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Cheap Flights from Portland to Chicago
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Cheap Flights from Portland to Chicago starting at S$ 76

Discover our range of affordable one-way and round-trip flights from Portland to Chicago and kick-start your next adventure today!

  • One way
  • Round-trip
      • Cheapest nonstop
        PDX07:00
        4h 7m
        Nonstop
        ORD13:07
        Thu, Jan 23|Portland - Chicago|Alaska Airlines
        S$ 107S$ 127
        16% OFF
        16% OFF
        S$ 127S$ 107

        Fly from Portland to Chicago on Thu, Jan 23 with Alaska Airlines. One-way direct flights with Alaska Airlines depart Portland International Airport and arrive O'Hare International Airport starting at S$ 107 including taxes and charges.

      • PDX07:00
        4h 7m
        Nonstop
        ORD13:07
        Wed, Jan 29|Portland - Chicago|Alaska Airlines
        S$ 118S$ 127
        7% OFF
        7% OFF
        S$ 127S$ 118

        Fly from Portland to Chicago on Wed, Jan 29 with Alaska Airlines. One-way direct flights with Alaska Airlines depart Portland International Airport and arrive O'Hare International Airport starting at S$ 118 including taxes and charges.

      • PDX07:35
        14h 38m
        1 stop
        MDW00:13
        Tue, Jan 14|Portland - Chicago|Frontier Airlines
        S$ 76S$ 127
        40% OFF
        40% OFF
        S$ 127S$ 76

        Fly from Portland to Chicago on Tue, Jan 14 with Frontier Airlines. One-way connecting flights with Frontier Airlines depart Portland International Airport and arrive Midway International Airport starting at S$ 76 including taxes and charges.

      • PDX07:35
        14h 42m
        1 stop
        MDW00:17
        Wed, Jan 22|Portland - Chicago|Frontier Airlines
        S$ 76
        S$ 76

        Fly from Portland to Chicago on Wed, Jan 22 with Frontier Airlines. One-way connecting flights with Frontier Airlines depart Portland International Airport and arrive Midway International Airport starting at S$ 76 including taxes and charges.

      • PDX07:35
        14h 38m
        1 stop
        MDW00:13
        Wed, Jan 8|Portland - Chicago|Frontier Airlines
        S$ 77
        S$ 77

        Fly from Portland to Chicago on Wed, Jan 8 with Frontier Airlines. One-way connecting flights with Frontier Airlines depart Portland International Airport and arrive Midway International Airport starting at S$ 77 including taxes and charges.

      • PDX07:35
        14h 42m
        1 stop
        MDW00:17
        Tue, Feb 4|Portland - Chicago|Frontier Airlines
        S$ 77
        S$ 77

        Fly from Portland to Chicago on Tue, Feb 4 with Frontier Airlines. One-way connecting flights with Frontier Airlines depart Portland International Airport and arrive Midway International Airport starting at S$ 77 including taxes and charges.

      • PDX07:35
        14h 38m
        1 stop
        MDW00:13
        Wed, Jan 15|Portland - Chicago|Frontier Airlines
        S$ 78
        S$ 78

        Fly from Portland to Chicago on Wed, Jan 15 with Frontier Airlines. One-way connecting flights with Frontier Airlines depart Portland International Airport and arrive Midway International Airport starting at S$ 78 including taxes and charges.

      • PDX12:03
        10h 14m
        1 stop
        MDW00:17
        Mon, Jan 27|Portland - Chicago|Frontier Airlines
        S$ 79
        S$ 79

        Fly from Portland to Chicago on Mon, Jan 27 with Frontier Airlines. One-way connecting flights with Frontier Airlines depart Portland International Airport and arrive Midway International Airport starting at S$ 79 including taxes and charges.

      • PDX07:35
        14h 42m
        1 stop
        MDW00:17
        Tue, Jan 28|Portland - Chicago|Frontier Airlines
        S$ 79
        S$ 79

        Fly from Portland to Chicago on Tue, Jan 28 with Frontier Airlines. One-way connecting flights with Frontier Airlines depart Portland International Airport and arrive Midway International Airport starting at S$ 79 including taxes and charges.

      • PDX12:03
        10h 14m
        1 stop
        MDW00:17
        Thu, Jan 30|Portland - Chicago|Frontier Airlines
        S$ 79
        S$ 79

        Fly from Portland to Chicago on Thu, Jan 30 with Frontier Airlines. One-way connecting flights with Frontier Airlines depart Portland International Airport and arrive Midway International Airport starting at S$ 79 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.

Cheapest 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 lowest average weekly prices of the corresponding route on Trip.com.

Cheapest 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 S$ 76
Alaska Airlines
From S$ 107
Delta Air Lines
From S$ 131
Southwest Airlines
From S$ 142
United Airlines
From S$ 174
American Airlines
From S$ 194
Sun Country Airlines
From S$ 247
Spirit Airlines
From S$ 472

Find more flights and airlines

Alternative Routes from Portland to Chicago

There are various non-direct routes from Portland to Chicago which could be cheaper and faster! Check out these alternative options to see if they could work for your trip.

  • Cheapest
    Frontier Airlines
    PDX
    07:35
    14h 38m
    1 transfer
    MDW
    00:13
    Portland International Airport - Midway International Airport
    Tue, Jan 14Frontier Airlines
    S$ 76
  • Frontier Airlines
    PDX
    07:35
    28h 25m
    1 transfer
    ORD
    14:00
    Portland International Airport - O'Hare International Airport
    Wed, Jan 8Frontier Airlines
    S$ 80
  • Frontier Airlines
    PDX
    07:35
    28h 25m
    1 transfer
    ORD
    14:00
    Portland International Airport - O'Hare International Airport
    Wed, Jan 8Frontier Airlines
    S$ 80
    Find More Flights

Frequently Asked Questions

  • When to buy 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 is a flight from Portland (PDX) to Chicago (CHI) cost?

    According to Trip.com's data, the lowest price is around S$ 341.

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

    It takes about 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 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, Hawaiian Airlines, Southwest Airlines, United Airlines, Lufthansa, Air Canada, Qatar Airways, IBERIA and Swiss Airlines.

  • 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?

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

Find cheapest flight ticket from Portland to Chicago

Cheapest direct flight priceS$ 75
Cheapest return ticket priceS$ 206
Off-season for travelNovember
Peak season for travelSeptember
Flight distance2,816.22km
Average flight time4 hours 34 minutes
Popular airlineAlaska Airlines

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