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Cheap flights from Portland to Chicago

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Flight deals from Portland to Chicago

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

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Find the cheapest month to fly from Portland to Chicago

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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 foundC$421
Cheapest month to flyMay
Average flight time2 hrs, 43 mins
Most popular airlineUnited
Average flights per week126

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 round-trip flight from Portland to Chicago is C$421. 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 43 minutes is the average flight time from Portland to Chicago.
United, American Airlines and Republic Airways fly direct from Portland to Chicago.
There are 126 flights per week flying from Portland to Chicago, as of April 2024.
The cheapest month to fly from Portland to Chicago is usually May.
If you're flying from Portland Airport, the cheapest airport near Chicago is Chicago Midway – which is 14.5 km away from the center of Chicago. We've found flights to this airport from C$421.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Portland Airport to Chicago on Tuesday, May 28, 2024.
Yes – the average flight time is 2 hours and 43 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 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 April, the average temperature is usually around 8°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, Delta offers the cheapest flight tickets to Chicago.

How to find cheap flights to Chicago from Portland

Looking for cheap tickets from Portland to Chicago? Here are a few tips on how to secure the best flight price and make your journey as smooth as possible.

  • Simply hit "search." From Delta Air Lines to international carriers like Emirates, we compare all major airlines along with the most popular online travel agents to find the cheapest plane tickets from Portland to Chicago. And with us, there are no hidden fees – what you see is what you pay.
  • Compare flight deals to Chicago from Portland from over 1,000 providers. Then choose the cheapest plane tickets or fastest journeys.
  • Flex your dates to find the best Portland–Chicago ticket prices. If you're flexible when it comes to your travel dates, use Skyscanner's "Whole month" tool to find the cheapest month, and even day to fly to Chicago from Portland.
  • Set up a Price Alert. You can easily track the fare of your cheap Portland–Chicago flights by creating an alert. Whenever prices go down or up, you'll get an email or push notification to help make sure you get the best possible flight deal.
  • Fly without stops. Only interested in direct flights between Portland and Chicago? Make sure to tick "Direct flights only" when performing a search. If there are direct flights available on the route, these will appear in the results.
  • Find the cheapest Business Class flights from Portland and Chicago. We scour the Internet for the best Business, Premium Economy and First Class flight fares to Chicago, too. Check the difference in price as you search – you might just stumble on a last-minute low fare. Note that not all cabin classes are available for every destination or airline.
  • Include nearby airports in your search. Widen your search for Portland to Chicago flight deals by selecting the "add nearby airports" option. This will allow you to see flight prices for all the nearest airports at your departure point and your destination and could help you save the next time you travel.

    • Combine your flight to Chicago from Portland with hotels and car rental

    Once you've secured your cheap flight ticket from Portland to Chicago, discover the best prices and exclusive rates for hotels in Chicago or nearby. You can also compare hundreds of car rental companies at once so you get the best car rental price for your trip.


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.