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Flights from Chicago to Portland
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Flights from Chicago to Portland Starting at NZD 92

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

  • One way
  • Round-trip
      • Cheapest nonstop
        MDW08:30
        4h 25m
        Nonstop
        PDX10:55
        Tue, Jan 14|Chicago - Portland|Southwest Airlines
        NZD 114NZD 165
        31% OFF
        31% OFF
        NZD 165NZD 114

        Choose Southwest Airlines flights from Chicago to Portland. The one-way direct flight with Southwest Airlines departs from Midway International Airport on Tue, Jan 14, arriving at Portland International Airport. One-way Prices start from NZD 114 including taxes and charges.

      • ORD18:55
        4h 46m
        Nonstop
        PDX21:41
        Wed, Jan 8|Chicago - Portland|Alaska Airlines
        NZD 144NZD 165
        13% OFF
        13% OFF
        NZD 165NZD 144

        Choose Alaska Airlines flights from Chicago to Portland. The one-way direct flight with Alaska Airlines departs from O'Hare International Airport on Wed, Jan 8, arriving at Portland International Airport. One-way Prices start from NZD 144 including taxes and charges.

      • MDW07:15
        29h 46m
        1 stop
        PDX11:01
        Thu, Jan 23|Chicago - Portland|Frontier Airlines
        NZD 92NZD 165
        45% OFF
        45% OFF
        NZD 165NZD 92

        Choose Frontier Airlines flights from Chicago to Portland. The one-way connecting flight with Frontier Airlines departs from Midway International Airport on Thu, Jan 23, arriving at Portland International Airport. One-way Prices start from NZD 92 including taxes and charges.

      • ORD18:32
        8h 5m
        1 stop
        PDX00:37
        Sat, Feb 15|Chicago - Portland|Frontier Airlines
        NZD 95
        NZD 95

        Choose Frontier Airlines flights from Chicago to Portland. The one-way connecting flight with Frontier Airlines departs from O'Hare International Airport on Sat, Feb 15, arriving at Portland International Airport. One-way Prices start from NZD 95 including taxes and charges.

      • ORD18:32
        8h 5m
        1 stop
        PDX00:37
        Sat, Mar 1|Chicago - Portland|Frontier Airlines
        NZD 96
        NZD 96

        Choose Frontier Airlines flights from Chicago to Portland. The one-way connecting flight with Frontier Airlines departs from O'Hare International Airport on Sat, Mar 1, arriving at Portland International Airport. One-way Prices start from NZD 96 including taxes and charges.

      • MDW08:15
        17h 52m
        1 stop
        PDX00:07
        Tue, Jan 21|Chicago - Portland|Frontier Airlines
        NZD 101
        NZD 101

        Choose Frontier Airlines flights from Chicago to Portland. The one-way connecting flight with Frontier Airlines departs from Midway International Airport on Tue, Jan 21, arriving at Portland International Airport. One-way Prices start from NZD 101 including taxes and charges.

      • ORD18:36
        17h 9m
        1 stop
        PDX09:45
        Thu, Jan 30|Chicago - Portland|Frontier Airlines
        NZD 101
        NZD 101

        Choose Frontier Airlines flights from Chicago to Portland. The one-way connecting flight with Frontier Airlines departs from O'Hare International Airport on Thu, Jan 30, arriving at Portland International Airport. One-way Prices start from NZD 101 including taxes and charges.

      • MDW08:15
        18h
        1 stop
        PDX00:15
        Wed, Jan 15|Chicago - Portland|Frontier Airlines
        NZD 103
        NZD 103

        Choose Frontier Airlines flights from Chicago to Portland. The one-way connecting flight with Frontier Airlines departs from Midway International Airport on Wed, Jan 15, arriving at Portland International Airport. One-way Prices start from NZD 103 including taxes and charges.

      • MDW07:05
        19h 32m
        1 stop
        PDX00:37
        Tue, Feb 18|Chicago - Portland|Frontier Airlines
        NZD 104
        NZD 104

        Choose Frontier Airlines flights from Chicago to Portland. The one-way connecting flight with Frontier Airlines departs from Midway International Airport on Tue, Feb 18, arriving at Portland International Airport. One-way Prices start from NZD 104 including taxes and charges.

      • MDW08:15
        18h
        1 stop
        PDX00:15
        Wed, Jan 8|Chicago - Portland|Frontier Airlines
        NZD 104
        NZD 104

        Choose Frontier Airlines flights from Chicago to Portland. The one-way connecting flight with Frontier Airlines departs from Midway International Airport on Wed, Jan 8, arriving at Portland International Airport. One-way Prices start from NZD 104 including taxes and charges.

      • CHI01:00 pm
        3h 5m
        Nonstop
        PDX02:00 pm
        Sat, Jan 11|Chicago - Portland|Southwest 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

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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 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 92
Southwest Airlines
From NZD 114
Alaska Airlines
From NZD 144
Delta Air Lines
From NZD 156
American Airlines
From NZD 200
United Airlines
From NZD 223
Allegiant Air
From NZD 240
Spirit Airlines
From NZD 291

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
    MDW
    07:15
    29h 46m
    1 transfer
    PDX
    11:01
    Midway International Airport - Portland International Airport
    Thu, Jan 23Frontier Airlines
    NZD 92
  • Frontier Airlines
    ORD
    18:32
    8h 5m
    1 transfer
    PDX
    00:37
    O'Hare International Airport - Portland International Airport
    Sat, Feb 15Frontier Airlines
    NZD 95
  • Allegiant Air
    RFD
    12:44
    23h 3m
    1 transfer
    PDX
    09:47
    Chicago Rockford International Airport - Portland International Airport
    Sun, Jan 12Allegiant Air
    NZD 240
  • Allegiant Air
    RFD
    12:44
    23h 3m
    1 transfer
    PDX
    09:47
    Chicago Rockford International Airport - Portland International Airport
    Sun, Jan 12Allegiant Air
    NZD 240
    Find More Flights

FAQ

  • When are flight tickets from Chicago (CHI) to Portland (PDX) 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 (PDX) cost?

    According to Trip.com's data, the lowest price is around NZD 462.

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

    It takes around 4 hours 49 minutes to fly from Chicago (CHI) to Portland (PDX).

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

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 91
Cheapest round-trip ticket priceNZD 270
Off-season for travelDecember
Peak season for travelApril
Flight distance2,816.22 km
Average flight time4 hours 49 minutes
Popular airlineAlaska Airlines

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