AED 297 Cheap Flights from Portland to Chicago
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Flights from Portland to Chicago
Cheap flight deals from Portland to Chicago Starting at AED 297
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 nonstop
PWM 06:002h 52mNonstopORD 07:52Portland - Chicago | Mon, Apr 14 | United Airlines
ORD 18:122h 23mNonstopPWM 21:35Chicago - Portland | Wed, Apr 16 | United AirlinesAED 886 AED 1,00312% OFF12% OFFAED 1,003 AED 886 -
PWM 06:132h 52mNonstopORD 08:05Portland - Chicago | Sat, May 3 | United Airlines
ORD 08:002h 32mNonstopPWM 11:32Chicago - Portland | Tue, May 6 | American AirlinesAED 913 AED 1,0039% OFF9% OFFAED 1,003 AED 913
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PWM 19:2214h 5m1 stopsORD 08:27Portland - Chicago | Mon, Apr 14 | Frontier Airlines
ORD 11:4520h 27m1 stopsPWM 09:12Chicago - Portland | Wed, Apr 16 | Frontier AirlinesAED 663 AED 1,00334% OFF34% OFFAED 1,003 AED 663 -
PWM 10:1710h 38m1 stopsORD 19:55Portland - Chicago | Thu, Apr 10 | Frontier Airlines
ORD 09:2522h 47m1 stopsPWM 09:12Chicago - Portland | Sat, Apr 12 | Frontier AirlinesAED 69930% OFFAED 1,003 AED 699
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PWM 19:2229h 24m1 stopsORD 23:46Portland - Chicago | Fri, Apr 11 | Frontier Airlines
ORD 11:2525h 45m1 stopsPWM 14:10Chicago - Portland | Sun, Apr 13 | Frontier AirlinesAED 73926% OFFAED 1,003 AED 739
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PWM 20:2328h 9m1 stopsORD 23:32Portland - Chicago | Sun, May 4 | Frontier Airlines
ORD 16:1527h 25m1 stopsPWM 20:40Chicago - Portland | Thu, May 8 | Frontier AirlinesAED 74226% OFFAED 1,003 AED 742
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PWM 05:207h 43m1 stopsMDW 12:03Portland - Chicago | Wed, Apr 30 | Delta Air Lines
MDW 07:005h 50m1 stopsPWM 13:50Chicago - Portland | Wed, May 7 | Delta Air LinesAED 75225% OFFAED 1,003 AED 752 -
PWM 05:256h 13m1 stopsORD 10:38Portland - Chicago | Thu, Apr 3 | American Airlines
ORD 11:4520h 42m1 stopsPWM 09:27Chicago - Portland | Wed, Apr 9 | Frontier AirlinesAED 75625% OFFAED 1,003 AED 756 -
PWM 15:087h 53m1 stopsORD 22:01Portland - Chicago | Thu, Apr 3 | Delta Air Lines
ORD 06:454h 24m1 stopsPWM 12:09Chicago - Portland | Sun, Apr 6 | Delta Air LinesAED 75824% OFFAED 1,003 AED 758
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PWM 05:325h 23m1 stopsORD 09:55Portland - Chicago | Mon, Apr 14 | Delta Air Lines
ORD 06:006h 12m1 stopsPWM 13:12Chicago - Portland | Thu, Apr 17 | Delta Air LinesAED 76424% OFFAED 1,003 AED 764
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PWM 12:257h 20m1 stopsORD 18:45Portland - Chicago | Tue, Apr 1 | Delta Air Lines
ORD 14:507h 5m1 stopsPWM 22:55Chicago - Portland | Tue, Apr 8 | Delta Air LinesAED 76524% OFFAED 1,003 AED 765
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PWM 07:006h 41m1 stopsORD 12:41Portland - Chicago | Sat, Mar 29 | Delta Air Lines
ORD 17:305h 29m1 stopsPWM 23:59Chicago - Portland | Fri, Apr 4 | Delta Air LinesAED 76624% OFFAED 1,003 AED 766
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PWM 13:0017h 25m1 stopsCHI Invalid DatePortland - Chicago | Mon, Mar 24 | Normal Airline
CHI 15:006hNonstopPWM 16:00Chicago - Portland | Wed, Mar 26 | Normal AirlineFind More FlightsFind More Flights
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Cheapest nonstop
PWM 06:002h 52mNonstopORD 07:52Portland - Chicago | Wed, Apr 23 | United AirlinesAED 457 AED 53915% OFF15% OFFAED 539 AED 457
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PWM 06:002h 52mNonstopORD 07:52Portland - Chicago | Mon, Apr 7 | United AirlinesAED 490 AED 5399% OFF9% OFFAED 539 AED 490
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PWM 19:2920h 37m1 stopsORD 15:06Portland - Chicago | Wed, Apr 16 | Frontier AirlinesAED 297 AED 53945% OFF45% OFFAED 539 AED 297
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PWM 15:0520h 35m1 stopsORD 10:40Portland - Chicago | Tue, Apr 15 | Frontier AirlinesAED 31442% OFFAED 539 AED 314
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PWM 19:2214h 5m1 stopsORD 08:27Portland - Chicago | Mon, Apr 7 | Frontier AirlinesAED 31741% OFFAED 539 AED 317
