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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 | Sun, May 25 | Alaska AirlinesORD 7:00 AM4h 23mNonstopPDX 9:23 AMChicago - Portland | Thu, May 29 | Alaska AirlinesPHP 9,806 PHP 14,10130% OFF30% OFFPHP 14,101 PHP 9,806
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PDX 5:51 PM4h 5mNonstopORD 11:56 PMPortland - Chicago | Sat, May 24 | Hawaiian AirlinesORD 7:00 AM4h 23mNonstopPDX 9:23 AMChicago - Portland | Sat, May 31 | Hawaiian AirlinesPHP 10,012 PHP 14,10128% OFF28% OFFPHP 14,101 PHP 10,012
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PDX 6:40 AM15h 41m1 stopsMDW 12:21 AMPortland - Chicago | Mon, Apr 7 | Frontier AirlinesMDW 6:45 AM19h 52m1 stopsPDX 12:37 AMChicago - Portland | Tue, Apr 15 | Frontier AirlinesPHP 7,136 PHP 14,10149% OFF49% OFFPHP 14,101 PHP 7,136
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PDX 9:54 AM12h 27m1 stopsMDW 12:21 AMPortland - Chicago | Tue, Apr 1 | Frontier AirlinesMDW 6:45 AM19h 52m1 stopsPDX 12:37 AMChicago - Portland | Wed, Apr 9 | Frontier AirlinesPHP 7,16749% OFFPHP 14,101 PHP 7,167
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PDX 6:40 AM15h 41m1 stopsMDW 12:21 AMPortland - Chicago | Thu, Apr 10 | Frontier AirlinesMDW 8:50 PM13h 57m1 stopsPDX 8:47 AMChicago - Portland | Thu, Apr 17 | Frontier AirlinesPHP 7,29448% OFFPHP 14,101 PHP 7,294
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PDX 3:22 PM7h 41m1 stopsORD 1:03 AMPortland - Chicago | Wed, Apr 16 | Frontier AirlinesORD 6:45 AM19h 38m1 stopsPDX 12:23 AMChicago - Portland | Sat, Apr 19 | Frontier AirlinesPHP 7,59446% OFFPHP 14,101 PHP 7,594
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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 7,68945% OFFPHP 14,101 PHP 7,689
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PDX 3:22 PM7h 41m1 stopsORD 1:03 AMPortland - Chicago | Wed, Apr 9 | Frontier AirlinesORD 6:45 AM19h 52m1 stopsPDX 12:37 AMChicago - Portland | Sun, Apr 13 | Frontier AirlinesPHP 7,88644% OFFPHP 14,101 PHP 7,886
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PDX 9:01 AM9h 13m1 stopsMDW 8:14 PMPortland - Chicago | Mon, Apr 14 | Frontier AirlinesMDW 6:45 AM19h 52m1 stopsPDX 12:37 AMChicago - Portland | Tue, Apr 15 | Frontier AirlinesPHP 7,93444% OFFPHP 14,101 PHP 7,934
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PDX 9:54 AM12h 21m1 stopsORD 12:15 AMPortland - Chicago | Tue, Apr 8 | Frontier AirlinesMDW 6:21 AM20h 2m1 stopsPDX 12:23 AMChicago - Portland | Sat, Apr 12 | Frontier AirlinesPHP 8,32141% OFFPHP 14,101 PHP 8,321
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PDX 10:00 AM11h 59m1 stopsORD 11:59 PMPortland - Chicago | Sat, Apr 12 | Frontier AirlinesORD 7:39 PM15h 8m1 stopsPDX 8:47 AMChicago - Portland | Sun, Apr 13 | Frontier AirlinesPHP 8,61339% OFFPHP 14,101 PHP 8,613
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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 8,71638% OFFPHP 14,101 PHP 8,716
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PDX 1:00 PM17h 25m1 stopsCHI Invalid DatePortland - Chicago | Tue, Apr 1 | Normal AirlineCHI 3:00 PM6hNonstopPDX 4:00 PMChicago - Portland | Thu, Apr 3 | Normal AirlineFind More FlightsFind More Flights
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Cheapest nonstopPDX 5:51 PM4h 5mNonstopORD 11:56 PMPortland - Chicago | Sat, May 24 | Alaska AirlinesPHP 4,876 PHP 7,01230% OFF30% OFFPHP 7,012 PHP 4,876
