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$95+ 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 6/26. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PDX
May 17 — May 241
Sat 5/17
Sat 5/24
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 May 12, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$213
(Mytrip)

One-way from

$95
(Flightnetwork)

Popular in

December

Cheapest in

September

Average price

$275

Good round-trip deal

$270 or less

Good one-way deal

$118 or less
Provider with most accurate pricing for Chicago (CHI)-Portland flight deals.
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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. 6% potential increase in price ($20 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($11 potential savings vs. average RT price).
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Average for round-trip flights in May 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 May 12, 2025.

This Alaska Airlines deal was found by Cheapflights users on 5/11. 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 8/316:20 amORD - PDX
1 stop8h 04mAlaska Airlines
Sat 9/67:00 amPDX - ORD
Nonstop4h 09mAlaska Airlines
Deal found 5/11$213
This FlightHub deal was found by Cheapflights users on 5/11. 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 6/89:56 pmORD - PDX
1 stop16h 59mMultiple Airlines
Thu 6/126:39 pmPDX - ORD
1 stop9h 33mMultiple Airlines
Deal found 5/11$214
This Southwest deal was found by Cheapflights users on 5/12. 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 5/244:15 pmMDW - PDX
Nonstop4h 20mSouthwest
Sat 6/712:30 pmPDX - MDW
1 stop6h 10mSouthwest
Deal found 5/12$215
This Hawaiian Airlines deal was found by Cheapflights users on 5/11. 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.
Wed 5/285:58 pmORD - PDX
1 stop7h 46mHawaiian Airlines
Wed 6/45:51 pmPDX - ORD
Nonstop4h 05mHawaiian Airlines
Deal found 5/11$215
This Mytrip deal was found by Cheapflights users on 5/11. 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.
Wed 6/257:42 amORD - PDX
2 stops29h 35mSpirit Airlines
Wed 7/232:55 pmPDX - ORD
1 stop12h 58mSpirit Airlines
Deal found 5/11$217
This Frontier deal was found by Cheapflights users on 5/12. 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 5/242:44 pmMDW - PDX
1 stop11h 33mFrontier
Sat 6/76:35 amPDX - MDW
1 stop12h 18mFrontier
Deal found 5/12$220
This Delta deal was found by Cheapflights users on 5/11. 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.
Wed 6/254:26 pmMDW - PDX
1 stop9h 33mDelta
Tue 7/112:52 amPDX - MDW
1 stop5h 52mDelta
Deal found 5/11$223
This Delta deal was found by Cheapflights users on 5/11. 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 8/316:00 amORD - PDX
1 stop9h 07mDelta
Fri 9/512:40 amPDX - ORD
1 stop5h 51mDelta
Deal found 5/11$223
This United Airlines deal was found by Cheapflights users on 5/12. 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.
Sat 8/27:55 pmORD - PDX
Nonstop4h 34mUnited Airlines
Wed 8/610:55 pmPDX - ORD
Nonstop4h 01mUnited Airlines
Deal found 5/12$227
This American Airlines deal was found by Cheapflights users on 5/11. 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.
Tue 6/312:08 pmORD - PDX
Nonstop4h 26mAmerican Airlines
Mon 6/912:09 amPDX - ORD
Nonstop3h 56mAmerican Airlines
Deal found 5/11$235
This Frontier deal was found by Cheapflights users on 5/11. 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.
Sun 5/187:35 amORD - PDX
1 stop11h 34mFrontier
Mon 5/191:15 pmPDX - ORD
1 stop13h 55mFrontier
Deal found 5/11$276
This Sun Country Air deal was found by Cheapflights users on 5/11. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/176:00 amORD - PDX
1 stop18h 46mSun Country Air
Sun 7/2011:59 pmPDX - ORD
1 stop15h 16mSun Country Air
Deal found 5/11$350

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 May 12, 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

