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$98+ Cheap flights from Chicago (CHI) to Portland (PDX)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 8/12. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PDX
Aug 7 — Aug 141
Thu 8/7
Thu 8/14
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Portland are usually found in September or January, booked 69 days in advance, depart on a Wednesday or Tuesday and return on a Friday

Cheap flight deals from Chicago to Portland

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Portland (PDX). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated August 2, 2025.

Round-trip from

$179
(Southwest)

One-way from

$98
(Kissandfly.com)

Popular in

December

Cheapest in

September

Average price

$282

Good round-trip deal

$166 or less

Good one-way deal

$144 or less
From Chicago (CHI) to Portland
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One-way flight from Chicago (CHI) to Portland
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Highest demand for flights based on searches. 4% potential increase in price ($14 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($9 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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Price to beat on a round-trip flight from Chicago (CHI) to Portland.
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Price to beat on a one-way flight from Chicago (CHI) to Portland.
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Find flight deals from Chicago to Portland

Cheapest flights from Chicago to Portland
Explore the most affordable flight options available from Chicago to Portland. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 2, 2025.

This Southwest deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/302:10 pmMDW - PDX
Nonstop4h 15mSouthwest
Sun 8/316:55 amPDX - MDW
Nonstop4h 00mSouthwest
Deal found 7/29$179
This American Airlines deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/307:00 amORD - PDX
Nonstop4h 24mAmerican Airlines
Sun 8/317:00 amPDX - ORD
Nonstop4h 07mAmerican Airlines
Deal found 7/31$179
This Cheapflightsfares deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/306:00 amORD - PDX
1 stop7h 12mSpirit Airlines
Mon 10/68:04 pmPDX - ORD
1 stop6h 45mSpirit Airlines
Deal found 7/31$182
This Alaska Airlines deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/317:00 amORD - PDX
Nonstop4h 25mAlaska Airlines
Tue 9/167:00 amPDX - ORD
Nonstop4h 11mAlaska Airlines
Deal found 7/31$188
This Kiwi.com deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/307:00 amORD - PDX
Nonstop4h 25mHawaiian Airlines
Sat 9/67:00 amPDX - ORD
Nonstop4h 11mHawaiian Airlines
Deal found 8/1$202
This Delta deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/256:00 amMDW - PDX
1 stop8h 59mDelta
Thu 10/3012:50 amPDX - MDW
1 stop6h 05mDelta
Deal found 7/30$208
This Delta deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/317:45 amORD - PDX
1 stop6h 28mDelta
Sat 9/207:15 amPDX - ORD
1 stop8h 05mDelta
Deal found 8/1$223
This FlightHub deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/3110:43 amORD - PDX
1 stop14h 02mMultiple Airlines
Sun 9/78:18 pmPDX - ORD
1 stop13h 33mMultiple Airlines
Deal found 7/31$225
This Frontier deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/92:44 pmMDW - PDX
1 stop10h 40mFrontier
Sat 8/166:35 amPDX - MDW
1 stop12h 19mFrontier
Deal found 7/29$238

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Portland that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated August 2, 2025.
Use the filters below to find and compare flights from Chicago to Portland that are best for you.

Fly from

Chicago

Fly to

Portland

Route

Depart

Return

Price

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Sat 8/23

7:00 am-9:25 am

Nonstop4h 25m

Portland

Sat 8/30

5:50 pm-11:59 pm

Nonstop4h 09m

$176

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Wed 10/1

6:00 am-7:04 pm

1 stop15h 04m

Portland

Sat 10/4

8:04 pm-4:49 am

1 stop6h 45m

$178

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Sat 8/30

2:10 pm-4:25 pm

Nonstop4h 15m

Portland

Sun 8/31

6:55 am-12:55 pm

Nonstop4h 00m

$179

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Sat 8/30

7:00 am-9:25 am

Nonstop4h 25m

Portland

Sun 8/31

7:00 am-1:09 pm

Nonstop4h 09m

$179

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Wed 10/1

7:25 am-9:47 am

Nonstop4h 22m

Portland

Tue 10/7

11:58 pm-5:53 am

Nonstop3h 55m

$197

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Fri 8/29

7:00 am-9:25 am

Nonstop4h 25m

Portland

Fri 9/5

8:18 pm-11:51 am

1 stop13h 33m

$206

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Sat 10/25

6:00 am-12:59 pm

1 stop8h 59m

Portland

Fri 10/31

11:36 am-10:14 pm

1 stop8h 38m

$208

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Wed 8/27

7:00 am-12:40 pm

1 stop7h 40m

Portland

Tue 9/2

9:05 pm-11:50 am

1 stop12h 45m

$222

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Sun 8/31

7:45 am-12:13 pm

1 stop6h 28m

Portland

Sat 9/20

7:15 am-5:20 pm

1 stop8h 05m

$223

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Sat 8/16

2:44 pm-11:24 pm

1 stop10h 40m

Portland

Fri 8/22

12:18 pm-12:24 am

1 stop10h 06m

$248

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/30

Showing 1-10 of 23 results
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The best insider tips for Chicago to Portland flights

Snippets provided in this section are AI-generated based on a summarization of Cheapflights-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
Cheapflights partnered with top experts to bring you the best recommendations for your Chicago to Portland trip
Airlines
Alaska Airlines

Alaska's Premium Class offers extra legroom and free cocktails, ideal for a comfortable flight.


