Cheap Flight Tickets from Portland (PWM) to Chicago (CHI)

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Latest Flight Deals from Portland to Chicago

Book one-way or return flights from Portland to Chicago from as little as AU$ 63. Choose from the popular airlines below and book your flight today!

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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.

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.

Frontier Airlines

From AU$ 63

Breeze Airways

From AU$ 158

Delta Air Lines

From AU$ 173

American Airlines

From AU$ 182

United Airlines

From AU$ 223

Southwest Airlines

From AU$ 256

ANA airlines

Find more flights and airlines

Alternative Routes from Portland to Chicago

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

Cheapest
PWM
22:11
2h 46m
Direct
ORD
23:57
Portland International Jetport - O'Hare International Airport
Tue, Jun 18Frontier Airlines
AU$ 62
PWM
11:40
20h 14m
1 transfer
MDW
06:54
Portland International Jetport - Midway International Airport
Tue, May 21Frontier Airlines
AU$ 83
PWM
11:40
20h 14m
1 transfer
MDW
06:54
Portland International Jetport - Midway International Airport
Tue, May 21Frontier Airlines
AU$ 83
Find More Flights

How do I find the cheapest flights?

When are flight from Portland (PWM) 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 lowest flight prices on Tuesdays, Wednesdays, and Saturdays.
How much are flights from Portland (PWM) to Chicago (CHI) cost?
According to Trip.com's data, the lowest price is around AU$ 576.
How long is the flights from Portland (PWM) to Chicago (CHI)?
It takes about 2 hours 56 minutes to fly from Portland (PWM) 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 time does the earliest flight from Portland to Chicago depart?
The earliest flight departs from Portland (PWM) at 06:05 and arrives in Chicago (ORD) at 07:54.
What time does the latest flight from Portland to Chicago depart?
The latest flight departs from Portland (PWM) at 17:55 and arrives in Chicago (ORD) at 19:45.
What are the most popular airlines that fly from Portland (PWM) to Chicago (CHI)?
Airlines with flights from Portland (PWM) to Chicago (CHI): Emirates, United Airlines and Air New Zealand.
What's the most popular airline for direct flights from Portland (PWM) to Chicago (CHI)?
United Airlines operates 2 direct flights from Portland (PWM) 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

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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.

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Flight Information from Portland to Chicago

Cheapest direct flight price	AU$ 62
Cheapest return ticket price	AU$ 61
Off-season for travel	May
Peak season for travel	October
Flight distance	1,425.81km
Average flight time	2 hours 56 minutes
Popular airline	Delta Air Lines