AED 203 Cheap Flights from Chicago to Portland
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Flights from Chicago to Portland
Cheap flight deals from Chicago to Portland Starting at AED 203
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
ORD 20:204h 42mNonstopPDX 23:02Chicago - Portland | Sat, May 3 | American Airlines
PDX 15:244h 5mNonstopORD 21:29Portland - Chicago | Wed, May 7 | American AirlinesAED 670 AED 97331% OFF31% OFFAED 973 AED 670 -
ORD 20:204h 42mNonstopPDX 23:02Chicago - Portland | Sat, Apr 19 | American Airlines
PDX 23:524h 5mNonstopORD 05:57Portland - Chicago | Sat, Apr 26 | American AirlinesAED 759 AED 97322% OFF22% OFFAED 973 AED 759
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ORD 19:3915h 8m1 stopsPDX 08:47Chicago - Portland | Thu, Apr 3 | Frontier Airlines
PDX 15:227h 41m1 stopsORD 01:03Portland - Chicago | Wed, Apr 9 | Frontier AirlinesAED 430 AED 97356% OFF56% OFFAED 973 AED 430 -
ORD 08:008h 22m1 stopsPDX 14:22Chicago - Portland | Wed, Apr 16 | Frontier Airlines
PDX 09:0114h 2m1 stopsORD 01:03Portland - Chicago | Mon, Apr 21 | Frontier AirlinesAED 44854% OFFAED 973 AED 448
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MDW 06:4519h 52m1 stopsPDX 00:37Chicago - Portland | Mon, Apr 7 | Frontier Airlines
PDX 09:5412h 21m1 stopsORD 00:15Portland - Chicago | Tue, Apr 8 | Frontier AirlinesAED 45553% OFFAED 973 AED 455
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MDW 06:4019h 57m1 stopsPDX 00:37Chicago - Portland | Tue, Apr 8 | Frontier Airlines
PDX 09:5412h 21m1 stopsORD 00:15Portland - Chicago | Tue, Apr 15 | Frontier AirlinesAED 45653% OFFAED 973 AED 456
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MDW 20:5013h 57m1 stopsPDX 08:47Chicago - Portland | Thu, Apr 10 | Frontier Airlines
PDX 09:019h 13m1 stopsMDW 20:14Portland - Chicago | Mon, Apr 14 | Frontier AirlinesAED 46053% OFFAED 973 AED 460
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ORD 06:4519h 52m1 stopsPDX 00:37Chicago - Portland | Tue, Mar 25 | Frontier Airlines
PDX 09:5412h 21m1 stopsORD 00:15Portland - Chicago | Tue, Apr 1 | Frontier AirlinesAED 47451% OFFAED 973 AED 474
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MDW 20:5013h 57m1 stopsPDX 08:47Chicago - Portland | Wed, Apr 2 | Frontier Airlines
PDX 15:227h 41m1 stopsORD 01:03Portland - Chicago | Wed, Apr 9 | Frontier AirlinesAED 50248% OFFAED 973 AED 502
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MDW 20:5013h 57m1 stopsPDX 08:47Chicago - Portland | Fri, Apr 11 | Frontier Airlines
PDX 09:019h 13m1 stopsMDW 20:14Portland - Chicago | Mon, Apr 14 | Frontier AirlinesAED 50848% OFFAED 973 AED 508
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MDW 20:016h 41m1 stopsPDX 00:42Chicago - Portland | Mon, Apr 28 | Frontier Airlines
PDX 21:5111h 32m1 stopsMDW 11:23Portland - Chicago | Mon, May 5 | Frontier AirlinesAED 52346% OFFAED 973 AED 523
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MDW 06:4519h 52m1 stopsPDX 00:37Chicago - Portland | Wed, Apr 9 | Frontier Airlines
PDX 09:019h 13m1 stopsMDW 20:14Portland - Chicago | Mon, Apr 14 | Frontier AirlinesAED 52346% OFFAED 973 AED 523
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CHI 13:0017h 25m1 stopsPDX Invalid DateChicago - Portland | Sun, Mar 23 | Normal Airline
PDX 15:006hNonstopCHI 16:00Portland - Chicago | Tue, Mar 25 | Normal AirlineFind More FlightsFind More Flights
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Cheapest nonstop
ORD 14:044h 32mNonstopPDX 16:36Chicago - Portland | Sat, Apr 19 | Alaska AirlinesAED 324 AED 50235% OFF35% OFFAED 502 AED 324 -
ORD 14:074h 33mNonstopPDX 16:40Chicago - Portland | Wed, Apr 23 | Hawaiian AirlinesAED 392 AED 50222% OFF22% OFFAED 502 AED 392 -
MDW 06:4019h 57m1 stopsPDX 00:37Chicago - Portland | Wed, Apr 2 | Frontier AirlinesAED 203 AED 50260% OFF60% OFFAED 502 AED 203
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ORD 08:008h 22m1 stopsPDX 14:22Chicago - Portland | Wed, Apr 16 | Frontier AirlinesAED 20759% OFFAED 502 AED 207
