 Aug, returning Sun, 31 Aug.Return flight with United.Outbound direct flight with United departs from Portland on Fri, 29 Aug, arriving in Chicago O'Hare International.Inbound direct flight with United departs from Chicago O'Hare International on Sun, 31 Aug, arriving in Portland.Price includes taxes and charges.From $334, select.

Find the cheapest month to fly from Portland to Chicago

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Portland to Chicago flights are currently cheapest in May.
May
from $243
Jun
from $246
Jul
from $332
Aug
from $334
Sep
from $355
Oct
from $355
Nov
from $385
Dec
from $371
Jan
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Feb
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Mar
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Apr
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Direct flights from Portland to Chicago

Alternative Portland to Chicago routes

Looking for the cheapest, fastest or easiest route from Portland to Chicago? You could fly into the following airports instead.

Portland to Chicago: Flight information

The things to know before you go.
Cheapest flight found$243
Cheapest month to flyMay
Average flight time4 hrs, 1 min
Most popular airlineUnited
Average flights per week243

Finding cheap flights from Portland to Chicago: Frequently asked questions

There are 4 airports in Chicago: Chicago Midway, Chicago O'Hare International, Chicago Dupage County, and Chicago Rockford.
The best price we found for a return flight from Portland to Chicago is $243. 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 is the average flight time from Portland to Chicago.
United, Qatar Airways and American Airlines fly direct from Portland to Chicago.
As of May 2025, there are 243 flights per week flying from Portland to Chicago.
The cheapest month to fly from Portland to Chicago is usually May 2025.
If you're flying from Portland Airport, the cheapest airport near Chicago is Chicago O'Hare International – which is 25.4 km away from the centre of Chicago. We've found flights into this airport from $243.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Portland Airport to Chicago on Tuesday, 27 May 2025.
Yes – the average flight time is 4 hours.
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 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.
In May, the average temperature is usually around 13°C. July is typically the warmest month in Chicago, when it usually averages around 26°C. You can expect the least rain in January. The coldest month is January, with temperatures averaging -8°C. The rainiest month is August.
Currently, Spirit Airlines and Hawaiian Airlines offer the cheapest flight tickets to Chicago.

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

  • Take a direct flight from Portland International Airport to Chicago and you'll be in the air for an average of 4 hours 28 minutes.

  • Chicago is 2 hours ahead of Portland, where Portland International Airport is located. Chicago operates on the UTC-5 timezone.

  • The most popular route is from Portland International Airport (PDX) to O'Hare International Airport (ORD). You can select from 139 weekly services between these two airports. If you'd like to head off as soon as possible, the earliest flight from PDX to ORD is the 00:02 United service. If you prefer to travel later, the last departure is at 23:59 with Spirit Airlines.

  • To ensure you get on your flight from PDX to Chicago, leave enough time to check in and drop off your luggage. Arriving two hours before international departures and one hour before domestic flights is the general travel rule.

  • If you're flying during a popular 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 peak periods like Thanksgiving, Christmas and New Year.

  • You can catch a direct flight from Portland International Airport to Chicago. Start your journey at PDX and touch down at O'Hare International Airport (ORD).

  • These are some of the popular airlines operating direct flights from Portland International Airport to Chicago:

  • After booking your cheap tickets from Portland International Airport to Chicago, get your documents in order. A visa or passport isn't needed since you're flying within United States. As long as you have another valid proof of identity, like a driver's licence or an ID card, you're all set.

  • Located around 19 kilometres from the centre of Portland, PDX can be reached in approximately 19 minutes by car, depending on traffic. The same journey on public transport will take roughly 45 minutes.

  • Have an early flight from Portland International Airport to Chicago? Avoid rushing to the terminal (and catch some extra z's) by choosing one of these stays close to PDX:

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

  • $111 is the best price for a one-way ticket from Portland International Airport to Chicago. Return flights start at $243. These fares can change depending on availability.

  • Get cheap tickets from PDX to Chicago by booking at least 9 months ahead. According to our research, that's the sweet spot for bagging a bargain.

  • May is the cheapest month for tickets from Portland International Airport to Chicago. If you need to travel during a different time of year, the 'Whole month' tool will give you the lowest prices for every month.

  • Sign into your online account or use the app to create a Price Alert. You'll get notified right away if there's a better deal on this route. It's easy to do, and it'll save you from searching for flight tickets from PDX to Chicago every day.

  • Use the filters to tailor your flights from Portland International Airport to Chicago. Enter your ideal departure and arrival times, airlines and number of stops. Alternatively, sort your results by 'Cheapest' to see the best deals.

Airports in Chicago

O'Hare International Airport (ORD)

Chicago Midway International Airport (MDW)

Best time to go to Chicago

  • August is the busiest month to catch a flight from Portland International Airport to Chicago while February is the quietest. To work out the ideal time to go to Chicago, consider whether you like a lively atmosphere or a quieter vibe.

  • Before booking a flight from Portland International Airport to Chicago, think about the type of weather you enjoy. July is the warmest month in Chicago, with the temperature ranging from 15ºC to 29ºC.

  • January has average temperatures of between -12ºC and 3ºC. Search for cheap flights from PDX to Chicago sometime around then if you'd rather travel in cooler conditions.

More about Chicago

  • When it comes to looking for somewhere to rest your head, you'll find the most popular stays in Chicago right here. Browse these options once you've booked your flight from Portland International Airport to Chicago:

  • All great holidays should include a little sightseeing. Millennium Park, Art Institute of Chicago and LandShark Beer Garden at Navy Pier are essential stops on your Chicago itinerary.

Complete your Chicago trip with a car rental

  • Finding you a cheap flight from Portland International Airport to Chicago isn't the only trick up our sleeve. Check out our car rentals in Chicago and have more freedom to explore. We search for deals from trusted car rental providers and put them all in one place. You can instantly compare offers and then book with no fees.

Plan the rest of your trip from Portland to Chicago

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