Portland

$134+ 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 4/21. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PDX
Apr 30 — May 71
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Find cheap flights from Chicago to Portland with Cheapflights

1. Tell us where you want to go

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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 May, booked 79 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 March 31, 2026.

This Trip.com 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/188:58 pm
ORD
-
PDX
1 stop14h 01m
Multiple Airlines
Sat 4/251:52 pm
PDX
-
ORD
1 stop8h 07m
Multiple Airlines
Deal found 3/28$213
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.
Tue 4/288:50 pm
MDW
-
PDX
Nonstop4h 20m
Southwest
Sat 5/211:55 pm
PDX
-
MDW
Nonstop3h 55m
Southwest
Deal found 3/26$215
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.
Wed 4/2212:46 pm
ORD
-
PDX
1 stop6h 24m
Delta
Tue 4/285:30 am
PDX
-
ORD
1 stop9h 09m
Delta
Deal found 3/27$215
This Super.com deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/308:58 pm
ORD
-
PDX
1 stop14h 01m
Frontier
Mon 5/49:54 am
PDX
-
ORD
1 stop17h 56m
Frontier
Deal found 3/30$216
This Booking.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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/308:58 pm
ORD
-
PDX
1 stop14h 01m
Frontier
Sun 5/39:54 am
PDX
-
ORD
1 stop18h 26m
Frontier
Deal found 3/27$218
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.
Wed 4/226:45 am
MDW
-
PDX
1 stop9h 05m
Southwest
Tue 4/287:00 am
PDX
-
MDW
2 stops10h 35m
Southwest
Deal found 3/26$220
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.
Wed 4/2911:55 am
ORD
-
PDX
2 stops12h 05m
Southwest
Wed 5/68:50 am
PDX
-
ORD
1 stop8h 00m
Southwest
Deal found 3/26$220
This Super.com 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/79:42 pm
ORD
-
PDX
1 stop21h 04m
Frontier
Sun 5/105:31 pm
PDX
-
ORD
1 stop11h 08m
Frontier
Deal found 3/28$221
This Booking.com deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/297:21 pm
ORD
-
PDX
1 stop18h 29m
Frontier
Sat 5/212:27 pm
PDX
-
ORD
1 stop19h 18m
Frontier
Deal found 3/30$223
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/298:00 pm
ORD
-
PDX
Nonstop4h 34m
United Airlines
Sat 5/21:35 pm
PDX
-
ORD
1 stop7h 54m
United Airlines
Deal found 3/26$225
This Expedia deal was found by Cheapflights users on 3/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/27:21 pm
ORD
-
PDX
1 stop18h 29m
Frontier
Thu 5/75:31 pm
PDX
-
ORD
1 stop11h 08m
Frontier
Deal found 3/29$226
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/188:58 pm
ORD
-
PDX
1 stop14h 01m
Multiple Airlines
Tue 4/217:15 am
PDX
-
ORD
1 stop9h 25m
Multiple Airlines
Deal found 3/28$231

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 March 31, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$213
(Trip.com)

One-way from

$134
(Kiwi.com)

Popular in

March

Cheapest in

January

Average price

$435

Good round-trip deal

$309 or less

Good one-way deal

$153 or less
Provider with most accurate pricing for Chicago (CHI)-Portland flight deals.
Provider most trusted by Cheapflights users for Chicago (CHI)-Portland flights.
From Chicago (CHI) to Portland
One-way flight from Chicago (CHI) to Portland
Highest demand for flights based on searches. 5% potential increase in price ($19 potential increase over avg. RT price).
Cheapest flight prices on average. 3% potential price decrease ($12 potential savings vs. average RT price).
Average for round-trip flights in March 2026
Price to beat on a round-trip flight from Chicago (CHI) to Portland.
Price to beat on a one-way flight from Chicago (CHI) to Portland.

