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Find cheap one-way flights from Portland to Chicago starting at €54.

For as little as €54, you can take your next adventure to Chicago without breaking the bank. Choose between one-way and return tickets from Portland below.

  • One way
  • Round-trip
      • Cheapest nonstop
        PDX07:00
        4h 7m
        Nonstop
        ORD13:07
        Thu, Jan 23|Portland - Chicago|Alaska Airlines
        €75€89
        16% OFF
        16% OFF
        €89€75

        Choose Alaska Airlines flights from Portland to Chicago.The one-way direct flight with Alaska Airlines departs from Portland International Airport on Thu, Jan 23, arriving at O'Hare International Airport.One-way Prices start from €75 including taxes and charges.

      • PDX07:00
        4h 7m
        Nonstop
        ORD13:07
        Wed, Jan 29|Portland - Chicago|Alaska Airlines
        €83€89
        7% OFF
        7% OFF
        €89€83

        Choose Alaska Airlines flights from Portland to Chicago.The one-way direct flight with Alaska Airlines departs from Portland International Airport on Wed, Jan 29, arriving at O'Hare International Airport.One-way Prices start from €83 including taxes and charges.

      • PDX07:35
        14h 38m
        1 stop
        MDW00:13
        Tue, Jan 14|Portland - Chicago|Frontier Airlines
        €54€89
        40% OFF
        40% OFF
        €89€54

        Choose Frontier Airlines flights from Portland to Chicago.The one-way connecting flight with Frontier Airlines departs from Portland International Airport on Tue, Jan 14, arriving at Midway International Airport.One-way Prices start from €54 including taxes and charges.

      • PDX07:35
        14h 42m
        1 stop
        MDW00:17
        Wed, Jan 22|Portland - Chicago|Frontier Airlines
        €54
        €54

        Choose Frontier Airlines flights from Portland to Chicago.The one-way connecting flight with Frontier Airlines departs from Portland International Airport on Wed, Jan 22, arriving at Midway International Airport.One-way Prices start from €54 including taxes and charges.

      • PDX07:35
        14h 38m
        1 stop
        MDW00:13
        Wed, Jan 8|Portland - Chicago|Frontier Airlines
        €54
        €54

        Choose Frontier Airlines flights from Portland to Chicago.The one-way connecting flight with Frontier Airlines departs from Portland International Airport on Wed, Jan 8, arriving at Midway International Airport.One-way Prices start from €54 including taxes and charges.

      • PDX07:35
        14h 42m
        1 stop
        MDW00:17
        Tue, Feb 4|Portland - Chicago|Frontier Airlines
        €54
        €54

        Choose Frontier Airlines flights from Portland to Chicago.The one-way connecting flight with Frontier Airlines departs from Portland International Airport on Tue, Feb 4, arriving at Midway International Airport.One-way Prices start from €54 including taxes and charges.

      • PDX07:35
        14h 38m
        1 stop
        MDW00:13
        Wed, Jan 15|Portland - Chicago|Frontier Airlines
        €55
        €55

        Choose Frontier Airlines flights from Portland to Chicago.The one-way connecting flight with Frontier Airlines departs from Portland International Airport on Wed, Jan 15, arriving at Midway International Airport.One-way Prices start from €55 including taxes and charges.

      • PDX12:03
        10h 14m
        1 stop
        MDW00:17
        Mon, Jan 27|Portland - Chicago|Frontier Airlines
        €56
        €56

        Choose Frontier Airlines flights from Portland to Chicago.The one-way connecting flight with Frontier Airlines departs from Portland International Airport on Mon, Jan 27, arriving at Midway International Airport.One-way Prices start from €56 including taxes and charges.

      • PDX07:35
        14h 42m
        1 stop
        MDW00:17
        Tue, Jan 28|Portland - Chicago|Frontier Airlines
        €56
        €56

        Choose Frontier Airlines flights from Portland to Chicago.The one-way connecting flight with Frontier Airlines departs from Portland International Airport on Tue, Jan 28, arriving at Midway International Airport.One-way Prices start from €56 including taxes and charges.

