Cheap Flights from Chicago to Portland
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Flights from Chicago to Portland
Airlines Flying from Chicago to Portland
Compare prices, find the option that best suits your travel needs, and enjoy a comfortable journey with a trusted airline.
Flight deals from Chicago to Portland
We've found these cheap flights for you. You can book one-way or return flight tickets.
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Round-trip
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One way
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Cheapest nonstop
ORD 07:004h 25mDirectPDX 09:25Chicago - Portland | Tue, Aug 5 | Hawaiian Airlines
PDX 17:354h 4mDirectORD 23:39Portland - Chicago | Tue, Aug 12 | Hawaiian Airlines£126 £17227% OFF27% OFF£172 £126 -
ORD 07:004h 25mDirectPDX 09:25Chicago - Portland | Tue, Aug 5 | Alaska Airlines
PDX 17:354h 4mDirectORD 23:39Portland - Chicago | Wed, Aug 13 | Alaska Airlines£128 £17226% OFF26% OFF£172 £128 -
ORD 07:004h 25mDirectPDX 09:25Chicago - Portland | Wed, Aug 13 | Hawaiian Airlines
PDX 17:354h 4mDirectORD 23:39Portland - Chicago | Wed, Aug 13 | Hawaiian Airlines£128 £17226% OFF26% OFF£172 £128
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ORD 07:004h 25mDirectPDX 09:25Chicago - Portland | Sat, Aug 23 | Alaska Airlines
PDX 17:504h 9mDirectORD 23:59Portland - Chicago | Sat, Aug 30 | Alaska Airlines£12826% OFF£172 £128
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ORD 07:004h 25mDirectPDX 09:25Chicago - Portland | Wed, Aug 13 | Alaska Airlines
PDX 17:354h 4mDirectORD 23:39Portland - Chicago | Wed, Aug 13 | Hawaiian Airlines£12925% OFF£172 £129
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ORD 22:1513h 3m1 stopsPDX 09:18Chicago - Portland | Tue, Jul 8 | Spirit Airlines
PDX 15:1012h 53m1 stopsORD 06:03Portland - Chicago | Wed, Jul 9 | Spirit Airlines£11434% OFF£172 £114 -
ORD 14:0010h 1m1 stopsPDX 22:01Chicago - Portland | Wed, Jul 16 | Delta Air Lines
PDX 00:465h 39m1 stopsORD 08:25Portland - Chicago | Wed, Jul 23 | Delta Air Lines£12130% OFF£172 £121 -
MDW 13:088h 36m1 stopsPDX 19:44Chicago - Portland | Sat, Aug 23 | Delta Air Lines
PDX 13:368h 15m1 stopsORD 23:51Portland - Chicago | Wed, Aug 27 | Delta Air Lines£12130% OFF£172 £121
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ORD 17:598h1 stopsPDX 23:59Chicago - Portland | Tue, Aug 5 | Delta Air Lines
PDX 13:368h 15m1 stopsORD 23:51Portland - Chicago | Tue, Aug 12 | Delta Air Lines£12228% OFF£172 £122
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ORD 17:206h 41m1 stopsPDX 22:01Chicago - Portland | Tue, Jul 29 | Delta Air Lines
PDX 00:465h 59m1 stopsORD 08:45Portland - Chicago | Fri, Aug 1 | Delta Air Lines£12428% OFF£172 £124
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CHI 13:0017h 25m1 stopsPDX Invalid DateChicago - Portland | Sun, Jun 29 | Normal Airline
PDX 15:006hDirectCHI 16:00Portland - Chicago | Tue, Jul 1 | Normal AirlineFind More FlightsFind More Flights
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Cheapest nonstop
ORD 07:004h 25mDirectPDX 09:25Chicago - Portland | Sat, Aug 16 | Hawaiian Airlines£65 £9028% OFF28% OFF£90 £65
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ORD 07:004h 25mDirectPDX 09:25Chicago - Portland | Fri, Jul 4 | Alaska Airlines£65 £9028% OFF28% OFF£90 £65
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MDW 14:054h 20mDirectPDX 16:25Chicago - Portland | Fri, Jul 4 | Southwest Airlines£65 £9028% OFF28% OFF£90 £65 -
ORD 07:004h 25mDirectPDX 09:25Chicago - Portland | Sat, Aug 23 | Hawaiian Airlines£6528% OFF£90 £65
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ORD 07:004h 25mDirectPDX 09:25Chicago - Portland | Sat, Aug 23 | Alaska Airlines£6627% OFF£90 £66
