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

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 Airport to Chicago

Looking for a cheap last-minute deal or the best return flight from Portland Airport to Chicago? If you want to travel next month, return fares start from $387. Find the lowest prices on one-way and return tickets right here.
Chicago.$387 per passenger.Departing Wed, 10 Jun, returning Wed, 15 Jul.Return flight with United.Outbound direct flight with United departs from Portland on Wed, 10 Jun, arriving in Chicago O'Hare International.Inbound direct flight with United departs from Chicago O'Hare International on Wed, 15 Jul, arriving in Portland.Price includes taxes and charges.From $387, select.
Chicago.$387 per passenger.Departing Tue, 26 May, returning Fri, 29 May.Return flight with United.Outbound direct flight with United departs from Portland on Tue, 26 May, arriving in Chicago O'Hare International.Inbound direct flight with United departs from Chicago O'Hare International on Fri, 29 May, arriving in Portland.Price includes taxes and charges.From $387, select.
Chicago.$387 per passenger.Departing Tue, 28 Apr, returning Fri, 1 May.Return flight with United.Outbound direct flight with United departs from Portland on Tue, 28 Apr, arriving in Chicago O'Hare International.Inbound direct flight with United departs from Chicago O'Hare International on Fri, 1 May, arriving in Portland.Price includes taxes and charges.From $387, select.
Chicago.$390 per passenger.Departing Wed, 18 Nov, returning Wed, 16 Dec.Return flight with United.Outbound direct flight with United departs from Portland on Wed, 18 Nov, arriving in Chicago O'Hare International.Inbound direct flight with United departs from Chicago O'Hare International on Wed, 16 Dec, arriving in Portland.Price includes taxes and charges.From $390, select.
Chicago.$401 per passenger.Departing Mon, 27 Jul, returning Wed, 29 Jul.Return flight with United.Outbound indirect flight with United, departs from Portland on Mon, 27 Jul, arriving in Chicago O'Hare International.Inbound indirect flight with United, departs from Chicago O'Hare International on Wed, 29 Jul, arriving in Portland.Price includes taxes and charges.From $401, select.
Chicago.$447 per passenger.Departing Sat, 10 Oct, returning Sat, 24 Oct.Return flight with United.Outbound direct flight with United departs from Portland on Sat, 10 Oct, arriving in Chicago O'Hare International.Inbound direct flight with United departs from Chicago O'Hare International on Sat, 24 Oct, arriving in Portland.Price includes taxes and charges.From $447, select.
Chicago.$482 per passenger.Departing Thu, 4 Jun, returning Sun, 7 Jun.Return flight with United.Outbound direct flight with United departs from Portland on Thu, 4 Jun, arriving in Chicago O'Hare International.Inbound direct flight with United departs from Chicago O'Hare International on Sun, 7 Jun, arriving in Portland.Price includes taxes and charges.From $482, select.
Chicago.$484 per passenger.Departing Sun, 5 Apr, returning Sat, 18 Apr.Return flight with United.Outbound direct flight with United departs from Portland on Sun, 5 Apr, arriving in Chicago O'Hare International.Inbound direct flight with United departs from Chicago O'Hare International on Sat, 18 Apr, arriving in Portland.Price includes taxes and charges.From $484, select.
Chicago.$493 per passenger.Departing Mon, 27 Jul, returning Wed, 29 Jul.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Portland on Mon, 27 Jul, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Wed, 29 Jul, arriving in Portland.Price includes taxes and charges.From $493, select.
Chicago.$542 per passenger.Departing Sat, 15 Aug, returning Fri, 11 Dec.Return flight with Delta.Outbound indirect flight with Delta, departs from Portland on Sat, 15 Aug, arriving in Chicago O'Hare International.Inbound indirect flight with Delta, departs from Chicago O'Hare International on Fri, 11 Dec, arriving in Portland.Price includes taxes and charges.From $542, select.
Chicago.$549 per passenger.Departing Mon, 28 Sep, returning Thu, 1 Oct.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Portland on Mon, 28 Sep, arriving in Chicago Midway.Inbound indirect flight with Southwest Airlines, departs from Chicago Midway on Thu, 1 Oct, arriving in Portland.Price includes taxes and charges.From $549, 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.
Apr
from $484
May
from $387
Jun
from $482
Jul
from $401
Aug
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Sep
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Oct
from $447
Nov
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Dec
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Jan
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Feb
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Mar
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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.

Chicago Midway

14km from central Chicago
Closest
from $404
Search flights

Chicago O'Hare International

25km from central Chicago
Cheapest
from $387
Search flights

Chicago Dupage County

51km from central Chicago
Search flights

Chicago Rockford

126km from central Chicago
Search flights

Portland to Chicago: Flight information

The things to know before you go.
Cheapest flight found$193
Cheapest month to flyApril
Average flight time2 hrs, 49 mins
Most popular airlineUnited
Average flights per week91

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 $387. 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 49 minutes is the average flight time from Portland to Chicago.
United, American Airlines and SkyWest Airlines fly direct from Portland to Chicago.
As of April 2026, there are 93 flights per week flying from Portland to Chicago.
The cheapest month to fly from Portland to Chicago is usually April.
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 $387.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Portland Airport to Chicago on Tuesday, 28 April 2026.
Yes – the average flight time is 2 hours and 49 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, United offers the cheapest flight tickets to Chicago.

How to find cheap flights to Chicago (CHIA) from Portland (PWM) in 2024

Looking for cheap tickets from Portland to Chicago? Return tickets start from $387 and one-way flights to Chicago from Portland start from $193


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 British Airways to international carriers like Emirates, we compare all major airlines along with the most popular online travel agents to find the cheapest plane tickets.
  • Compare flight deals to Chicago from Portland from over 1,000 providers. Then choose the cheapest or fastest plane tickets. Flight tickets to Chicago start from $193 one-way.
  • Flex your dates to find the best PWM-CHIA ticket prices. If you are 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 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. Airlines that fly direct include: United
    American Airlines
    SkyWest Airlines
    Republic Airways
    Envoy Air
    Air New Zealand
    Qatar Airways
    Southwest Airlines
  • 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 chance upon 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 next time you travel.
  • Search for cheap flights regardless of where you are. To get the best flight booking experience when out and about, download the app and search for plane tickets between Portland and Chicago whenever you want.

Combine your flight to Chicago from Portland with hotels and car hire

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 hire companies in one go so that you get the best car hire 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.