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$110+ 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 5/28. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PDX
avr. 2 — avr. 91
mer. 4/2
mer. 4/9
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Portland are usually found in September or January, booked 24 days in advance, depart on a Wednesday or Tuesday and return on a Wednesday

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 mars 28, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$241
(Mytrip)

One-way from

$110
(Alaska Airlines)

Popular in

March

Cheapest in

September

Average price

$447

Good round-trip deal

$288 or less

Good one-way deal

$155 or less
Provider with most accurate pricing for Chicago (CHI)-Portland flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Portland flights.
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From Chicago (CHI) to Portland
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One-way flight from Chicago (CHI) to Portland
Search Deals
Highest demand for flights based on searches. 10% potential increase in price ($39 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($12 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 2025
Search Deals
Price to beat on a round-trip flight from Chicago (CHI) to Portland.
Search Deals
Price to beat on a one-way flight from Chicago (CHI) to Portland.
Search Deals

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 mars 28, 2025.

This Mytrip deal was found by Cheapflights users on 3/27. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 4/2110:26 pmORD - PDX
2 stops21h 39mSpirit Airlines
mer. 4/232:32 pmPDX - ORD
2 stops13h 13mSpirit Airlines
Deal found 3/27$241
This Southwest deal was found by Cheapflights users on 3/26. 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.
sam. 4/194:15 pmMDW - PDX
Nonstop4h 20mSouthwest
sam. 4/2611:50 amPDX - MDW
1 stop8h 25mSouthwest
Deal found 3/26$242
This American Airlines deal was found by Cheapflights users on 3/28. 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.
mer. 4/238:20 pmORD - PDX
Nonstop4h 42mAmerican Airlines
lun. 4/2811:52 pmPDX - ORD
Nonstop4h 05mAmerican Airlines
Deal found 3/28$243
This Mytrip deal was found by Cheapflights users on 3/28. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jeu. 5/18:05 pmORD - PDX
1 stop17h 14mMultiple Airlines
dim. 5/47:01 pmPDX - ORD
2 stops32h 44mMultiple Airlines
Deal found 3/28$244
This United Airlines deal was found by Cheapflights users on 3/27. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 7/151:04 pmORD - PDX
1 stop6h 27mUnited Airlines
mar. 7/227:35 pmPDX - ORD
1 stop8h 04mUnited Airlines
Deal found 3/27$247
This Hawaiian Airlines deal was found by Cheapflights users on 3/26. 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 Hawaiian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jeu. 4/173:16 pmORD - PDX
Nonstop4h 34mHawaiian Airlines
sam. 4/197:00 amPDX - ORD
Nonstop4h 05mHawaiian Airlines
Deal found 3/26$248
This Delta deal was found by Cheapflights users on 3/27. 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.
sam. 4/195:59 pmMDW - PDX
1 stop6h 36mDelta
sam. 4/2610:59 pmPDX - MDW
1 stop7h 41mDelta
Deal found 3/27$251
This CheapOair deal was found by Cheapflights users on 3/27. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jeu. 4/106:45 amORD - PDX
1 stop19h 52mFrontier
dim. 4/209:27 pmPDX - ORD
1 stop29h 41mFrontier
Deal found 3/27$251
This Frontier deal was found by Cheapflights users on 3/27. 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.
ven. 4/118:36 pmMDW - PDX
1 stop14h 20mFrontier
mar. 4/159:59 amPDX - MDW
1 stop12h 22mFrontier
Deal found 3/27$258
This Delta deal was found by Cheapflights users on 3/27. 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.
jeu. 4/246:25 pmORD - PDX
1 stop7h 31mDelta
mar. 4/295:10 amPDX - ORD
1 stop6h 09mDelta
Deal found 3/27$262
This Alaska Airlines deal was found by Cheapflights users on 3/27. 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.
lun. 6/97:00 amORD - PDX
Nonstop4h 23mAlaska Airlines
ven. 6/135:35 pmPDX - ORD
Nonstop4h 04mAlaska Airlines
Deal found 3/27$263
This Trip.com deal was found by Cheapflights users on 3/27. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ven. 4/118:36 pmMDW - PDX
1 stop14h 20mMultiple Airlines
dim. 4/1310:25 amPDX - MDW
1 stop16h 55mMultiple Airlines
Deal found 3/27$289

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 mars 28, 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