      • PDX12:03
        10h 14m
        1 stop
        MDW00:17
        Thu, Jan 30|Portland - Chicago|Frontier Airlines
        €56
        €56

        Choose Frontier Airlines flights from Portland to Chicago.The one-way connecting flight with Frontier Airlines departs from Portland International Airport on Thu, Jan 30, arriving at Midway International Airport.One-way Prices start from €56 including taxes and charges.

      • PDX01:00 pm
        3h 5m
        Nonstop
        CHI02:00 pm
        Fri, Jan 3|Portland - Chicago|Alaska Airlines
        Find More Flights
        Find More Flights

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

When is the cheapest time to book flights from Portland to Chicago?

Explore the best time to buy affordable tickets to Chicago with our price trend chart, which predicts how flight prices will change in the coming weeks from previous data.

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

Cheapest airlines flights from Portland to Chicago

Which airline provides the cheapest flights from Portland to Chicago? Discover the option that best suits your travel needs before embarking on your journey.

Frontier Airlines
From €54
Alaska Airlines
From €75
Delta Air Lines
From €92
Southwest Airlines
From €100
United Airlines
From €123
American Airlines
From €137
Sun Country Airlines
From €175
Spirit Airlines
From €333

Find more flights and airlines

Find cheap flights from Portland to Chicago by different airports

Did you know that you can save money and time on an alternative route from Portland to Chicago? Check out some of the different available routes below.

  • Cheapest
    Frontier Airlines
    PDX
    07:35
    14h 38m
    1 transfer
    MDW
    00:13
    Portland International Airport - Midway International Airport
    Tue, Jan 14Frontier Airlines
    €54
  • Frontier Airlines
    PDX
    07:35
    28h 25m
    1 transfer
    ORD
    14:00
    Portland International Airport - O'Hare International Airport
    Wed, Jan 8Frontier Airlines
    €56
  • Frontier Airlines
    PDX
    07:35
    28h 25m
    1 transfer
    ORD
    14:00
    Portland International Airport - O'Hare International Airport
    Wed, Jan 8Frontier Airlines
    €56
    Find More Flights

Frequently Asked Questions

  • When are flight tickets from Portland (PDX) to Chicago (CHI) the cheapest?

    Airlines adjust prices for flights from Portland to Chicago based on the departure date and time of your selection. By analyzing data from all airlines, we've discovered that on Trip.com, you can find the lowest flight prices on Tuesdays, Wednesdays, and Saturdays.

  • How much do flights from Portland (PDX) to Chicago (CHI) cost?

    According to Trip.com's data, the lowest price is around €241.

  • How long does it take to fly from Portland (PDX) to Chicago (CHI) and what is the distance?

    It takes around 4 hours 34 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 25 km. It takes about 40 minutes by taxi.
    • The distance from Midway International Airport to downtown is about 14 km. It takes about 30 minutes by taxi.

  • 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, Hawaiian Airlines, Southwest Airlines, United Airlines, Lufthansa, Air Canada, Qatar Airways, Iberia and Swiss Airlines.

How to find a cheap flight from Portland to Chicago

If you leave it until the last minute and forget to check some of the key information when booking tickets, prices can often end up skyrocketing. Below, you can find our top tips for getting the best value flights – from changing dates to chasing deals, there are plenty ways to keep your next trip affordable.
1
Book Early
Once prices are gone, they're gone. Lock in deals while you can!
2
Compare Flight Prices
Compare prices on travel agency and airline websites.
3
Look Out for Deals
Check airline and travel agency websites for latest flight deals
4
Check One-way Fares
Buying two cheap one-way flights can sometimes be a better deal than a round-trip.
5
Try Different Dates
Flying during the week, early in the morning, or late at night can help save money.
6
Use the Trip.com App
Save up to £10 per person when booking your flights on Trip.com

Portland to Chicago Flight Information

Cheapest nonstop flight price€53
Cheapest round-trip ticket price€146
Off-season for travelNovember
Peak season for travelSeptember
Flight distance2,816.22 km
Average flight time4 hours 34 minutes
Popular airlineAlaska Airlines

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