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ORD 07:004h 25mDirectPDX 09:25Chicago - Portland | Sat, Aug 16 | Alaska Airlines£6627% OFF£90 £66
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ORD 07:004h 25mDirectPDX 09:25Chicago - Portland | Fri, Jul 4 | Hawaiian Airlines£6726% OFF£90 £67
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ORD 07:0017h 39m1 stopsPDX 22:39Chicago - Portland | Sat, Aug 23 | Frontier Airlines£6133% OFF£90 £61 -
ORD 11:507h 54m1 stopsPDX 17:44Chicago - Portland | Sat, Jun 28 | Spirit Airlines£6627% OFF£90 £66
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ORD 11:507h 54m1 stopsPDX 17:44Chicago - Portland | Wed, Jul 2 | Spirit Airlines£6825% OFF£90 £68
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CHI 13:0017h 25m1 stopsPDX Invalid DateChicago - Portland | Sun, Jun 29 | 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.
Flight Information from Chicago to Portland
| Cheapest one-way flight price | £61 |
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| Cheapest return ticket price | £114 |
| Off-season travel month | April |
| Peak season for travel | March |
| Flight distance | 2,816.22km |
| Average flight time | 4 hours 26 minutes |
| Popular airline | Hawaiian Airlines |
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Displayed prices are calculated based on the cheapest average weekly prices of the corresponding route on Trip.com.
FAQ
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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 cheapest flight prices on Tuesdays, Wednesdays, and Saturdays. -
How much are flights from Chicago (CHI) to Portland (PDX) cost?
According to Trip.com's data, the lowest price is around £252. -
How long is the flight from Chicago (CHI) to Portland (PDX)?
It takes about 4 hours 26 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): Qatar Airways, United Airlines, American Airlines, Hawaiian Airlines, Air Canada, Brussels Airlines, Lufthansa, Swiss, Malaysia Airlines and Southwest Airlines. -
How many airports in Portland (PDX)?
There are 2 airport(s) in 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.
Be flexible with your travel dates to get the cheapest flight from Chicago to Portland.
Simply tap "Date" on the flight search bar to browse through the calendar and check out airfare from Chicago to Portland over the next 6 months in 2025. If you're planning to fly within the next three months, it looks like the most affordable option is on Sat, Aug 16, with one-way flights priced at just £65.
Compare cheap flight deals from Chicago to Portland across hundreds of airlines.
With our extensive search, you can compare prices from over 500 airlines to find the cheapest flight tickets from Chicago to Portland. The cheapest airline for this route is Hawaiian Airlines.
Set up a Price Alert
By setting up a Price Alert for your journey from Chicago to Portland, you can easily keep an eye on ticket prices without having to check every day.
Don't miss out on cheap flight deals and promo codes from Chicago to Portland.
You can always find the latest offers through Trip.com Deals and Promo Codes for cheap flights. By signing up for a free membership, you'll get access to even more deals for your flights.
Book early or wait until the last minute.
It's usually best to book early. Flight tickets are often cheapest when they're first released, typically about a year before the departure date. So, have a look online as soon as the flights you're interested in become available. If you miss the cheapest time, you might still find some good deals as the departure date gets closer.
Search for flights on the go.
For the best travel flight booking experience, download the Trip.com app. You can search for cheap flights from Chicago to Portland and snag some exclusive deals just for you.
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