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PWM 20:0128h 35m1 stopsORD 23:36Portland - Chicago | Thu, Apr 24 | Frontier AirlinesAED 33238% OFFAED 539 AED 332
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PWM 20:3515h 22m1 stopsORD 10:57Portland - Chicago | Mon, Mar 24 | Frontier AirlinesAED 35235% OFFAED 539 AED 352
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PWM 06:107h 17m1 stopsORD 12:27Portland - Chicago | Thu, Apr 24 | Jetblue AirwaysAED 35734% OFFAED 539 AED 357 -
PWM 20:0128h 35m1 stopsORD 23:36Portland - Chicago | Sun, Apr 27 | Frontier AirlinesAED 37031% OFFAED 539 AED 370
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PWM 20:2328h 9m1 stopsORD 23:32Portland - Chicago | Sun, May 4 | Frontier AirlinesAED 37031% OFFAED 539 AED 370
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PWM 07:006h 35m1 stopsMDW 12:35Portland - Chicago | Tue, Apr 22 | Delta Air LinesAED 38028% OFFAED 539 AED 380
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PWM 05:207h 43m1 stopsMDW 12:03Portland - Chicago | Tue, Apr 15 | Delta Air LinesAED 39028% OFFAED 539 AED 390
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PWM 13:0017h 25m1 stopsCHI Invalid DatePortland - Chicago | Mon, Mar 24 | 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.
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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 date and time of your booking. By analyzing data from all airlines, 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 AED 1,374. -
How long does it take to fly from Portland (PWM) to Chicago (CHI)?
It takes about 5 hours 4 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, by taxi about 40 minutes.
- The distance from Midway International Airport to downtown is about 14 km, by taxi about 30 minutes.
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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. -
What's the most popular airline for non-stop flights from Portland (PWM) to Chicago (CHI)?
United Airlines operates 2 non-stop flights from Portland (PWM) to Chicago (CHI). -
How many airports are there in Chicago (CHI)?
There are 3 airport(s) near Chicago (CHI): Midway International Airport, O'Hare International Airport and Chicago Rockford International Airport.
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.
Being flexible with your dates to get the cheapest Portland to Chicago ticket.
Tap "Date" on flight search bar to scan through the calender for Portland to Chicago airfare over next 6 months in 2025. If you would like to fly in next 3 months, it seems the cheapest date is on Wed, Apr 23 at AED 457 for one-way flights.
Compare cheap Portland to Chicago flight deals from over hundreds of airlines.
Our extensive search allows you to compare prices from over 500 airlines to choose the cheapest flight tickets from Portland to Chicago. The cheapest airline operating is United Airlines.
Set up a Price Alert
By setting up a Price Alert for your Portland to Chicago route, you can easily track the price of your airline tickets from without manually checking every day.
Don't miss cheap Portland to Chicago flight deals and promo codes.
You can always get the latest deals through Trip.com Deals and Promo Codes for cheap flights. If registering a free membership, you can receive more deals for your flights.
Book early or wait unitl the last minute.
It's always better to book early. Flight tickets tend to be the cheapest when they are first released, normally about a year before the departure date. So, check online as soon as the flights you want become available. If you miss the cheapest time, you can still find lower-priced tickets as the flight date approaches.
Search for flights on the go.
To get the best flight booking experience on the go, download Trip.com and search for cheap flight tickets from Portland to Chicago to get exclusive deals for you.
Flight Info | Portland to Chicago
| Cheapest one-way flight price | AED 297 |
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| Cheapest return ticket price | AED 883 |
| Off-season for travel | March |
| Peak season for travel | June |
| Flight distance | 1,425.81 km |
| Average flight time | 5 hours 4 minutes |
| Popular airline | Jetblue Airways |
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