Alaska Airlines' Wi-Fi is a bargain, perfect for getting work done on longer flights.

Read more about Alaska Airlinesby Robert Schrader
Spirit Airlines

Spirit's Big Front Seats offer 11 inches more legroom, perfect for working with a laptop.


Spirit's Economy Plus Bundle includes both carry-on and check-in bags, saving on extra fees.

Read more about Spirit Airlinesby Daniel Scheffler
Airports
ORD

Avoid long walks at ORD by using the free shuttle train between terminals outside of security.

Read more about ORDby Ramsey Qubein
MDW

Order food via the airport’s mobile system directly to your gate to save time and ensure you don't miss boarding.

Read more about MDWby Ramsey Qubein
PDX

Use the MAX light rail for a convenient 40-minute ride between PDX and Downtown Portland.

Read more about PDXby Brandon Schultz
Our travel experts
Robert Schrader

Robert Schrader

Expert on Alaska Airlines

Robert Schrader

Robert Schrader

One of the web's original travel bloggers, Robert launched his first site Leave Your Daily Hell in 2009. Since then, he's expanded into destination niche sites (one each for Japan, Thailand and Taiwan), in addition to having written for the inflight magazines of Singapore Airlines and Korean Air. Overall, he's visited nearly 100 countries, and flies business as often as possible.

Read more
Daniel Scheffler

Daniel Scheffler

Expert on Spirit Airlines

Daniel Scheffler

Daniel Scheffler

Daniel Scheffler is a travel writer, podcaster, and producer. Born in Africa, bred in Europe and now living in America he has traveled to 140 countries (and all 50 U.S. states). Plus he has stayed at over 2500 hotels across the globe. His original shows Everywhere and Without Maps (available on Spotify) showcase his beliefs, travel is about humanity and sharing that beauty. And thus it reminds you that you shouldn’t believe everything you think.

Read more
Ramsey Qubein

Ramsey Qubein

Expert on ORD and MDW

Ramsey Qubein

Ramsey Qubein

An avid traveler and aviation expert who has visited 173 countries, all 50 states and seven continents, Ramsey Qubein flies nearly 400,000 miles a year. As a North Carolina-based freelance journalist for publications including Conde Nast Traveler, Forbes, USA Today and Bloomberg among others, he explores the latest trends in aviation, hospitality, cruises and business.

Read more
Brandon Schultz

Brandon Schultz

Expert on PDX

Brandon Schultz

Brandon Schultz

Brandon Schultz is an award-winning food and travel writer based in New York City. His work has appeared in Forbes, AAA, Thrillist, Travel + Leisure, and The Daily Meal, among many others, and he is the author of 6 books, including 3 cookbooks.

Read more

Best time to book a flight from Chicago to Portland

Have a flexible travel schedule? Discover the best time to fly to Portland from Chicago with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chicago to Portland

What is the cheapest month to book a flight from Chicago to Portland?

Currently, November is the cheapest month in which you can book a flight from Chicago to Portland (average of $277). Flying from Chicago to Portland in March is currently the most expensive (average of $368). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from CHI to PDX?

Find hourly flight availability from Chicago to Portland. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated August 2, 2025.

Unlike at noon, when flights are generally more expensive, you can save up to 26% on flights from Chicago to Portland by exploring options for tickets in the evening.

What is the cheapest day to fly from Chicago to Portland?

Use this chart to determine the cheapest time to fly round-trip from Chicago to Portland. Price data was last updated on July 27, 2025.

Travelers seeking maximum savings on their Chicago to Portland flight should consider departing on Tuesday evenings when fares are most often at their lowest. Monday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Chicago to Portland

Explore weekly flight availability from Chicago to Portland. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated August 2, 2025.

The most flights from CHI to PDX are scheduled on a Saturday (29 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (8 on average).

What’s the top layover airport for flights from Chicago to Portland?

Share of 1-stop round-trip flights from Chicago to Portland chosen by Cheapflights users in the past 12 months, using the same layover each way.

Las Vegas (LAS) – chosen by Cheapflights users on 97% of 1-stop itineraries from Chicago to Portland on Cheapflights.

What’s the cheapest layover airport for flights from Chicago to Portland?