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MDW 06:4019h 57m1 stopsPDX 00:37Chicago - Portland | Wed, Mar 26 | Frontier AirlinesAED 21756% OFFAED 502 AED 217
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MDW 06:4519h 52m1 stopsPDX 00:37Chicago - Portland | Tue, Apr 15 | Frontier AirlinesAED 22156% OFFAED 502 AED 221
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MDW 20:5013h 57m1 stopsPDX 08:47Chicago - Portland | Thu, Apr 3 | Frontier AirlinesAED 22755% OFFAED 502 AED 227
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MDW 06:4019h 57m1 stopsPDX 00:37Chicago - Portland | Mon, Apr 7 | Frontier AirlinesAED 23254% OFFAED 502 AED 232
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ORD 06:4519h 52m1 stopsPDX 00:37Chicago - Portland | Tue, Mar 25 | Frontier AirlinesAED 23653% OFFAED 502 AED 236
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MDW 06:4019h 57m1 stopsPDX 00:37Chicago - Portland | Thu, Apr 10 | Frontier AirlinesAED 24152% OFFAED 502 AED 241
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MDW 06:4019h 57m1 stopsPDX 00:37Chicago - Portland | Wed, Apr 9 | Frontier AirlinesAED 28443% OFFAED 502 AED 284
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ORD 08:0928h 11m1 stopsPDX 10:20Chicago - Portland | Wed, Apr 2 | Spirit AirlinesAED 28843% OFFAED 502 AED 288 -
CHI 13:0017h 25m1 stopsPDX Invalid DateChicago - Portland | Sun, Mar 23 | 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 Chicago (CHI) to Portland (PDX) the cheapest?
Airlines adjust prices for flights from Chicago to Portland 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 Chicago (CHI) to Portland (PDX) cost?
According to Trip.com's data, the lowest price is around AED 1,259. -
How long does it take to fly from Chicago (CHI) to Portland (PDX)?
It takes about 5 hours 51 minutes to fly from Chicago (CHI) to Portland (PDX). -
What are the most popular airlines that fly from Chicago (CHI) to Portland (PDX)?
Airlines with flights from Chicago (CHI) to Portland (PDX): Southwest Airlines, United Airlines, Hawaiian Airlines, Air Canada, Brussels Airlines, Lufthansa, Swiss Airlines and Alaska Airlines. -
What's the most popular airline for non-stop flights from Chicago (CHI) to Portland (PDX)?
United Airlines operates 1 non-stop flights from Chicago (CHI) to Portland (PDX). -
How many airports are there in Portland (PDX)?
There are 2 airport(s) near Portland (PDX): Hillsboro Airport and Portland International Airport.
How to find a cheap flight from Chicago to Portland
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 Chicago to Portland. Book your flights at the right time and save more.
Being flexible with your dates to get the cheapest Chicago to Portland ticket.
Tap "Date" on flight search bar to scan through the calender for Chicago to Portland airfare over next 6 months in 2025. If you would like to fly in next 3 months, it seems the cheapest date is on Sat, Apr 19 at AED 324 for one-way flights.
Compare cheap Chicago to Portland 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 Chicago to Portland. The cheapest airline operating is Alaska Airlines.
Set up a Price Alert
By setting up a Price Alert for your Chicago to Portland route, you can easily track the price of your airline tickets from without manually checking every day.
Don't miss cheap Chicago to Portland 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 Chicago to Portland to get exclusive deals for you.
Flight Info | Chicago to Portland
| Cheapest one-way flight price | AED 202 |
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| Cheapest return ticket price | AED 648 |
| Off-season for travel | March |
| Peak season for travel | December |
| Flight distance | 2,816.22 km |
| Average flight time | 5 hours 51 minutes |
| Popular airline | Alaska Airlines |
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