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Flights from Portland to Chicago
Cheap flight deals from Portland to Chicago
We've found these cheap flights for you. You can book one-way or round-trip flight tickets.
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Round-trip
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One way
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Cheapest nonstopPDX 5:51 PM4h 5mNonstopORD 11:56 PMPortland - Chicago | Sat, May 24 | Hawaiian AirlinesORD 7:00 AM4h 23mNonstopPDX 9:23 AMChicago - Portland | Fri, May 30 | Hawaiian AirlinesPHP 9,566 PHP 11,83619% OFF19% OFFPHP 11,836 PHP 9,566
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PDX 5:51 PM4h 5mNonstopORD 11:56 PMPortland - Chicago | Sat, May 24 | Alaska AirlinesORD 7:00 AM4h 23mNonstopPDX 9:23 AMChicago - Portland | Fri, May 30 | Alaska AirlinesPHP 9,635 PHP 11,83619% OFF19% OFFPHP 11,836 PHP 9,635
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PDX 7:00 AM4h 8mNonstopORD 1:08 PMPortland - Chicago | Sun, May 25 | Alaska AirlinesORD 7:00 AM4h 23mNonstopPDX 9:23 AMChicago - Portland | Thu, May 29 | Alaska AirlinesPHP 9,666 PHP 11,83618% OFF18% OFFPHP 11,836 PHP 9,666
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PDX 5:51 PM4h 5mNonstopORD 11:56 PMPortland - Chicago | Wed, May 28 | Alaska AirlinesORD 7:00 AM4h 23mNonstopPDX 9:23 AMChicago - Portland | Sat, May 31 | Alaska AirlinesPHP 9,70518% OFFPHP 11,836 PHP 9,705
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PDX 5:51 PM4h 5mNonstopORD 11:56 PMPortland - Chicago | Thu, May 29 | Alaska AirlinesORD 7:00 AM4h 23mNonstopPDX 9:23 AMChicago - Portland | Sat, May 31 | Alaska AirlinesPHP 9,70518% OFFPHP 11,836 PHP 9,705
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PDX 2:33 PM18h 22m1 stopsORD 10:55 AMPortland - Chicago | Tue, May 6 | Spirit AirlinesORD 9:02 PM21h 43m1 stopsPDX 4:45 PMChicago - Portland | Tue, May 13 | Spirit AirlinesPHP 7,54836% OFFPHP 11,836 PHP 7,548
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PDX 9:21 PM29h 44m1 stopsORD 5:05 AMPortland - Chicago | Sat, Apr 19 | Frontier AirlinesORD 5:25 PM9h 17m1 stopsPDX 12:42 AMChicago - Portland | Fri, Apr 25 | Frontier AirlinesPHP 8,55728% OFFPHP 11,836 PHP 8,557
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PDX 5:40 PM9h 45m1 stopsORD 5:25 AMPortland - Chicago | Sun, May 11 | Spirit AirlinesORD 9:02 PM21h 43m1 stopsPDX 4:45 PMChicago - Portland | Tue, May 13 | Spirit AirlinesPHP 8,96024% OFFPHP 11,836 PHP 8,960
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PDX 5:40 PM15h 15m1 stopsORD 10:55 AMPortland - Chicago | Mon, May 12 | Spirit AirlinesORD 9:02 PM17h 38m1 stopsPDX 12:40 PMChicago - Portland | Tue, May 20 | Spirit AirlinesPHP 9,37221% OFFPHP 11,836 PHP 9,372
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PDX 7:01 PM9h 32m1 stopsORD 6:33 AMPortland - Chicago | Wed, Apr 23 | Spirit AirlinesORD 3:08 PM24h 29m1 stopsPDX 1:37 PMChicago - Portland | Mon, Apr 28 | Spirit AirlinesPHP 9,69718% OFFPHP 11,836 PHP 9,697
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PDX 1:00 PM17h 25m1 stopsCHI Invalid DatePortland - Chicago | Sun, Apr 20 | Normal AirlineCHI 3:00 PM6hNonstopPDX 4:00 PMChicago - Portland | Tue, Apr 22 | Normal AirlineFind More FlightsFind More Flights
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Cheapest nonstopPDX 5:51 PM4h 5mNonstopORD 11:56 PMPortland - Chicago | Sat, May 31 | Alaska AirlinesPHP 4,787 PHP 20,00076% OFF76% OFFPHP 20,000 PHP 4,787