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PDX 5:51 PM4h 5mNonstopORD 11:56 PMPortland - Chicago | Sat, May 24 | Hawaiian AirlinesPHP 4,978 PHP 7,01228% OFF28% OFFPHP 7,012 PHP 4,978
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PDX 9:01 AM9h 13m1 stopsMDW 8:14 PMPortland - Chicago | Mon, Apr 7 | Frontier AirlinesPHP 2,734 PHP 7,01261% OFF61% OFFPHP 7,012 PHP 2,734
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PDX 10:04 AM12h 38m1 stopsORD 12:42 AMPortland - Chicago | Wed, Apr 16 | Frontier AirlinesPHP 3,24854% OFFPHP 7,012 PHP 3,248
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PDX 3:22 PM7h 41m1 stopsORD 1:03 AMPortland - Chicago | Wed, Apr 9 | Frontier AirlinesPHP 3,34352% OFFPHP 7,012 PHP 3,343
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PDX 9:54 AM12h 21m1 stopsORD 12:15 AMPortland - Chicago | Tue, Apr 8 | Frontier AirlinesPHP 3,42951% OFFPHP 7,012 PHP 3,429
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PDX 6:40 AM15h 35m1 stopsORD 12:15 AMPortland - Chicago | Thu, Apr 17 | Frontier AirlinesPHP 3,58849% OFFPHP 7,012 PHP 3,588
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PDX 9:51 PM11h 32m1 stopsMDW 11:23 AMPortland - Chicago | Mon, May 5 | Frontier AirlinesPHP 3,65148% OFFPHP 7,012 PHP 3,651
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PDX 10:16 AM12h 47m1 stopsORD 1:03 AMPortland - Chicago | Thu, Apr 3 | Frontier AirlinesPHP 3,66748% OFFPHP 7,012 PHP 3,667
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PDX 5:16 PM28h 24m1 stopsORD 11:40 PMPortland - Chicago | Thu, Apr 24 | Frontier AirlinesPHP 3,68247% OFFPHP 7,012 PHP 3,682
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PDX 7:01 PM9h 32m1 stopsORD 6:33 AMPortland - Chicago | Wed, Apr 16 | Spirit AirlinesPHP 4,01443% OFFPHP 7,012 PHP 4,014
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PDX 9:21 PM29h 44m1 stopsORD 5:05 AMPortland - Chicago | Sat, Apr 5 | Frontier AirlinesPHP 4,15641% OFFPHP 7,012 PHP 4,156
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PDX 1:00 PM17h 25m1 stopsCHI Invalid DatePortland - Chicago | Tue, Apr 1 | 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 20,055. -
How long does it take to fly from Portland (PDX) to Chicago (CHI) and what is the distance?
It takes around 5 hours 16 minutes to fly from Portland (PDX) to Chicago (CHI). -
What is the transportation method from the main airport to downtown in Chicago?
- The distance from O'Hare International Airport to downtown is about 25 km. It takes about 40 minutes by taxi.
- The distance from Midway International Airport to downtown is about 14 km. It takes about 30 minutes by taxi.
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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, Southwest Airlines, 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.
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Check One-way Fares
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Flight Info | Portland to Chicago
Cheapest one-way flight price | PHP 2,734 |
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Cheapest round-trip ticket price | PHP 8,866 |
Off-season for travel | March |
Peak season for travel | December |
Flight distance | 2,816.22 km |
Average flight time | 5 hours 16 minutes |
Popular airline | Alaska Airlines |
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