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Flights from Portland to Chicago
Cheap flight deals from Portland to Chicago Starting at PHP 4,640
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 nonstopPWM 6:00 AM2h 52mNonstopORD 7:52 AMPortland - Chicago | Mon, Apr 14 | United AirlinesORD 6:12 PM2h 23mNonstopPWM 9:35 PMChicago - Portland | Wed, Apr 16 | United AirlinesPHP 13,826 PHP 18,67026% OFF26% OFFPHP 18,670 PHP 13,826
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PWM 6:13 AM2h 52mNonstopORD 8:05 AMPortland - Chicago | Sat, May 3 | United AirlinesORD 5:53 PM2h 23mNonstopPWM 9:16 PMChicago - Portland | Tue, May 6 | United AirlinesPHP 15,123 PHP 18,67019% OFF19% OFFPHP 18,670 PHP 15,123
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PWM 7:22 PM14h 5m1 stopsORD 8:27 AMPortland - Chicago | Mon, Apr 14 | Frontier AirlinesORD 11:45 AM20h 27m1 stopsPWM 9:12 AMChicago - Portland | Wed, Apr 16 | Frontier AirlinesPHP 10,348 PHP 18,67045% OFF45% OFFPHP 18,670 PHP 10,348
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PWM 10:17 AM10h 38m1 stopsORD 7:55 PMPortland - Chicago | Thu, Apr 10 | Frontier AirlinesORD 9:25 AM22h 47m1 stopsPWM 9:12 AMChicago - Portland | Sat, Apr 12 | Frontier AirlinesPHP 10,90942% OFFPHP 18,670 PHP 10,909
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PWM 7:22 PM29h 24m1 stopsORD 11:46 PMPortland - Chicago | Fri, Apr 11 | Frontier AirlinesORD 11:25 AM25h 45m1 stopsPWM 2:10 PMChicago - Portland | Sun, Apr 13 | Frontier AirlinesPHP 11,54238% OFFPHP 18,670 PHP 11,542
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PWM 8:23 PM28h 9m1 stopsORD 11:32 PMPortland - Chicago | Sun, May 4 | Frontier AirlinesORD 4:15 PM27h 25m1 stopsPWM 8:40 PMChicago - Portland | Thu, May 8 | Frontier AirlinesPHP 11,57338% OFFPHP 18,670 PHP 11,573
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PWM 5:20 AM7h 43m1 stopsMDW 12:03 PMPortland - Chicago | Wed, Apr 30 | Delta Air LinesMDW 7:00 AM5h 50m1 stopsPWM 1:50 PMChicago - Portland | Wed, May 7 | Delta Air LinesPHP 11,73937% OFFPHP 18,670 PHP 11,739
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PWM 5:25 AM6h 13m1 stopsORD 10:38 AMPortland - Chicago | Thu, Apr 3 | American AirlinesORD 11:45 AM20h 42m1 stopsPWM 9:27 AMChicago - Portland | Wed, Apr 9 | Frontier AirlinesPHP 11,79437% OFFPHP 18,670 PHP 11,794
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PWM 3:08 PM7h 53m1 stopsORD 10:01 PMPortland - Chicago | Thu, Apr 3 | Delta Air LinesORD 6:45 AM4h 24m1 stopsPWM 12:09 PMChicago - Portland | Sun, Apr 6 | Delta Air LinesPHP 11,82637% OFFPHP 18,670 PHP 11,826
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PWM 5:32 AM5h 23m1 stopsORD 9:55 AMPortland - Chicago | Mon, Apr 14 | Delta Air LinesORD 6:00 AM6h 12m1 stopsPWM 1:12 PMChicago - Portland | Thu, Apr 17 | Delta Air LinesPHP 11,92136% OFFPHP 18,670 PHP 11,921
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PWM 12:25 PM7h 20m1 stopsORD 6:45 PMPortland - Chicago | Tue, Apr 1 | Delta Air LinesORD 2:50 PM7h 5m1 stopsPWM 10:55 PMChicago - Portland | Tue, Apr 8 | Delta Air LinesPHP 11,93736% OFFPHP 18,670 PHP 11,937
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PWM 7:00 AM6h 41m1 stopsORD 12:41 PMPortland - Chicago | Sat, Mar 29 | Delta Air LinesORD 5:30 PM5h 29m1 stopsPWM 11:59 PMChicago - Portland | Fri, Apr 4 | Delta Air LinesPHP 11,96036% OFFPHP 18,670 PHP 11,960
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PWM 1:00 PM17h 25m1 stopsCHI Invalid DatePortland - Chicago | Tue, Mar 25 | Normal AirlineCHI 3:00 PM6hNonstopPWM 4:00 PMChicago - Portland | Thu, Mar 27 | Normal AirlineFind More FlightsFind More Flights