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PDX 9:51 PM11h 32m1 stopsMDW 11:23 AMPortland - Chicago | Mon, May 5 | Frontier AirlinesPHP 3,584 PHP 20,00082% OFF82% OFFPHP 20,000 PHP 3,584
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PDX 5:16 PM28h 24m1 stopsORD 11:40 PMPortland - Chicago | Thu, Apr 24 | Frontier AirlinesPHP 3,615 PHP 20,00082% OFF82% OFFPHP 20,000 PHP 3,615
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PDX 5:40 PM15h 15m1 stopsORD 10:55 AMPortland - Chicago | Mon, May 12 | Spirit AirlinesPHP 4,67077% OFFPHP 20,000 PHP 4,670
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PDX 7:01 PM13h 54m1 stopsORD 10:55 AMPortland - Chicago | Tue, May 6 | Spirit AirlinesPHP 4,67877% OFFPHP 20,000 PHP 4,678
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PDX 5:40 PM9h 45m1 stopsORD 5:25 AMPortland - Chicago | Tue, May 13 | Spirit AirlinesPHP 4,69477% OFFPHP 20,000 PHP 4,694
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PDX 1:15 PM23h 33m1 stopsMDW 2:48 PMPortland - Chicago | Thu, May 1 | Frontier AirlinesPHP 4,70176% OFFPHP 20,000 PHP 4,701
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PDX 9:38 PM11h 43m1 stopsMDW 11:21 AMPortland - Chicago | Fri, Apr 25 | Frontier AirlinesPHP 6,23069% OFFPHP 20,000 PHP 6,230
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PDX 10:00 AM11h 59m1 stopsORD 11:59 PMPortland - Chicago | Sat, Apr 19 | Frontier AirlinesPHP 11,60642% OFFPHP 20,000 PHP 11,606
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PDX 2:32 PM14h 1m1 stopsORD 6:33 AMPortland - Chicago | Sun, Apr 20 | Spirit AirlinesPHP 16,40018% OFFPHP 20,000 PHP 16,400
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PDX 1:00 PM17h 25m1 stopsCHI Invalid DatePortland - Chicago | Sun, Apr 20 | Normal AirlineFind More FlightsFind More Flights
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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 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.
Frequently Asked Questions
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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 PHP 19,689. -
How long does it take to fly from Portland (PDX) to Chicago (CHI) and what is the distance?
It takes around 5 hours 33 minutes to fly from Portland (PDX) to Chicago (CHI). -
What are the most popular airlines that fly from Portland (PDX) to Chicago (CHI)?
Airlines with flights from Portland (PDX) to Chicago (CHI): Brussels Airlines, Alaska Airlines, American Airlines, United Airlines, Lufthansa, Air Canada, Gulf Air and Iberia.
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.
Book Early
Once prices are gone, they're gone. Lock in deals while you can!
Compare Flight Prices
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Look Out for Deals
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Check One-way Fares
Buying two cheap one-way flights can sometimes be a better deal than a round-trip.
Try Different Dates
Flying during the week, early in the morning, or late at night can help save money.
Use the Trip.com App
Save up to £10 per person when booking your flights on Trip.com
Flight Info | Portland to Chicago
Cheapest one-way flight price | PHP 3,584 |
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Cheapest round-trip ticket price | PHP 9,565 |
Off-season for travel | March |
Peak season for travel | June |
Flight distance | 2,816.22 km |
Average flight time | 5 hours 33 minutes |
Popular airline | Alaska Airlines |
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