HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Portland

$109+ 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 4/25. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PDX
Mar 10 — Mar 171
Tue 3/10
Tue 3/17
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Chicago to Portland with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.
Cheapflights Tip: The best prices from Chicago to Portland are usually found in September or May, booked 60 days in advance, depart on a Wednesday or Tuesday and return on a Friday

Cheap 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 February 8, 2026.

This Trip.com deal was found by Cheapflights users on 2/5. 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.
Sat 2/282:07 pm
ORD
-
PDX
Nonstop4h 43m
Hawaiian Airlines
Sat 3/73:52 pm
PDX
-
ORD
1 stop6h 04m
Hawaiian Airlines
Deal found 2/5$205
This Southwest deal was found by Cheapflights users on 2/4. 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 2/288:30 pm
MDW
-
PDX
Nonstop4h 30m
Southwest
Sat 3/75:20 am
PDX
-
MDW
Nonstop3h 55m
Southwest
Deal found 2/4$207
This Alaska Airlines deal was found by Cheapflights users on 2/5. 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.
Wed 3/45:29 pm
ORD
-
PDX
1 stop8h 15m
Alaska Airlines
Sat 3/77:00 am
PDX
-
ORD
Nonstop4h 11m
Alaska Airlines
Deal found 2/5$207
This Southwest deal was found by Cheapflights users on 2/7. 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 2/288:30 pm
MDW
-
PDX
Nonstop4h 30m
Southwest
Wed 3/47:25 am
PDX
-
MDW
1 stop7h 50m
Southwest
Deal found 2/7$208
This SmartFares deal was found by Cheapflights users on 2/7. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/246:00 am
ORD
-
PDX
1 stop6h 33m
Hawaiian Airlines
Tue 3/312:42 pm
PDX
-
ORD
1 stop7h 17m
Hawaiian Airlines
Deal found 2/7$209
This Southwest deal was found by Cheapflights users on 2/8. 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 3/78:10 pm
MDW
-
PDX
1 stop7h 30m
Southwest
Sat 3/146:20 pm
PDX
-
MDW
1 stop9h 35m
Southwest
Deal found 2/8$211
This Kiwi.com deal was found by Cheapflights users on 2/7. 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.
Fri 3/67:23 pm
ORD
-
PDX
2 stops40h 46m
Multiple Airlines
Mon 3/912:04 pm
PDX
-
ORD
1 stop10h 53m
Multiple Airlines
Deal found 2/7$211
This Southwest deal was found by Cheapflights users on 2/6. 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 3/149:40 pm
MDW
-
PDX
1 stop11h 15m
Southwest
Sun 3/1511:55 pm
PDX
-
MDW
Nonstop3h 50m
Southwest
Deal found 2/6$214
This United Airlines deal was found by Cheapflights users on 2/4. 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.
Tue 2/244:15 pm
ORD
-
PDX
Nonstop4h 34m
United Airlines
Tue 3/311:59 pm
PDX
-
ORD
Nonstop3h 54m
United Airlines
Deal found 2/4$214
This American Airlines deal was found by Cheapflights users on 2/7. 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 5/239:20 pm
ORD
-
PDX
Nonstop4h 27m
American Airlines
Fri 5/2911:30 pm
PDX
-
ORD
Nonstop4h 01m
American Airlines
Deal found 2/7$215
This Kiwi.com deal was found by Cheapflights users on 2/5. 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.
Mon 4/137:55 am
ORD
-
PDX
2 stops31h 07m
Multiple Airlines
Fri 4/179:53 am
PDX
-
ORD
1 stop18h 53m
Multiple Airlines
Deal found 2/5$216
This Southwest deal was found by Cheapflights users on 2/7. 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.
Fri 4/109:50 pm
MDW
-
PDX
Nonstop4h 20m
Southwest
Thu 4/165:10 am
PDX
-
MDW
Nonstop3h 55m
Southwest
Deal found 2/7$217