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Cheapest nonstopPWM 6:00 AM2h 52mNonstopORD 7:52 AMPortland - Chicago | Wed, Apr 23 | United AirlinesPHP 7,130 PHP 8,83219% OFF19% OFFPHP 8,832 PHP 7,130
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PWM 6:13 AM2h 52mNonstopORD 8:05 AMPortland - Chicago | Tue, May 20 | United AirlinesPHP 7,154 PHP 8,83219% OFF19% OFFPHP 8,832 PHP 7,154
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PWM 7:29 PM20h 37m1 stopsORD 3:06 PMPortland - Chicago | Wed, Apr 16 | Frontier AirlinesPHP 4,640 PHP 8,83247% OFF47% OFFPHP 8,832 PHP 4,640
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PWM 3:05 PM20h 35m1 stopsORD 10:40 AMPortland - Chicago | Tue, Apr 15 | Frontier AirlinesPHP 4,90145% OFFPHP 8,832 PHP 4,901
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PWM 7:22 PM14h 5m1 stopsORD 8:27 AMPortland - Chicago | Mon, Apr 7 | Frontier AirlinesPHP 4,94144% OFFPHP 8,832 PHP 4,941
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PWM 8:01 PM28h 35m1 stopsORD 11:36 PMPortland - Chicago | Thu, Apr 24 | Frontier AirlinesPHP 5,18641% OFFPHP 8,832 PHP 5,186
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PWM 8:35 PM15h 22m1 stopsORD 10:57 AMPortland - Chicago | Mon, Mar 24 | Frontier AirlinesPHP 5,49438% OFFPHP 8,832 PHP 5,494
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PWM 6:10 AM7h 17m1 stopsORD 12:27 PMPortland - Chicago | Thu, Apr 24 | Jetblue AirwaysPHP 5,56537% OFFPHP 8,832 PHP 5,565
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PWM 8:01 PM28h 35m1 stopsORD 11:36 PMPortland - Chicago | Sun, Apr 27 | Frontier AirlinesPHP 5,77935% OFFPHP 8,832 PHP 5,779
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PWM 8:23 PM28h 9m1 stopsORD 11:32 PMPortland - Chicago | Sun, May 4 | Frontier AirlinesPHP 5,77935% OFFPHP 8,832 PHP 5,779
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PWM 7:00 AM6h 39m1 stopsORD 12:39 PMPortland - Chicago | Tue, Apr 22 | Delta Air LinesPHP 5,92933% OFFPHP 8,832 PHP 5,929
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PWM 5:20 AM7h 43m1 stopsMDW 12:03 PMPortland - Chicago | Tue, Apr 15 | Delta Air LinesPHP 6,08731% OFFPHP 8,832 PHP 6,087
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PWM 1:00 PM17h 25m1 stopsCHI Invalid DatePortland - Chicago | Tue, Mar 25 | 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 (PWM) 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 (PWM) to Chicago (CHI) cost?
According to Trip.com's data, the lowest price is around PHP 21,454. -
How long does it take to fly from Portland (PWM) to Chicago (CHI) and what is the distance?
It takes around 4 hours 42 minutes to fly from Portland (PWM) 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 (PWM) to Chicago (CHI)?
Airlines with flights from Portland (PWM) to Chicago (CHI): United Airlines, Emirates and Air New Zealand.
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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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.
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Save up to £10 per person when booking your flights on Trip.com
Flight Info | Portland to Chicago
Cheapest one-way flight price | PHP 4,640 |
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Cheapest round-trip ticket price | PHP 13,786 |
Off-season for travel | March |
Peak season for travel | June |
Flight distance | 1,425.81 km |
Average flight time | 4 hours 42 minutes |
Popular airline | Jetblue Airways |
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