lun. 4/21

10:26 pm-6:05 pm

2 stops21h 39m

Portland

mer. 4/23

2:32 pm-5:45 am

2 stops13h 13m

$241

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

sam. 4/19

4:15 pm-6:35 pm

Nonstop4h 20m

Portland

sam. 4/26

11:50 am-10:15 pm

1 stop8h 25m

$242

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

jeu. 4/24

8:20 pm-11:02 pm

Nonstop4h 42m

Portland

mar. 4/29

11:52 pm-5:57 am

Nonstop4h 05m

$242

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

jeu. 5/1

8:05 pm-11:19 am

1 stop17h 14m

Portland

dim. 5/4

11:02 am-12:31 am

2 stops35h 29m

$244

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

sam. 4/26

5:25 pm-10:25 pm

1 stop7h 00m

Portland

mar. 4/29

8:55 am-4:45 pm

1 stop5h 50m

$246

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

mer. 6/4

7:15 pm-11:43 pm

1 stop6h 28m

Portland

mer. 6/18

11:13 pm-7:50 am

1 stop6h 37m

$247

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

jeu. 4/17

3:16 pm-5:50 pm

Nonstop4h 34m

Portland

sam. 4/19

7:00 am-1:05 pm

Nonstop4h 05m

$248

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

sam. 4/19

5:59 pm-10:35 pm

1 stop6h 36m

Portland

sam. 4/26

10:59 pm-8:40 am

1 stop7h 41m

$251

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

jeu. 4/24

4:12 pm-6:45 pm

Nonstop4h 33m

Portland

lun. 4/28

11:59 pm-5:56 am

Nonstop3h 57m

$253

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

ven. 4/11

8:36 pm-8:56 am

1 stop14h 20m

Portland

mar. 4/15

9:59 am-12:21 am

1 stop12h 22m

$258

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/26

Showing 1-10 of 29 results
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Compare providers for flights from Chicago to Portland

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Chicago to Portland in March.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
CheapflightsfaresPrice Accuracy3 starsTrust Score*2 stars
CheapfaremartPrice Accuracy-Trust Score*3 stars
CheapTicketsDealPrice Accuracy3 starsTrust Score*3 stars
Justfly.comPrice Accuracy3 starsTrust Score*3 stars
FlightnetworkPrice Accuracy-Trust Score*3 stars
Kiwi.comPrice Accuracy3 starsTrust Score*2 stars
Trip.comPrice Accuracy1 starTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago-Portland flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Portland flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago-Portland flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago-Portland flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago-Portland flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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
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

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

How far ahead should I book a flight from Chicago to Portland?

Use this chart to determine the optimal time to book a round-trip flight from Chicago to Portland. Price data was last updated on March 21, 2025.

To ensure you get the cheapest price possible for a flight from Chicago to Portland, you should look to book at least 24 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

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 $370). 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 mars 28, 2025.

Unlike in the afternoon, when flights are generally more expensive, you can save up to 44% 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 March 23, 2025.

Travelers seeking maximum savings on their Chicago to Portland flight should consider departing on Saturday 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.

Rainfall in Portland by month

Plan your trip to Portland by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Portland ranges from 0.7 - 5.6 inches per month. November is typically the wettest month, when rainfall can reach 5.6 in. July is typically the driest time to visit Portland when rainfall is around 0.7 in.

Temperature in Portland by month

Plan your trip to Portland by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Portland, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 69.8 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 41.0 F).

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 mars 28, 2025.
Read through reviews of airlines operating flights from Chicago to Portland, such as Southwest, Alaska Airlines and Delta. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,274 reviews

Comfort

8.1

Crew

8.7

Food

7.1

Entertainment

7.6

Boarding

8.2

Overall

8.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Southwest
8.1
Very good
4,274 reviews
Southwest
8.1
Very good
4,274 reviews

Comfort

8.1

Crew

8.7

Food

7.1

Entertainment

7.6

Boarding

8.2

Overall

8.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Alaska Airlines
8.0
Very good
9,798 reviews
Southwest
8.1
Very good
4,274 reviews

Comfort

8.1

Crew

8.7

Food

7.1

Entertainment

7.6

Boarding

8.2

Overall

8.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Delta
8.0
Very good
7,897 reviews
Southwest
8.1
Very good
4,274 reviews

Comfort

8.1

Crew

8.7

Food

7.1

Entertainment

7.6

Boarding

8.2

Overall

8.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Hawaiian Airlines
7.9
Good
2,336 reviews
Southwest
8.1
Very good
4,274 reviews

Comfort

8.1

Crew

8.7

Food

7.1

Entertainment

7.6

Boarding

8.2

Overall

8.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
United Airlines
7.4
Good
8,603 reviews
Southwest
8.1
Very good
4,274 reviews

Comfort

8.1

Crew

8.7

Food

7.1

Entertainment

7.6

Boarding

8.2

Overall

8.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

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 5 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 Spirit Airlines. Our recent data shows that you can find tickets from as low as $241 on this airline. Additional options worth looking into are Southwest and American Airlines, starting at $242 and $242 round-trip. These flights start at 24% 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 $110. Users have also found prices from $112 and $114 on Spirit Airlines and Southwest, 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 (90%), Hawaiian Airlines (85%) and Qatar Airways (84%).

  • What are the cheapest flights from Chicago to Portland?

    Looking at all options, your cheapest flight can be booked for $113. While the most popular route (Chicago O'Hare Intl - Portland) can be booked for $178 on average our data indicates $612 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 $370). 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 Chicago?

Book flights to Chicago if you plan to visit one of these locations
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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 mars 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$82Average$138FlexibilityNo cancel feeOn-time65%
FrontierCheapest$108Average$190FlexibilityNo cancel feeOn-time62%
Hawaiian AirlinesCheapest$173Average$303FlexibilityNo cancel feeOn-time85%
Alaska AirlinesCheapest$176Average$288FlexibilityNo cancel feeOn-time75%
DeltaCheapest$176Average$366FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$196Average$334FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$218Average$390FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$237Average$432FlexibilityNo cancel feeOn-time63%
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