Average round-trip fare for 1-stop flights from Chicago to Portland, chosen by Cheapflights users in the past 12 months, with the same layover each way.

Denver (DEN) is the most affordable 1-stop option, with an average round-trip price of $138.

What’s the fastest layover option from Chicago to Portland?

Shortest average travel time for 1-stop one-way flights from Chicago to Portland, based on itineraries clicked by Cheapflights users over the past 12 months, grouped by layover airport.

Flights via Denver (DEN) have the shortest average one-way travel time for 1-stop routes: 7h 58m.

Which airport typically offers the quickest layover for flights from Chicago to Portland?

Average layover duration for 1-stop one-way flights from Chicago to Portland, chosen by Cheapflights users in the last 12 months, grouped by stopover airport.

Flights via Denver (DEN) offer the fastest connection on this route, with an average layover time of 5h 46m.

Reviews of airlines servicing Portland

Get insights into the airlines that provide service to Portland. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Portland. Reviews last updated August 2, 2025.
Read through reviews of airlines operating flights from Chicago to Portland, such as Alaska Airlines, Southwest, and Delta. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Entertainment

7.1

Comfort

7.8

Boarding

8.1

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Entertainment

7.1

Comfort

7.8

Boarding

8.1

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Southwest
8.0
Very good
4,246 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Entertainment

7.1

Comfort

7.8

Boarding

8.1

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Delta
8.0
Very good
7,983 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Entertainment

7.1

Comfort

7.8

Boarding

8.1

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Hawaiian Airlines
7.8
Good
2,613 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Entertainment

7.1

Comfort

7.8

Boarding

8.1

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
United Airlines
7.4
Good
8,904 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Entertainment

7.1

Comfort

7.8

Boarding

8.1

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.

Related info for your journey

Find useful and relevant information for your journey from Chicago to Portland. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Portland from Chicago?

    For a flight from Chicago to Portland, you will be flying into Portland. Portland (PDX) is just 6.0 mi from the center of the city. Portland is the only Portland airport and it handles 18 inbound flights from Chicago per day. 8 airlines have flights to Portland from Chicago on a regular basis.

  • What are the cheapest airlines flying from Chicago to Portland round-trip?

    Our cheapest airline available from Chicago to Portland is Southwest. Our recent data shows that you can find tickets from as low as $179 on this airline. Additional options worth looking into are American Airlines and Spirit Airlines, starting at $179 and $182 round-trip. These flights start at 44% lower than the current average price 3 months from now.

  • What are the cheapest airlines to fly from Chicago to Portland one-way?

    For one-way options, check prices for Alaska Airlines. According to our data, you can fly for as low as $98. Users have also found prices from $99 and $99 on Southwest and Hawaiian Airlines, respectively.

  • What are the most reliable airlines from Chicago to Portland?

    The top 3 most reliable airlines when flying from Chicago to Portland are Brussels Airlines (83%), United Airlines (80%) and American Airlines (79%).

  • What are the cheapest flights from Chicago to Portland?

    Looking at all options, your cheapest flight can be booked for $96. While the most popular route (Chicago O'Hare Intl - Portland) can be booked for $171 on average our data indicates $760 when flying from Chicago to Portland.

  • Can I find deals for flights from Chicago to Portland that include hotel bookings?

    Yes. In addition to deals on Chicago to Portland flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Portland?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Portland.

  • Can I find deals for business class flights from Chicago to Portland?

    Yes. Cheapflights offers flight deals from Chicago to Portland by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago to Portland?

    Currently, November is the cheapest month in which you can book a flight from Chicago to Portland (average of $277). Flying from Chicago to Portland in March is currently the most expensive (average of $368). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Portland?

Book flights to Portland if you plan to visit one of these locations
Vancouver
Seaside
Beaverton
Clackamas
Lincoln City
McMinnville
Lake Oswego
Hillsboro
Astoria
Cannon Beach
Long Beach
Longview
Tigard
Depoe Bay
Woodburn
Stevenson
Wilsonville
Pacific City
Troutdale
Tillamook

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for Chicago to Portland

See prices for flight routes from nearby airports that may be better suited for you.
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Top 8 airlines flying from Chicago to Portland

Discover the top 8 airlines that operate flights from Chicago to Portland. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated August 2, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$81Average$179FlexibilityNo cancel feeOn-time65%
FrontierCheapest$108Average$179FlexibilityNo cancel feeOn-time62%
DeltaCheapest$123Average$327FlexibilityNo cancel feeOn-timeN/A
Hawaiian AirlinesCheapest$134Average$288FlexibilityNo cancel feeOn-time85%
Alaska AirlinesCheapest$181Average$287FlexibilityNo cancel feeOn-time75%
United AirlinesCheapest$226Average$384FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$227Average$328FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$238Average$433FlexibilityNo cancel feeOn-time63%

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