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Cheap flight deals from Chicago to Portland Starting at $53

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

  • One way
  • Round-trip
      • Cheapest nonstop
        ORD11:10 am
        2h 32m
        Nonstop
        PWM02:42 pm
        Thu, Jan 16|Chicago - Portland|United Airlines
        $204$240
        15% OFF
        15% OFF
        $240$204

        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 $204 including taxes and charges.

      • ORD11:10 am
        2h 32m
        Nonstop
        PWM02:42 pm
        Thu, Feb 6|Chicago - Portland|United Airlines
        $204$240
        15% OFF
        15% OFF
        $240$204

        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 $204 including taxes and charges.

      • ORD10:59 am
        8h 13m
        1 stop
        PWM08:12 pm
        Mon, Feb 3|Chicago - Portland|Frontier Airlines
        $53$240
        78% OFF
        78% OFF
        $240$53

        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 $53 including taxes and charges.

      • MDW11:33 am
        7h 39m
        1 stop
        PWM08:12 pm
        Mon, Jan 27|Chicago - Portland|Frontier Airlines
        $55
        $55

        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 $55 including taxes and charges.

      • MDW11:33 am
        7h 39m
        1 stop
        PWM08:12 pm
        Mon, Jan 13|Chicago - Portland|Frontier Airlines
        $55
        $55

        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 $55 including taxes and charges.

      • ORD10:59 am
        8h 13m
        1 stop
        PWM08:12 pm
        Fri, Jan 10|Chicago - Portland|Frontier Airlines
        $61
        $61

        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 $61 including taxes and charges.

      • ORD10:59 am
        8h 13m
        1 stop
        PWM08:12 pm
        Fri, Jan 24|Chicago - Portland|Frontier Airlines
        $64
        $64

        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 $64 including taxes and charges.

      • ORD04:18 pm
        26h 54m
        1 stop
        PWM08:12 pm
        Sun, Jan 26|Chicago - Portland|Frontier Airlines
        $72
        $72

        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 $72 including taxes and charges.

      • MDW05:52 pm
        15h 31m
        1 stop
        PWM10:23 am
        Thu, Jan 2|Chicago - Portland|Frontier Airlines
        $79
        $79

        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 $79 including taxes and charges.

      • MDW06:49 pm
        23h 2m
        1 stop
        PWM06:51 pm
        Sat, Jan 4|Chicago - Portland|Frontier Airlines
        $80
        $80

        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 $80 including taxes and charges.

      • CHI01:00 pm
        3h 5m
        Nonstop
        PWM02:00 pm
        Thu, Jan 2|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.

When is the cheapest time to fly from Chicago to Portland?

Explore the best time to buy affordable tickets to Portland 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.

Find cheap airlines flights from Chicago to Portland

Compare prices from various providers below to understand which option best suits your travel needs, before enjoying a comfortable journey with a trusted airline from Chicago to Portland.

Frontier Airlines
From $53
American Airlines
From $90
Delta Air Lines
From $104
United Airlines
From $137
Southwest Airlines
From $184
Jetblue Airways
From $220
Spirit Airlines
From $717

Find more flights and airlines

Alternative Cheap Routes from Chicago to Portland

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

  • Cheapest
    Frontier Airlines
    ORD
    10:59 am
    8h 13m
    1 transfer
    PWM
    08:12 pm
    O'Hare International Airport - Portland International Jetport
    Mon, Feb 3Frontier Airlines
    $53
  • Frontier Airlines
    MDW
    11:33 am
    7h 39m
    1 transfer
    PWM
    08:12 pm
    Midway International Airport - Portland International Jetport
    Mon, Jan 27Frontier Airlines
    $55
  • Frontier Airlines
    MDW
    11:33 am
    7h 39m
    1 transfer
    PWM
    08:12 pm
    Midway International Airport - Portland International Jetport
    Mon, Jan 27Frontier Airlines
    $55
    Find More Flights

Frequently Asked Questions

  • 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 $323.

  • 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

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 Info | Chicago to Portland

Cheapest nonstop flight price$52
Cheapest round-trip ticket price$262
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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