Cheap Flights from Portland to Chicago
Compare Portland to Chicago flight deals
Find the cheapest month or even day of the year to fly to Chicago
Book the best Chicago fare with no extra fees
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.Don’t miss a great deal
Stay one step ahead. Find the best value travel with the latest deals, tips and news.
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 August.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.Finding cheap flights from Portland to Chicago: Frequently asked questions
How to find cheap flights to Chicago (CHI) from Portland (PWM)in 2024
Looking for cheap tickets from Portland to Chicago? Return tickets start from 121 € and one-way flights to Chicago from Portland start from 45 €
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 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 or fastest plane tickets. Flight tickets to Chicago start from 45 € one-way.
- 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.
- Flex your dates to find the best PWM-CHI 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.
- 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
Envoy Air
Republic Airways
Air New Zealand
Southwest Airlines
SkyWest Airlines
Emirates - 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.
- Flexible on when you travel? The cheapest month to fly from Portland to Chicago is August.
- 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.