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O'Hare Intl

$99+ Cheap flights from Portland (PDX) to O'Hare Intl (ORD)

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 5/19. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — ORD
Mar 24 — Mar 311
Tue 3/24
Tue 3/31
1 adult, Economy
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Find cheap flights from Portland to O'Hare Intl 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 Portland to Chicago O'Hare Intl are usually found in August or September, booked 88 days in advance, depart on a Friday or Wednesday and return on a Tuesday

Cheap flight deals from Portland to O'Hare Intl

Cheapest flights from Portland to O'Hare Intl
Explore the most affordable flight options available from Portland to O'Hare Intl. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 22, 2026.

This Kiwi.com deal was found by Cheapflights users on 2/21. 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 3/1612:04 pm
PDX
-
ORD
1 stop10h 53m
Frontier
Thu 3/1910:53 am
ORD
-
PDX
1 stop26h 16m
Frontier
Deal found 2/21$217
This United Airlines deal was found by Cheapflights users on 2/22. 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 3/141:39 pm
PDX
-
ORD
1 stop9h 20m
United Airlines
Sat 3/218:04 pm
ORD
-
PDX
Nonstop4h 41m
United Airlines
Deal found 2/22$218
This Kiwi.com deal was found by Cheapflights users on 2/18. 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.
Tue 3/319:43 am
PDX
-
ORD
2 stops17h 06m
Multiple Airlines
Sat 4/43:35 pm
ORD
-
PDX
1 stop29h 16m
Multiple Airlines
Deal found 2/18$219
This CheapOair deal was found by Cheapflights users on 2/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/232:54 pm
PDX
-
ORD
1 stop12h 56m
Frontier
Sun 4/267:21 pm
ORD
-
PDX
1 stop18h 29m
Frontier
Deal found 2/22$222
This Kiwi.com deal was found by Cheapflights users on 2/18. 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 4/1611:48 am
PDX
-
ORD
1 stop20h 02m
Frontier
Sun 4/198:58 pm
ORD
-
PDX
1 stop14h 01m
Frontier
Deal found 2/18$223
This Expedia deal was found by Cheapflights users on 2/19. 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.
Tue 3/311:35 pm
PDX
-
ORD
1 stop8h 24m
Multiple Airlines
Wed 4/158:58 pm
ORD
-
PDX
1 stop14h 01m
Multiple Airlines
Deal found 2/19$226
This Kiwi.com deal was found by Cheapflights users on 2/18. 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 5/412:45 pm
PDX
-
ORD
1 stop16h 02m
Frontier
Fri 5/89:18 pm
ORD
-
PDX
2 stops40h 39m
Frontier
Deal found 2/18$229
This American Airlines deal was found by Cheapflights users on 2/18. 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 3/3111:59 pm
PDX
-
ORD
Nonstop3h 57m
American Airlines
Tue 4/78:05 pm
ORD
-
PDX
Nonstop4h 37m
American Airlines
Deal found 2/18$231
This Kiwi.com deal was found by Cheapflights users on 2/18. 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 3/3012:04 pm
PDX
-
ORD
1 stop10h 53m
Multiple Airlines
Sat 4/45:53 pm
ORD
-
PDX
2 stops26h 58m
Multiple Airlines
Deal found 2/18$232
This Kiwi.com deal was found by Cheapflights users on 2/19. 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.
Tue 4/2112:38 pm
PDX
-
ORD
2 stops29h 41m
Multiple Airlines
Thu 4/308:52 pm
ORD
-
PDX
1 stop14h 07m
Multiple Airlines
Deal found 2/19$234
This Kiwi.com deal was found by Cheapflights users on 2/18. 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 3/3012:04 pm
PDX
-
ORD
1 stop10h 53m
Multiple Airlines
Sun 4/57:55 am
ORD
-
PDX
1 stop12h 56m
Multiple Airlines
Deal found 2/18$236

Find flight deals from Portland to O'Hare Intl

Discover tips and strategies to find the most affordable flight options for your journey from Portland (PDX) to O'Hare Intl (ORD). 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 22, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$217
(Kiwi.com)

One-way from

$99
(Kiwi.com)

Popular in

March

Cheapest in

August

Average price

$317

Good round-trip deal

$328 or less

Good one-way deal

$168 or less
Provider with most accurate pricing for Portland-Chicago O'Hare Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Portland-Chicago O'Hare Intl flights.
Search Deals
From Portland to Chicago O'Hare Intl
Search Deals
One-way flight from Portland to Chicago O'Hare Intl
Search Deals
Highest demand for flights based on searches. 4% potential increase in price ($15 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 Portland to Chicago O'Hare Intl.
Search Deals
Price to beat on a one-way flight from Portland to Chicago O'Hare Intl.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Portland to O'Hare Intl 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 22, 2026.
Use the filters below to find and compare flights from Portland to Chicago O'Hare Intl Airport that are best for you.