Find 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 February 8, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$205
(Trip.com)

One-way from

$109
(Delta)

Popular in

March

Cheapest in

September

Average price

$309

Good round-trip deal

$241 or less

Good one-way deal

$108 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.
Search Deals
From Chicago (CHI) to Portland
Search Deals
One-way flight from Chicago (CHI) to Portland
Search Deals
Highest demand for flights based on searches. 5% potential increase in price ($19 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
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

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 February 8, 2026.
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

MDW - PDX

MDWPDX

Chicago Midway

Thu 4/23

9:50 pm-12:10 am

Nonstop4h 20m

Portland

Sat 4/25

11:55 pm-5:50 am

Nonstop3h 55m

$207

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Tue 3/10

4:40 pm-7:14 pm

Nonstop4h 34m

Portland

Fri 3/13

11:59 pm-5:53 am

Nonstop3h 54m

$207

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Thu 4/2

10:30 am-12:50 pm

Nonstop4h 20m

Portland

Tue 4/7

11:55 pm-5:50 am

Nonstop3h 55m

$207

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Tue 4/14

8:50 pm-11:10 pm

Nonstop4h 20m

Portland

Fri 4/17

11:55 pm-5:50 am

Nonstop3h 55m

$207

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Tue 2/24

4:15 pm-6:49 pm

Nonstop4h 34m

Portland

Tue 3/3

11:59 pm-5:53 am

Nonstop3h 54m

$214

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Sat 3/14

9:40 pm-6:55 am

1 stop11h 15m

Portland

Sun 3/15

11:55 pm-5:45 am

Nonstop3h 50m

$214

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Tue 4/14

1:36 pm-9:42 pm

1 stop10h 06m

Portland

Tue 4/21

5:30 am-4:39 pm

1 stop9h 09m

$217

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Wed 3/18

2:20 pm-8:59 pm

1 stop8h 39m

Portland

Wed 3/25

11:15 pm-9:10 am

1 stop7h 55m

$217

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Tue 4/7

4:03 pm-10:58 pm

1 stop8h 55m

Portland

Wed 4/8

11:59 pm-6:03 am

Nonstop4h 04m

$217

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Sat 5/9

12:30 pm-5:15 pm

1 stop6h 45m

Portland

Tue 5/19

5:17 am-1:33 pm

1 stop6h 16m

$217

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/6

Showing 1-10 of 44 results
1
2
3
...
5

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 February.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
Kiwi.comPrice Accuracy3 starsTrust Score*3 stars
JustAirTicketPrice Accuracy-Trust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars
CheapflightsfaresPrice Accuracy2 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.

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 January 30, 2026.

To ensure you get the cheapest price possible for a flight from Chicago to Portland, you should look to book at least 60 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, March is the cheapest month in which you can book a flight from Chicago to Portland (average of $122). Flying from Chicago to Portland in December is currently the most expensive (average of $207). 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 February 8, 2026.

Unlike at noon, when flights are generally more expensive, you can save up to 25% 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 January 31, 2026.

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

How much does it cost to fly round-trip from Chicago to Portland?

The best insider tips for Chicago to Portland flights

AI-powered summary based on content written by travel experts. AI can make mistakes.
Cheapflights partnered with top experts to bring you the best recommendations for your Chicago to Portland trip
Our travel experts
Robert Schrader

Robert Schrader

Expert on Alaska Airlines

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 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

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 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

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 February 8, 2026.
Read through reviews of airlines operating flights from Chicago to Portland, such as Alaska Airlines, Southwest, and Hawaiian Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
11,851 reviews

Entertainment

7.0

Overall

8.0

Boarding

8.1

Comfort

7.8

Food

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Anonymous,Jan 2026

STS - LAX

Enjoyed staff assistance from ticking thru tsa , boarding and in the plane Couldn’t pick a seat except upgrading
Alaska Airlines
8.0
Very good
11,851 reviews
Alaska Airlines
8.0
Very good
11,851 reviews

