Cheap Flights from Portland to Chicago from CAD 44️ 2024

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Find Portland to Chicago flights starting at CAD 44.

Book one-way or return flights from Portland to Chicago from as little as CAD 44. Choose from the popular airlines below and book your flight today!

One way
Round-trip

Crossed out prices are calculated based on the average price of the corresponding route on Trip.com.

Searching for the best last minute flight from Portland to Chicago? Find one-way or return flights that are affordable and fit your itinerary.

Trip.com monitors the ticket fares of flights from Portland to Chicago. Stay updated on price trends and snag the best deals for your upcoming trip.

Displayed prices are calculated based on the cheapest average weekly prices of the corresponding route on Trip.com.

Find Cheapest Airlines Flying from Portland to Chicago

View airlines operating flights from Portland to Chicago. Compare prices, find the option that best suits your travel needs, and enjoy a comfortable journey with a trusted airline.

Spirit Airlines

From CAD 44

Frontier Airlines

From CAD 70

Alaska Airlines

From CAD 105

American Airlines

From CAD 121

Delta Air Lines

From CAD 141

United Airlines

From CAD 166

Sun Country Airlines

From CAD 169

Southwest Airlines

From CAD 228

Jetblue Airways

From CAD 819

ANA airlines

Find more flights and airlines

Alternative Routes for Portland to Chicago Flights

Discover different routes, airlines, and transfers and find the best alternative flights for your journey from Portland to Chicago.

Cheapest
PDX
23:30
3h 50m
Direct
ORD
05:20
Portland International Airport - O'Hare International Airport
Sat, May 11Spirit Airlines
CAD 44
PDX
00:59
19h 6m
1 transfer
MDW
22:05
Portland International Airport - Midway International Airport
Tue, Apr 30Frontier Airlines
CAD 78
PDX
08:00
11h 8m
1 transfer
RFD
21:08
Portland International Airport - Chicago Rockford International Airport
Thu, May 2Alaska Airlines
CAD 472
PDX
08:00
11h 8m
1 transfer
RFD
21:08
Portland International Airport - Chicago Rockford International Airport
Thu, May 2Alaska Airlines
CAD 472
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How do I find the cheapest flights?

When are flight tickets from Portland (PDX) to Chicago (CHI) the cheapest?
Airlines adjust prices for flights from Portland to Chicago based on the date and time of your booking. By analyzing data from all airlines, on Trip.com, you can find the cheapest flight prices on Tuesdays, Wednesdays, and Saturdays.
How much are flights from Portland (PDX) to Chicago (CHI) cost?
According to Trip.com's data, the lowest price is around CAD 413.
How long is the flight from Portland (PDX) to Chicago (CHI)?
It takes about 4 hours 15 minutes to fly from Portland (PDX) to Chicago (CHI).
What is the transportation method from the main airport to downtown in Chicago?
- The distance from O'Hare International Airport to downtown is about 25km, by taxi about 40 minutes.
- The distance from Midway International Airport to downtown is about 14km, by taxi about 30 minutes.
What are the most popular airlines that fly from Portland (PDX) to Chicago (CHI)?
Airlines with flights from Portland (PDX) to Chicago (CHI): Brussels Airlines, Southwest Airlines, Scandinavian Airlines, United Airlines, Lufthansa, Air Canada, Gulf Air, American Airlines, Qatar Airways and Iberia.
What's the most popular airline for direct flights from Portland (PDX) to Chicago (CHI)?
American Airlines operates 1 direct flights from Portland (PDX) to Chicago (CHI).
How many airports in Chicago (CHI)?
There are 5 airport(s) in Chicago (CHI): Chicago Du Page County Airport, Midway International Airport, O'Hare International Airport, Chicago Palwaukee Airport and Chicago Rockford International Airport.

How to find a cheap flight from Portland to Chicago

Wait until the last minute and flight costs are often sky-high. Plan ahead, book the right way, and your savings can soar. We have loads of saving tips to help you find a cheap flight from Portland to Chicago. Book your flights at the right time and save more.

Book Early

Once prices are gone, they're gone. Lock in deals while you can!

Compare Flight Prices

Compare prices on travel agency and airline websites.

Look Out for Deals

Check airline and travel agency websites for latest flight deals

Check One-way Fares

Buying two cheap one-way flights can sometimes be a better deal than a round-trip.

Try Different Dates

Flying during the week, early in the morning, or late at night can help save money.

Use the Trip.com App

Save up to £10 per person when booking your flights on Trip.com

Flight Information for Portland to Chicago Flights

Cheapest direct flight price	CAD 43
Cheapest return ticket price	CAD 94
Cheapest month	February
Peak season for travel	October
Flight distance	2,816.22km
Average flight time	4 hours 15 minutes
Popular airline	Alaska Airlines