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Flights from Portland to Chicago
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Flights from Portland to Chicago Starting at NZD 99

We've found these cheap flights for you. You can book one-way or return flight tickets.

  • One way
  • Round-trip
      • Cheapest nonstop
        PDX07:00
        4h 7m
        Nonstop
        ORD13:07
        Wed, Jan 29|Portland - Chicago|Alaska Airlines
        NZD 154NZD 181
        15% OFF
        15% OFF
        NZD 181NZD 154

        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 NZD 154 including taxes and charges.

      • PDX07:00
        4h 7m
        Nonstop
        ORD13:07
        Wed, Jan 22|Portland - Chicago|Alaska Airlines
        NZD 169NZD 181
        7% OFF
        7% OFF
        NZD 181NZD 169

        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 NZD 169 including taxes and charges.

      • PDX15:13
        7h 50m
        1 stop
        ORD01:03
        Wed, Apr 2|Portland - Chicago|Frontier Airlines
        NZD 99NZD 181
        46% OFF
        46% OFF
        NZD 181NZD 99

        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 NZD 99 including taxes and charges.

      • PDX07:35
        14h 38m
        1 stop
        MDW00:13
        Tue, Jan 14|Portland - Chicago|Frontier Airlines
        NZD 99
        NZD 99

        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 NZD 99 including taxes and charges.

      • PDX06:32
        8h 53m
        1 stop
        ORD17:25
        Sat, Mar 1|Portland - Chicago|Frontier Airlines
        NZD 101
        NZD 101

        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 NZD 101 including taxes and charges.

      • PDX07:35
        14h 42m
        1 stop
        MDW00:17
        Tue, Feb 4|Portland - Chicago|Frontier Airlines
        NZD 101
        NZD 101

        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 NZD 101 including taxes and charges.

      • PDX07:35
        13h 2m
        1 stop
        ORD22:37
        Tue, Feb 11|Portland - Chicago|Frontier Airlines
        NZD 105
        NZD 105

        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 NZD 105 including taxes and charges.

      • PDX12:03
        10h 14m
        1 stop
        MDW00:17
        Mon, Feb 3|Portland - Chicago|Frontier Airlines
        NZD 105
        NZD 105

        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 NZD 105 including taxes and charges.

      • PDX06:32
        15h 45m
        1 stop
        MDW00:17
        Wed, Feb 19|Portland - Chicago|Frontier Airlines
        NZD 106
        NZD 106

        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 NZD 106 including taxes and charges.

      • PDX12:03
        10h 14m
        1 stop
        MDW00:17
        Mon, Feb 10|Portland - Chicago|Frontier Airlines
        NZD 106
        NZD 106

        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 NZD 106 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

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

Airlines Flying 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 NZD 99
Alaska Airlines
From NZD 154
Delta Air Lines
From NZD 173
Southwest Airlines
From NZD 187
United Airlines
From NZD 244
American Airlines
From NZD 249
Spirit Airlines
From NZD 252

Find more flights and airlines

Alternative Routes from Portland to Chicago

Searching for potential routes that might be cheaper and faster? Check out these alternative flights from Portland to Chicago.

  • Cheapest
    Frontier Airlines
    PDX
    15:13
    7h 50m
    1 transfer
    ORD
    01:03
    Portland International Airport - O'Hare International Airport
    Wed, Apr 2Frontier Airlines
    NZD 99
  • Frontier Airlines
    PDX
    07:35
    14h 38m
    1 transfer
    MDW
    00:13
    Portland International Airport - Midway International Airport
    Tue, Jan 14Frontier Airlines
    NZD 99
  • Frontier Airlines
    PDX
    07:35
    14h 38m
    1 transfer
    MDW
    00:13
    Portland International Airport - Midway International Airport
    Tue, Jan 14Frontier Airlines
    NZD 99
    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 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 NZD 447.

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

    It takes around 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 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)?

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.
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 nonstop flight priceNZD 98
Cheapest round-trip ticket priceNZD 271
Off-season for travelNovember
Peak season for travelApril
Flight distance2,816.22 km
Average flight time4 hours 54 minutes
Popular airlineAmerican Airlines

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