Entertainment

7.0

Overall

8.0

Boarding

8.1

Comfort

7.8

Food

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Anonymous,Jan 2026

STS - LAX

Enjoyed staff assistance from ticking thru tsa , boarding and in the plane Couldn’t pick a seat except upgrading
Southwest
8.0
Very good
4,280 reviews
Alaska Airlines
8.0
Very good
11,851 reviews

Entertainment

7.0

Overall

8.0

Boarding

8.1

Comfort

7.8

Food

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Anonymous,Jan 2026

STS - LAX

Enjoyed staff assistance from ticking thru tsa , boarding and in the plane Couldn’t pick a seat except upgrading
Hawaiian Airlines
7.8
Good
2,829 reviews
Alaska Airlines
8.0
Very good
11,851 reviews

Entertainment

7.0

Overall

8.0

Boarding

8.1

Comfort

7.8

Food

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Anonymous,Jan 2026

STS - LAX

Enjoyed staff assistance from ticking thru tsa , boarding and in the plane Couldn’t pick a seat except upgrading
United Airlines
7.4
Good
9,254 reviews
Alaska Airlines
8.0
Very good
11,851 reviews

Entertainment

7.0

Overall

8.0

Boarding

8.1

Comfort

7.8

Food

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Anonymous,Jan 2026

STS - LAX

Enjoyed staff assistance from ticking thru tsa , boarding and in the plane Couldn’t pick a seat except upgrading
American Airlines
7.2
Good
11,249 reviews
Alaska Airlines
8.0
Very good
11,851 reviews

Entertainment

7.0

Overall

8.0

Boarding

8.1

Comfort

7.8

Food

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Anonymous,Jan 2026

STS - LAX

Enjoyed staff assistance from ticking thru tsa , boarding and in the plane Couldn’t pick a seat except upgrading

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 8 inbound flights from Chicago per day. 8 airlines have flights to Portland from Chicago on a regular basis.

  • How long is the flight from Chicago to Portland?

    Airlines like Southwest, United Airlines, and Delta fly from Chicago to Portland in about 4h 20m. The time it takes to get you to your destination can typically vary by up to 5h 46m. Airlines will cover a distance of 1746 mi. This flight may include one or multiple stops.

  • 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 $86 on this airline. Additional options worth looking into are Delta and Hawaiian Airlines, starting at $88 and $128 round-trip. These flights start at 73% 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 $90. Users have also found prices from $90 and $96 on Hawaiian Airlines and Frontier, respectively.

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

    The top 3 most reliable airlines when flying from Chicago to Portland are Alaska Airlines (80%), Hawaiian Airlines (80%) and Qatar Airways (75%).

  • What are the cheapest flights from Chicago to Portland?

    Looking at all options, your cheapest flight can be booked for $108. While the most popular route (Chicago O'Hare Intl - Portland) can be booked for $177 on average, our data indicates $624 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, March is the cheapest month in which you can book a flight from Chicago to Portland (average of $122). Flying from Chicago to Portland in December is currently the most expensive (average of $207). 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
Clackamas
Lincoln City
Longview
Lake Oswego
Beaverton
Hillsboro
Troutdale
Cannon Beach
Long Beach
McMinnville
Tigard
The Dalles
Depoe Bay
Wilsonville
Stevenson
Tillamook
Pacific City
Gresham

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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 February 8, 2026.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$86Average$178FlexibilityNo cancel feeOn-time65%
DeltaCheapest$88Average$328FlexibilityNo cancel feeOn-timeN/A
Hawaiian AirlinesCheapest$128Average$272FlexibilityNo cancel feeOn-time85%
FrontierCheapest$150Average$227FlexibilityNo cancel feeOn-time62%
Alaska AirlinesCheapest$194Average$307FlexibilityNo cancel feeOn-time75%
United AirlinesCheapest$202Average$350FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$204Average$312FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$234Average$413FlexibilityNo cancel feeOn-time63%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.