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Flights from Portland to Chicago
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Flights from Portland to Chicago Starting at £45

Whether you’re going for a one-way or round-trip to Chicago, we’ve got you covered! Check out these different flight options from Portland below.

  • One way
  • Round-trip
      • Cheapest nonstop
        PDX07:00
        4h 7m
        Nonstop
        ORD13:07
        Wed, Jan 29|Portland - Chicago|Alaska Airlines
        £70£83
        15% OFF
        15% OFF
        £83£70

        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 £70 including taxes and charges.

      • PDX07:00
        4h 7m
        Nonstop
        ORD13:07
        Wed, Jan 22|Portland - Chicago|Alaska Airlines
        £77£83
        7% OFF
        7% OFF
        £83£77

        Choose Alaska Airlines flights from Portland to Chicago. The one-way direct flight with Alaska Airlines departs from Portland International Airport on Wed, Jan 22, arriving at O'Hare International Airport. One-way Prices start from £77 including taxes and charges.

      • PDX15:13
        7h 50m
        1 stop
        ORD01:03
        Wed, Apr 2|Portland - Chicago|Frontier Airlines
        £45£83
        46% OFF
        46% OFF
        £83£45

        Choose Frontier Airlines flights from Portland to Chicago. The one-way connecting flight with Frontier Airlines departs from Portland International Airport on Wed, Apr 2, arriving at O'Hare International Airport. One-way Prices start from £45 including taxes and charges.

      • PDX07:35
        14h 38m
        1 stop
        MDW00:13
        Tue, Jan 14|Portland - Chicago|Frontier Airlines
        £45
        £45

        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 £45 including taxes and charges.

      • PDX06:32
        8h 53m
        1 stop
        ORD17:25
        Sat, Mar 1|Portland - Chicago|Frontier Airlines
        £46
        £46

        Choose Frontier Airlines flights from Portland to Chicago. The one-way connecting flight with Frontier Airlines departs from Portland International Airport on Sat, Mar 1, arriving at O'Hare International Airport. One-way Prices start from £46 including taxes and charges.

      • PDX07:35
        14h 42m
        1 stop
        MDW00:17
        Tue, Feb 4|Portland - Chicago|Frontier Airlines
        £46
        £46

        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 £46 including taxes and charges.

      • PDX07:35
        13h 2m
        1 stop
        ORD22:37
        Tue, Feb 11|Portland - Chicago|Frontier Airlines
        £48
        £48

        Choose Frontier Airlines flights from Portland to Chicago. The one-way connecting flight with Frontier Airlines departs from Portland International Airport on Tue, Feb 11, arriving at O'Hare International Airport. One-way Prices start from £48 including taxes and charges.

      • PDX12:03
        10h 14m
        1 stop
        MDW00:17
        Mon, Feb 3|Portland - Chicago|Frontier Airlines
        £48
        £48

        Choose Frontier Airlines flights from Portland to Chicago. The one-way connecting flight with Frontier Airlines departs from Portland International Airport on Mon, Feb 3, arriving at Midway International Airport. One-way Prices start from £48 including taxes and charges.

      • PDX06:32
        15h 45m
        1 stop
        MDW00:17
        Wed, Feb 19|Portland - Chicago|Frontier Airlines
        £48
        £48

        Choose Frontier Airlines flights from Portland to Chicago. The one-way connecting flight with Frontier Airlines departs from Portland International Airport on Wed, Feb 19, arriving at Midway International Airport. One-way Prices start from £48 including taxes and charges.

      • PDX12:03
        10h 14m
        1 stop
        MDW00:17
        Mon, Feb 10|Portland - Chicago|Frontier Airlines
        £48
        £48

        Choose Frontier Airlines flights from Portland to Chicago. The one-way connecting flight with Frontier Airlines departs from Portland International Airport on Mon, Feb 10, arriving at Midway International Airport. One-way Prices start from £48 including taxes and charges.

      • PDX01:00 pm
        3h 5m
        Nonstop
        CHI02:00 pm
        Fri, Jan 17|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.

Find the best time to fly from Portland to Chicago

Price trend charts are a great way of tracking how much your flights cost in the lead up to departure and can help you choose when to book your tickets. See how prices to Chicago from Portland have changed and are set to move below.

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

Airlines Flying 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 £45
Alaska Airlines
From £70
Delta Air Lines
From £79
Southwest Airlines
From £85
United Airlines
From £111
American Airlines
From £113
Spirit Airlines
From £115

Find more flights and airlines

Alternative Routes from Portland to Chicago

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
    15:13
    7h 50m
    1 transfer
    ORD
    01:03
    Portland International Airport - O'Hare International Airport
    Wed, Apr 2Frontier Airlines
    £45
  • Frontier Airlines
    PDX
    07:35
    14h 38m
    1 transfer
    MDW
    00:13
    Portland International Airport - Midway International Airport
    Tue, Jan 14Frontier Airlines
    £45
  • Frontier Airlines
    PDX
    07:35
    14h 38m
    1 transfer
    MDW
    00:13
    Portland International Airport - Midway International Airport
    Tue, Jan 14Frontier Airlines
    £45
    Find More Flights

FAQ

  • 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 £203.

  • How long is the flight from Portland (PDX) to Chicago (CHI)?

    It takes about 4 hours 54 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)?

  • 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)?

How to find a cheap flight from Portland to Chicago

Understanding the common pitfalls when booking your flight tickets can help you save massively when it comes time to fly. We’ve listed our six essential steps to keep in mind when you’re booking flight tickets to help you find the best price.
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

Flight Information from Portland to Chicago

Cheapest direct flight price£44
Cheapest return ticket price£123
Off-season travel monthNovember
Peak season for travelApril
Flight distance2,816.22km
Average flight time4 hours 54 minutes
Popular airlineAmerican Airlines

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