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$152+ 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 5/30. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PDX
Jun 11 — Jun 181
Thu 6/11
Thu 6/18
1 adult, Economy
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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”

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3. Compare prices and book

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Cheapflights Tip: The best prices from Chicago to Portland are usually found in January or February, booked 55 days in advance, depart on a Tuesday or Wednesday and return on a Wednesday

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 May 12, 2026.

This Southwest deal was found by Cheapflights users on 5/7. 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 5/299:50 pm
MDW
-
PDX
Nonstop4h 20m
Southwest
Wed 7/111:30 pm
PDX
-
MDW
Nonstop3h 50m
Southwest
Deal found 5/7$305
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.
Thu 5/282:18 pm
ORD
-
PDX
Nonstop4h 32m
Alaska Airlines
Wed 7/110:59 pm
PDX
-
ORD
Nonstop4h 01m
Alaska Airlines
Deal found 5/11$305
This Kiwi.com deal was found by Cheapflights users on 5/8. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/209:48 pm
ORD
-
PDX
1 stop21h 09m
Frontier
Thu 8/2712:26 pm
PDX
-
ORD
2 stops17h 37m
Frontier
Deal found 5/8$306
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/227:20 am
ORD
-
PDX
1 stop14h 27m
Multiple Airlines
Wed 6/2410:59 pm
PDX
-
ORD
Nonstop4h 01m
Multiple Airlines
Deal found 5/11$308
This Kiwi.com deal was found by Cheapflights users on 5/7. 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.
Thu 6/48:03 pm
MDW
-
PDX
1 stop20h 16m
Multiple Airlines
Sun 6/74:06 pm
PDX
-
MDW
2 stops27h 56m
Multiple Airlines
Deal found 5/7$309
This Kiwi.com deal was found by Cheapflights users on 5/10. 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 6/137:20 am
ORD
-
PDX
Nonstop4h 25m
Alaska Airlines
Fri 7/310:59 pm
PDX
-
ORD
Nonstop4h 01m
Alaska Airlines
Deal found 5/10$309
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.
Fri 7/34:40 pm
MDW
-
PDX
Nonstop4h 20m
Southwest
Sat 7/1111:30 pm
PDX
-
MDW
Nonstop3h 50m
Southwest
Deal found 5/12$310
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.
Fri 7/37:20 am
ORD
-
PDX
Nonstop4h 25m
Alaska Airlines
Tue 7/710:59 pm
PDX
-
ORD
Nonstop4h 01m
Alaska Airlines
Deal found 5/11$310
This Southwest deal was found by Cheapflights users on 5/7. 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 7/35:00 am
MDW
-
PDX
1 stop6h 55m
Southwest
Tue 7/711:30 pm
PDX
-
MDW
Nonstop3h 50m
Southwest
Deal found 5/7$311
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.
Sat 6/2710:00 pm
ORD
-
PDX
Nonstop4h 20m
American Airlines
Fri 7/31:45 pm
PDX
-
ORD
Nonstop4h 05m
American Airlines
Deal found 5/11$311
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/272:19 pm
ORD
-
PDX
Nonstop4h 35m
Alaska Airlines
Fri 7/310:59 pm
PDX
-
ORD
Nonstop4h 01m
Alaska Airlines
Deal found 5/11$312
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/117:20 am
ORD
-
PDX
Nonstop4h 25m
Multiple Airlines
Sat 7/185:42 pm
PDX
-
ORD
1 stop10h 35m
Multiple Airlines
Deal found 5/11$313

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 May 12, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$305
(Southwest)

One-way from

$152
(Booking.com)

Popular in

March

Cheapest in

January

Average price

$320

Good round-trip deal

$305 or less

Good one-way deal

$163 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. 3% potential increase in price ($11 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($10 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 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 May 12, 2026.
Use the filters below to find and compare flights from Chicago to Portland that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Wed 7/22

