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Flights from Chicago to Portland
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Book flight tickets from Chicago to Portland starting at ₹ 4,407

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
        MDW08:30
        4h 25m
        Nonstop
        PDX10:55
        Tue, Jan 14|Chicago - Portland|Southwest Airlines
        ₹ 5,486₹ 7,962
        31% OFF
        31% OFF
        ₹ 7,962₹ 5,486

        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 ticket prices start from ₹ 5,486 including taxes and charges.

      • ORD18:55
        4h 46m
        Nonstop
        PDX21:41
        Wed, Jan 8|Chicago - Portland|Alaska Airlines
        ₹ 6,927₹ 7,962
        13% OFF
        13% OFF
        ₹ 7,962₹ 6,927

        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 ticket prices start from ₹ 6,927 including taxes and charges.

      • MDW07:15
        29h 46m
        1 stop
        PDX11:01
        Thu, Jan 23|Chicago - Portland|Frontier Airlines
        ₹ 4,407₹ 7,962
        45% OFF
        45% OFF
        ₹ 7,962₹ 4,407

        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 ticket prices start from ₹ 4,407 including taxes and charges.

      • ORD18:32
        8h 5m
        1 stop
        PDX00:37
        Sat, Feb 15|Chicago - Portland|Frontier Airlines
        ₹ 4,595
        ₹ 4,595

        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 ticket prices start from ₹ 4,595 including taxes and charges.

      • ORD18:32
        8h 5m
        1 stop
        PDX00:37
        Sat, Mar 1|Chicago - Portland|Frontier Airlines
        ₹ 4,618
        ₹ 4,618

        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 ticket prices start from ₹ 4,618 including taxes and charges.

      • MDW08:15
        17h 52m
        1 stop
        PDX00:07
        Tue, Jan 21|Chicago - Portland|Frontier Airlines
        ₹ 4,864
        ₹ 4,864

        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 ticket prices start from ₹ 4,864 including taxes and charges.

      • ORD18:36
        17h 9m
        1 stop
        PDX09:45
        Thu, Jan 30|Chicago - Portland|Frontier Airlines
        ₹ 4,876
        ₹ 4,876

        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 ticket prices start from ₹ 4,876 including taxes and charges.

      • MDW08:15
        18h
        1 stop
        PDX00:15
        Wed, Jan 15|Chicago - Portland|Frontier Airlines
        ₹ 4,970
        ₹ 4,970

        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 ticket prices start from ₹ 4,970 including taxes and charges.

      • MDW07:05
        19h 32m
        1 stop
        PDX00:37
        Tue, Feb 18|Chicago - Portland|Frontier Airlines
        ₹ 4,993
        ₹ 4,993

        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 ticket prices start from ₹ 4,993 including taxes and charges.

      • MDW08:15
        18h
        1 stop
        PDX00:15
        Wed, Jan 8|Chicago - Portland|Frontier Airlines
        ₹ 5,028
        ₹ 5,028

        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 ticket prices start from ₹ 5,028 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

These price trend charts carefully monitor and predict how flight prices from Chicago to Portland will change. Keep a close eye on them to understand when the best time to buy your tickets is.

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

Airlines Flying from Chicago to Portland

We have a range of prices from different airlines providing flights from Chicago to Portland. Check below for the journey which best suits your travel needs.

Frontier Airlines
From ₹ 4,407
Southwest Airlines
From ₹ 5,486
Alaska Airlines
From ₹ 6,927
Delta Air Lines
From ₹ 7,525
American Airlines
From ₹ 9,635
United Airlines
From ₹ 10,760
Allegiant Air
From ₹ 11,557
Spirit Airlines
From ₹ 14,030

Find more flights and airlines

Alternative 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
    MDW
    07:15
    29h 46m
    1 transfer
    PDX
    11:01
    Midway International Airport - Portland International Airport
    Thu, Jan 23Frontier Airlines
    ₹ 4,407
  • Frontier Airlines
    ORD
    18:32
    8h 5m
    1 transfer
    PDX
    00:37
    O'Hare International Airport - Portland International Airport
    Sat, Feb 15Frontier Airlines
    ₹ 4,595
  • Allegiant Air
    RFD
    12:44
    23h 3m
    1 transfer
    PDX
    09:47
    Chicago Rockford International Airport - Portland International Airport
    Sun, Jan 12Allegiant Air
    ₹ 11,557
  • Allegiant Air
    RFD
    12:44
    23h 3m
    1 transfer
    PDX
    09:47
    Chicago Rockford International Airport - Portland International Airport
    Sun, Jan 12Allegiant Air
    ₹ 11,557
    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 ₹ 22,270.

  • 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

If you leave it until the last minute and forget to check some of the key information when booking tickets, prices can often end up skyrocketing. Below, you can find our top tips for getting the best value flights – from changing dates to chasing deals, there are plenty ways to keep your next trip affordable.
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 price₹ 4,407
Cheapest round-trip ticket price₹ 13,045
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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