Fly from

Portland

Fly to

O'Hare Intl

Route

Depart

Return

Price

PortlandChicago

PDX - ORD

PDXORD

Portland

Wed 5/6

2:21 pm-8:23 pm

Nonstop4h 02m

Chicago O'Hare Intl

Sat 5/9

7:55 pm-10:30 pm

Nonstop4h 35m

$231

PortlandChicago

PDX - ORD

PDXORD

Portland

Wed 4/1

1:35 pm-11:59 pm

1 stop8h 24m

Chicago O'Hare Intl

Sat 4/4

2:09 pm-4:50 pm

Nonstop4h 41m

$248

PortlandChicago

PDX - ORD

PDXORD

Portland

Wed 6/10

10:40 pm-4:45 am

Nonstop4h 05m

Chicago O'Hare Intl

Sun 6/14

7:05 am-9:39 am

Nonstop4h 34m

$256

PortlandChicago

PDX - ORD

PDXORD

Portland

Mon 4/20

3:30 pm-1:28 am

1 stop7h 58m

Chicago O'Hare Intl

Tue 4/21

4:05 pm-6:34 pm

Nonstop4h 29m

$259

PortlandChicago

PDX - ORD

PDXORD

Portland

Wed 4/1

7:03 am-1:13 pm

Nonstop4h 10m

Chicago O'Hare Intl

Thu 4/2

2:09 pm-4:50 pm

Nonstop4h 41m

$266

PortlandChicago

PDX - ORD

PDXORD

Portland

Fri 7/3

4:10 pm-12:44 am

1 stop6h 34m

Chicago O'Hare Intl

Tue 7/7

7:05 am-9:39 am

Nonstop4h 34m

$266

PortlandChicago

PDX - ORD

PDXORD

Portland

Mon 3/30

4:15 pm-12:29 am

1 stop6h 14m

Chicago O'Hare Intl

Sat 4/4

7:55 pm-10:29 pm

Nonstop4h 34m

$266

PortlandChicago

PDX - ORD

PDXORD

Portland

Tue 3/31

11:15 pm-9:10 am

1 stop7h 55m

Chicago O'Hare Intl

Sun 4/5

1:57 pm-9:53 pm

1 stop9h 56m

$269

PortlandChicago

PDX - ORD

PDXORD

Portland

Thu 5/7

4:15 pm-12:58 am

1 stop6h 43m

Chicago O'Hare Intl

Sun 5/10

9:20 pm-11:55 pm

Nonstop4h 35m

$277

PortlandChicago

PDX - ORD

PDXORD

Portland

Fri 5/15

7:45 pm-6:20 am

1 stop8h 35m

Chicago O'Hare Intl

Mon 5/18

9:20 pm-11:55 pm

Nonstop4h 35m

$277

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/20

Showing 1-10 of 23 results
1
2
3

Compare providers for flights from Portland to O'Hare Intl

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 Portland to O'Hare Intl in February.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
JustAirTicketPrice Accuracy-Trust Score*1 star
CheapflightsfaresPrice Accuracy2 starsTrust Score*2 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
Justfly.comPrice Accuracy3 starsTrust Score*3 stars
CheapOairPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice Accuracy1 starTrust Score*3 stars
Kiwi.comPrice Accuracy3 starsTrust 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 Portland-Chicago O'Hare Intl Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Portland-Chicago O'Hare Intl Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Portland-Chicago O'Hare Intl Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Portland-Chicago O'Hare Intl Airport 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 Portland-Chicago O'Hare Intl Airport 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 Portland to O'Hare Intl

Have a flexible travel schedule? Discover the best time to fly to O'Hare Intl from Portland 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 Portland to Chicago O'Hare Intl Airport

How far ahead should I book a flight from Portland to Chicago O'Hare Intl Airport?

Use this chart to determine the optimal time to book a round-trip flight from Portland to O'Hare Intl. Price data was last updated on February 20, 2026.

Booking 88 days in advance of your planned departure date is, on average, the best time to get cheap flights from Portland to Chicago O'Hare Intl Airport. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

What is the cheapest month to book a flight from Portland to Chicago O'Hare Intl Airport?

Currently, August is the cheapest month in which you can book a flight from Portland to Chicago O'Hare Intl Airport (average of $118). Flying from Portland to Chicago O'Hare Intl Airport in July is currently the most expensive (average of $238). 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 PDX to ORD?

Find hourly flight availability from Portland to O'Hare Intl. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated February 22, 2026.

When flying from Portland to Chicago O'Hare Intl Airport, the time of day you fly usually plays a role in the price. Save by searching for a flight in the afternoon, which can drop the price by up to 36% versus a flight in the morning.