7:00 am-9:34 am

Nonstop4h 34m

Portland

Wed 7/29

10:40 pm-4:45 am

Nonstop4h 05m

$315

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Tue 7/7

7:00 am-9:34 am

Nonstop4h 34m

Portland

Tue 7/14

11:40 pm-5:45 am

Nonstop4h 05m

$315

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Wed 7/22

9:10 pm-11:30 pm

Nonstop4h 20m

Portland

Wed 7/29

3:20 pm-12:05 am

1 stop6h 45m

$325

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Tue 6/2

6:05 pm-11:10 pm

1 stop7h 05m

Portland

Tue 6/30

11:30 pm-5:20 am

Nonstop3h 50m

$331

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Wed 7/22

1:49 pm-8:15 pm

1 stop8h 26m

Portland

Tue 7/28

12:33 am-8:37 am

1 stop6h 04m

$335

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Wed 6/24

2:09 pm-6:22 pm

1 stop6h 13m

Portland

Mon 7/27

12:33 am-8:30 am

1 stop5h 57m

$335

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Wed 6/24

5:05 am-10:00 am

1 stop6h 55m

Portland

Tue 7/28

11:30 pm-5:20 am

Nonstop3h 50m

$335

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Tue 7/28

7:20 am-9:45 am

Nonstop4h 25m

Portland

Sun 8/23

5:35 pm-11:41 pm

Nonstop4h 06m

$336

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Thu 7/16

7:20 am-9:45 am

Nonstop4h 25m

Portland

Thu 7/23

10:59 pm-5:00 am

Nonstop4h 01m

$337

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Thu 9/3

5:30 pm-8:03 pm

Nonstop4h 33m

Portland

Mon 9/7

7:16 am-1:29 pm

Nonstop4h 13m

$337

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/8

Showing 1-10 of 44 resultsSorted by cheapest first
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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*3 stars
Kiwi.comPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice Accuracy1 starTrust Score*3 stars
JustAirTicketPrice Accuracy-Trust Score*1 star
eDreamsPrice Accuracy2 starsTrust Score*3 stars
CheapflightsfaresPrice Accuracy2 starsTrust Score*1 star
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?

To ensure you get the cheapest price possible for a flight from Chicago to Portland, you should look to book at least 77 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, May is the cheapest month in which you can book a flight from Chicago to Portland (average of $89). Flying from Chicago to Portland in July is currently the most expensive (average of $632). 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, 2026.

Unlike at noon, when flights are generally more expensive, you can save up to 20% 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 9, 2026.

Travelers seeking maximum savings on their Chicago to Portland flight should consider departing on Saturday afternoons when fares are most often at their lowest. Sunday 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, 2026.

The most flights from CHI to PDX are scheduled on a Sunday (26 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (17 on average).

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 May 12, 2026.
Read through reviews of airlines operating flights from Chicago to Portland, such as Southwest,Alaska Airlines, andHawaiian Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,295 reviews

Crew

8.6

Overall

8.0

Entertainment

7.5

Food

7.0

Boarding

8.1

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Southwest
8.0
Very good
4,295 reviews
Southwest
8.0
Very good
4,295 reviews

Crew

8.6

Overall

8.0

Entertainment

7.5

Food

7.0

Boarding

8.1

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Alaska Airlines
7.9
Good
12,354 reviews
Southwest
8.0
Very good
4,295 reviews

Crew

8.6

Overall

8.0

Entertainment

7.5

Food

7.0

Boarding

8.1

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Hawaiian Airlines
7.8
Good
2,837 reviews
Southwest
8.0
Very good
4,295 reviews

Crew

8.6

Overall

8.0

Entertainment

7.5

Food

7.0

Boarding

8.1

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
United Airlines
7.4
Good
9,701 reviews
Southwest
8.0
Very good
4,295 reviews

Crew

8.6

Overall

8.0

Entertainment

7.5

Food

7.0

Boarding

8.1

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
American Airlines
7.1
Good
11,661 reviews
Southwest
8.0
Very good
4,295 reviews

Crew

8.6

Overall

8.0

Entertainment

7.5

Food

7.0

Boarding

8.1

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

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 22 inbound flights from Chicago per day. 7 airlines have flights to Portland from Chicago on a regular basis.

  • How long is the flight from Chicago to Portland?

    Airlines like United Airlines, Southwest, 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 4h 06m. 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 Hawaiian Airlines and Frontier, starting at $124 and $150 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 $86. Users have also found prices from $90 and $98 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 (88%), Hawaiian Airlines (73%) and United Airlines (71%).

  • What are the cheapest flights from Chicago to Portland?

    Looking at all options, your cheapest flight can be booked for $125. While the most popular route (Chicago O'Hare Intl - Portland) can be booked for $266 on average, our data indicates $672 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, May is the cheapest month in which you can book a flight from Chicago to Portland (average of $89). Flying from Chicago to Portland in July is currently the most expensive (average of $632). 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
Beaverton
Seaside
Vancouver
Lincoln City
Longview
Lake Oswego
Hillsboro
Clackamas
Troutdale
Cannon Beach
Long Beach
McMinnville
Tigard
The Dalles
Wilsonville
Depoe Bay
Stevenson
Tillamook
Astoria
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 7 airlines flying from Chicago to Portland

Discover the top 7 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, 2026.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$86Average$178FlexibilityNo cancel feeOn-time65%
Hawaiian AirlinesCheapest$124Average$249FlexibilityNo cancel feeOn-time85%
FrontierCheapest$150Average$248FlexibilityNo cancel feeOn-time62%
Alaska AirlinesCheapest$189Average$316FlexibilityNo cancel feeOn-time75%
American AirlinesCheapest$198Average$319FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$199Average$349FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$227Average$358FlexibilityNo cancel feeOn-time63%

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