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Flights from Chicago to Portland
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Flights from Chicago to Portland Starting at NZD 94

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

  • One way
  • Round-trip
      • Cheapest nonstop
        ORD11:10
        2h 32m
        Nonstop
        PWM14:42
        Thu, Jan 16|Chicago - Portland|United Airlines
        NZD 364NZD 391
        7% OFF
        7% OFF
        NZD 391NZD 364

        Choose United Airlines flights from Chicago to Portland. The one-way direct flight with United Airlines departs from O'Hare International Airport on Thu, Jan 16, arriving at Portland International Jetport. One-way Prices start from NZD 364 including taxes and charges.

      • ORD11:10
        2h 32m
        Nonstop
        PWM14:42
        Thu, Feb 6|Chicago - Portland|United Airlines
        NZD 364NZD 391
        7% OFF
        7% OFF
        NZD 391NZD 364

        Choose United Airlines flights from Chicago to Portland. The one-way direct flight with United Airlines departs from O'Hare International Airport on Thu, Feb 6, arriving at Portland International Jetport. One-way Prices start from NZD 364 including taxes and charges.

      • ORD10:59
        8h 13m
        1 stop
        PWM20:12
        Mon, Feb 3|Chicago - Portland|Frontier Airlines
        NZD 94NZD 391
        76% OFF
        76% OFF
        NZD 391NZD 94

        Choose Frontier Airlines flights from Chicago to Portland. The one-way connecting flight with Frontier Airlines departs from O'Hare International Airport on Mon, Feb 3, arriving at Portland International Jetport. One-way Prices start from NZD 94 including taxes and charges.

      • MDW11:33
        7h 39m
        1 stop
        PWM20:12
        Mon, Jan 27|Chicago - Portland|Frontier Airlines
        NZD 97
        NZD 97

        Choose Frontier Airlines flights from Chicago to Portland. The one-way connecting flight with Frontier Airlines departs from Midway International Airport on Mon, Jan 27, arriving at Portland International Jetport. One-way Prices start from NZD 97 including taxes and charges.

      • MDW11:33
        7h 39m
        1 stop
        PWM20:12
        Mon, Jan 13|Chicago - Portland|Frontier Airlines
        NZD 99
        NZD 99

        Choose Frontier Airlines flights from Chicago to Portland. The one-way connecting flight with Frontier Airlines departs from Midway International Airport on Mon, Jan 13, arriving at Portland International Jetport. One-way Prices start from NZD 99 including taxes and charges.

      • ORD10:59
        8h 13m
        1 stop
        PWM20:12
        Fri, Jan 10|Chicago - Portland|Frontier Airlines
        NZD 109
        NZD 109

        Choose Frontier Airlines flights from Chicago to Portland. The one-way connecting flight with Frontier Airlines departs from O'Hare International Airport on Fri, Jan 10, arriving at Portland International Jetport. One-way Prices start from NZD 109 including taxes and charges.

      • ORD10:59
        8h 13m
        1 stop
        PWM20:12
        Fri, Jan 24|Chicago - Portland|Frontier Airlines
        NZD 114
        NZD 114

        Choose Frontier Airlines flights from Chicago to Portland. The one-way connecting flight with Frontier Airlines departs from O'Hare International Airport on Fri, Jan 24, arriving at Portland International Jetport. One-way Prices start from NZD 114 including taxes and charges.

      • ORD16:18
        26h 54m
        1 stop
        PWM20:12
        Sun, Jan 26|Chicago - Portland|Frontier Airlines
        NZD 128
        NZD 128

        Choose Frontier Airlines flights from Chicago to Portland. The one-way connecting flight with Frontier Airlines departs from O'Hare International Airport on Sun, Jan 26, arriving at Portland International Jetport. One-way Prices start from NZD 128 including taxes and charges.

      • MDW17:52
        15h 31m
        1 stop
        PWM10:23
        Thu, Jan 2|Chicago - Portland|Frontier Airlines
        NZD 140
        NZD 140

        Choose Frontier Airlines flights from Chicago to Portland. The one-way connecting flight with Frontier Airlines departs from Midway International Airport on Thu, Jan 2, arriving at Portland International Jetport. One-way Prices start from NZD 140 including taxes and charges.

      • MDW18:49
        23h 2m
        1 stop
        PWM18:51
        Sat, Jan 4|Chicago - Portland|Frontier Airlines
        NZD 143
        NZD 143

        Choose Frontier Airlines flights from Chicago to Portland. The one-way connecting flight with Frontier Airlines departs from Midway International Airport on Sat, Jan 4, arriving at Portland International Jetport. One-way Prices start from NZD 143 including taxes and charges.

      • CHI01:00 pm
        3h 5m
        Nonstop
        PWM02:00 pm
        Fri, Jan 3|Chicago - Portland|United 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 Chicago to Portland

We monitor flight fares to help you find the best deals effortlessly

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

Airlines Flying from Chicago to Portland

Compare prices, find the option that best suits your travel needs, and enjoy a comfortable journey with a trusted airline.

Frontier Airlines
From NZD 94
American Airlines
From NZD 160
Delta Air Lines
From NZD 184
United Airlines
From NZD 242
Southwest Airlines
From NZD 327
Jetblue Airways
From NZD 391
Spirit Airlines
From NZD 1,277

Find more flights and airlines

Alternative Routes from Chicago to Portland

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

  • Cheapest
    Frontier Airlines
    ORD
    10:59
    8h 13m
    1 transfer
    PWM
    20:12
    O'Hare International Airport - Portland International Jetport
    Mon, Feb 3Frontier Airlines
    NZD 94
  • Frontier Airlines
    MDW
    11:33
    7h 39m
    1 transfer
    PWM
    20:12
    Midway International Airport - Portland International Jetport
    Mon, Jan 27Frontier Airlines
    NZD 97
  • Frontier Airlines
    MDW
    11:33
    7h 39m
    1 transfer
    PWM
    20:12
    Midway International Airport - Portland International Jetport
    Mon, Jan 27Frontier Airlines
    NZD 97
    Find More Flights

FAQ

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

    Airlines adjust prices for flights from Chicago to Portland 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 Chicago (CHI) to Portland (PWM) cost?

    According to Trip.com's data, the lowest price is around NZD 576.

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

    It takes around 2 hours 27 minutes to fly from Chicago (CHI) to Portland (PWM).

  • What are the most popular airlines that fly from Chicago (CHI) to Portland (PWM)?

    Airlines with flights from Chicago (CHI) to Portland (PWM): Emirates, Air New Zealand and United Airlines.

How to find a cheap flight from Chicago to Portland

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 Chicago to Portland. 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 Chicago to Portland

Cheapest nonstop flight priceNZD 93
Cheapest round-trip ticket priceNZD 468
Off-season for travelJanuary
Peak season for travelMarch
Flight distance1,425.81 km
Average flight time2 hours 27 minutes
Popular airlineAmerican Airlines

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