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 March 31, 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

MDW - PDX

MDWPDX

Chicago Midway

Wed 4/22

4:00 pm-11:10 pm

2 stops9h 10m

Portland

Tue 4/28

5:00 pm-5:50 am

2 stops10h 50m

$225
Quickest round-trip

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Thu 4/16

9:50 pm-12:10 am

Nonstop4h 20m

Portland

Sat 4/18

11:55 pm-5:50 am

Nonstop3h 55m

$235

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Wed 5/6

8:50 pm-11:10 pm

Nonstop4h 20m

Portland

Sun 5/10

5:20 am-11:15 am

Nonstop3h 55m

$261

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Tue 5/19

11:55 am-9:00 pm

2 stops11h 05m

Portland

Tue 6/2

6:40 am-3:00 pm

1 stop6h 20m

$285

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Mon 5/11

6:00 am-12:52 pm

1 stop8h 52m

Portland

Tue 5/12

10:56 pm-5:05 am

Nonstop4h 09m

$297

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

$309

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Mon 6/22

7:05 am-9:39 am

Nonstop4h 34m

Portland

Sat 6/27

10:40 pm-4:45 am

Nonstop4h 05m

$316

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Wed 8/5

2:42 pm-10:13 pm

1 stop9h 31m

Portland

Wed 8/12

6:30 am-5:30 pm

1 stop9h 00m

$325

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Wed 5/13

11:55 am-10:00 pm

2 stops12h 05m

Portland

Fri 5/15

10:45 am-10:55 pm

2 stops10h 10m

$326

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Thu 9/24

7:00 am-9:28 am

Nonstop4h 28m

Portland

Mon 9/28

5:35 pm-11:41 pm

Nonstop4h 06m

$327

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/31

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 March.
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
PricelinePrice Accuracy1 starTrust 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 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 March 13, 2026.

To ensure you get the cheapest price possible for a flight from Chicago to Portland, you should look to book at least 79 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, January is the cheapest month in which you can book a flight from Chicago to Portland (average of $133). 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 March 31, 2026.

Unlike at noon, when flights are generally more expensive, you can save up to 19% 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 28, 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. 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 March 31, 2026.

The most flights from CHI to PDX are scheduled on a Tuesday (18 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (2 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.

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.

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.

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.

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 March 31, 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.

Comfort

8.0

Overall

8.0

Entertainment

7.5

Boarding

8.1

Food

7.0

Crew

8.6

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.

Comfort

8.0

Overall

8.0

Entertainment

7.5

Boarding

8.1

Food

7.0

Crew

8.6

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.

Comfort

8.0

Overall

8.0

Entertainment

7.5

Boarding

8.1

Food

7.0

Crew

8.6

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.

Comfort

8.0

Overall

8.0

Entertainment

7.5

Boarding

8.1

Food

7.0

Crew

8.6

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.

Comfort

8.0

Overall

8.0

Entertainment

7.5

Boarding

8.1

Food

7.0

Crew

8.6

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.

Comfort

8.0

Overall

8.0

Entertainment

7.5

Boarding

8.1

Food

7.0

Crew

8.6

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 8 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 Southwest, Alaska Airlines, and United Airlines fly from Chicago to Portland in about 4h 34m. The time it takes to get you to your destination can typically vary by up to 4h 36m. Airlines will cover a distance of 1733 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 72% 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 $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 (89%), Hawaiian Airlines (78%) and Air Canada (69%).

  • What are the cheapest flights from Chicago to Portland?

    Looking at all options, your cheapest flight can be booked for $133. While the most popular route (Chicago O'Hare Intl - Portland) can be booked for $220 on average, our data indicates $904 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, January is the cheapest month in which you can book a flight from Chicago to Portland (average of $133). 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
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
Pacific City

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 March 31, 2026.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$86Average$178FlexibilityNo cancel feeOn-time65%
Hawaiian AirlinesCheapest$124Average$259FlexibilityNo cancel feeOn-time85%
FrontierCheapest$150Average$232FlexibilityNo cancel feeOn-time62%
Alaska AirlinesCheapest$191Average$310FlexibilityNo cancel feeOn-time75%
United AirlinesCheapest$194Average$343FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$200Average$314FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$227Average$383FlexibilityNo cancel feeOn-time63%

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