Fri 5/30

10:00 am-12:42 pm

2 stops28h 42m

Portland

Sun 6/1

5:40 pm-10:55 am

1 stop15h 15m

$213

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Sun 6/8

9:56 pm-12:55 pm

1 stop16h 59m

Portland

Thu 6/12

6:39 pm-6:12 am

1 stop9h 33m

$214

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Sat 5/24

4:15 pm-6:35 pm

Nonstop4h 20m

Portland

Sat 6/7

12:30 pm-8:40 pm

1 stop6h 10m

$215

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Wed 5/28

5:58 pm-11:44 pm

1 stop7h 46m

Portland

Wed 6/4

5:51 pm-11:56 pm

Nonstop4h 05m

$215

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Fri 5/30

7:00 am-9:23 am

Nonstop4h 23m

Portland

Sun 6/1

7:00 am-1:08 pm

Nonstop4h 08m

$218

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Sat 5/24

2:44 pm-12:17 am

1 stop11h 33m

Portland

Tue 6/3

6:35 am-8:53 pm

1 stop12h 18m

$220

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Wed 6/25

4:26 pm-11:59 pm

1 stop9h 33m

Portland

Tue 7/1

12:52 am-8:44 am

1 stop5h 52m

$223

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Wed 6/25

6:15 pm-12:29 am

1 stop8h 14m

Portland

Tue 7/1

12:52 am-8:25 am

1 stop5h 33m

$223

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Sat 8/2

7:55 pm-10:29 pm

Nonstop4h 34m

Portland

Wed 8/6

10:55 pm-4:56 am

Nonstop4h 01m

$227

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Tue 6/3

12:08 pm-2:34 pm

Nonstop4h 26m

Portland

Mon 6/9

12:09 am-6:05 am

Nonstop3h 56m

$235

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/11

Showing 1-10 of 26 results
1
2
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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 May.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*2 stars
CheapflightsfaresPrice Accuracy3 starsTrust Score*2 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
CheapfaremartPrice Accuracy-Trust Score*1 star
CheapTicketsDealPrice Accuracy3 starsTrust Score*3 stars
Justfly.comPrice Accuracy3 starsTrust Score*2 stars
FlightnetworkPrice Accuracy-Trust Score*3 stars
Kiwi.comPrice Accuracy3 starsTrust Score*3 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 eDreams the most. eDreams 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 May 9, 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 $369). 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 May 12, 2025.

Unlike in the afternoon, when flights are generally more expensive, you can save up to 40% 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 May 11, 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.

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 May 12, 2025.

The most flights from CHI to PDX are scheduled on a Monday (24 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (13 on average).

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 May 12, 2025.
Read through reviews of airlines operating flights from Chicago to Portland, such as Alaska Airlines, Southwest and Delta. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Overall

8.0

Entertainment

7.1

Boarding

8.1

Comfort

7.9

Food

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Overall

8.0

Entertainment

7.1

Boarding

8.1

Comfort

7.9

Food

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Southwest
8.0
Very good
4,290 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Overall

8.0

Entertainment

7.1

Boarding

8.1

Comfort

7.9

Food

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Delta
8.0
Very good
7,950 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Overall

8.0

Entertainment

7.1

Boarding

8.1

Comfort

7.9

Food

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Hawaiian Airlines
7.9
Good
2,431 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Overall

8.0

Entertainment

7.1

Boarding

8.1

Comfort

7.9

Food

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
United Airlines
7.4
Good
8,724 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Overall

8.0

Entertainment

7.1

Boarding

8.1

Comfort

7.9

Food

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

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 19 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 $213 on this airline. Additional options worth looking into are Southwest and Hawaiian Airlines, starting at $215 and $215 round-trip. These flights start at 32% 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 Spirit Airlines. According to our data, you can fly for as low as $95. Users have also found prices from $99 and $100 on Southwest and Delta, 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 (93%), Alaska Airlines (93%) and United Airlines (91%).

  • What are the cheapest flights from Chicago to Portland?

    Looking at all options, your cheapest flight can be booked for $109. While the most popular route (Chicago O'Hare Intl - Portland) can be booked for $164 on average our data indicates $933 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 $369). 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
Seaside
Lincoln City
Beaverton
Clackamas
Vancouver
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Hillsboro
Gresham
Astoria
Long Beach
Cannon Beach
Tigard
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Woodburn
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Pacific City
Stevenson
Troutdale
Wilsonville

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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 May 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$83Average$137FlexibilityNo cancel feeOn-time65%
FrontierCheapest$108Average$183FlexibilityNo cancel feeOn-time62%
Hawaiian AirlinesCheapest$134Average$289FlexibilityNo cancel feeOn-time85%
DeltaCheapest$176Average$366FlexibilityNo cancel feeOn-timeN/A
Alaska AirlinesCheapest$178Average$287FlexibilityNo cancel feeOn-time75%
American AirlinesCheapest$201Average$341FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$219Average$384FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$238Average$444FlexibilityNo cancel feeOn-time63%

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