What is the cheapest day to fly from Portland to Chicago O'Hare Intl Airport?

Use this chart to determine the cheapest time to fly round-trip from Portland to O'Hare Intl. Price data was last updated on February 21, 2026.

Travelers seeking maximum savings on their Portland to Chicago O'Hare Intl Airport flight should consider departing on Wednesday 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.

The best insider tips for Portland to Chicago O'Hare Intl Airport 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 Portland to Chicago O'Hare Intl Airport trip
Our travel experts
Harriet Baskas

Harriet Baskas

Expert on United Airlines

Harriet is an award-winning journalist who is happiest in an airport or an unusual museum. Her stories about airports, air travel, and the business of travel have appeared on NBC News, CNBC, USA TODAY, The Points Guy and other outlets. She is the creator of the StuckatTheAirport.com blog and the author of nine books. When not out on the road or exploring the latest airport amenities, she’s home in Seattle getting ready for the next adventure.

Read more
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

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 O'Hare Intl

Get insights into the airlines that provide service to O'Hare Intl. 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 O'Hare Intl. Reviews last updated February 22, 2026.
Get a feel of what it's like to fly with Alaska Airlines, Delta, and Hawaiian Airlines from Portland to Chicago O'Hare Intl Airport by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
11,928 reviews

Entertainment

7.0

Boarding

8.1

Overall

8.0

Comfort

7.8

Crew

8.5

Food

7.1

Reviews

1 / 20
10.0
Excellent

robert,Feb 2026

LAS - SAN

The good customer service team made you fell welcome on the flight.
Alaska Airlines
8.0
Very good
11,928 reviews
Alaska Airlines
8.0
Very good
11,928 reviews

Entertainment

7.0

Boarding

8.1

Overall

8.0

Comfort

7.8

Crew

8.5

Food

7.1

Reviews

1 / 20
10.0
Excellent

robert,Feb 2026

LAS - SAN

The good customer service team made you fell welcome on the flight.
Delta
7.9
Good
8,240 reviews
Alaska Airlines
8.0
Very good
11,928 reviews

Entertainment

7.0

Boarding

8.1

Overall

8.0

Comfort

7.8

Crew

8.5

Food

7.1

Reviews

1 / 20
10.0
Excellent

robert,Feb 2026

LAS - SAN

The good customer service team made you fell welcome on the flight.
Hawaiian Airlines
7.8
Good
2,835 reviews
Alaska Airlines
8.0
Very good
11,928 reviews

Entertainment

7.0

Boarding

8.1

Overall

8.0

Comfort

7.8

Crew

8.5

Food

7.1

Reviews

1 / 20
10.0
Excellent

robert,Feb 2026

LAS - SAN

The good customer service team made you fell welcome on the flight.
United Airlines
7.4
Good
9,341 reviews
Alaska Airlines
8.0
Very good
11,928 reviews

Entertainment

7.0

Boarding

8.1

Overall

8.0

Comfort

7.8

Crew

8.5

Food

7.1

Reviews

1 / 20
10.0
Excellent

robert,Feb 2026

LAS - SAN

The good customer service team made you fell welcome on the flight.
American Airlines
7.2
Good
11,338 reviews
Alaska Airlines
8.0
Very good
11,928 reviews

Entertainment

7.0

Boarding

8.1

Overall

8.0

Comfort

7.8

Crew

8.5

Food

7.1

Reviews

1 / 20
10.0
Excellent

robert,Feb 2026

LAS - SAN

The good customer service team made you fell welcome on the flight.

Related info for your journey

Find useful and relevant information for your journey from Portland to O'Hare Intl. 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 from for flights from Portland to Chicago O'Hare Intl?

    For a flight from Portland to Chicago O'Hare Intl, you will be flying from Portland. Portland (PDX) is just 6.0 mi from the center of the city. Portland is the only Portland airport and it handles 13 outbound flights to Chicago O'Hare Intl per day. 7 airlines have flights to Chicago O'Hare Intl from Portland on a regular basis.

  • How long is the flight from Portland to Chicago O'Hare Intl Airport?

    A quick flight from Portland to Chicago O'Hare Intl Airport can take about 4h 02m. United Airlines provides one of the quickest options available for as low as $231. The distance from Portland to Chicago O'Hare Intl Airport is about 1733 mi. This flight may include one or multiple stops.

  • What are the cheapest airlines flying from Portland to Chicago O'Hare Intl Airport round-trip?

    Our cheapest airline available from Portland to Chicago O'Hare Intl Airport is Frontier. Our recent data shows that you can find tickets from as low as $86 on this airline. Additional options worth looking into are Spirit Airlines and Delta, starting at $93 and $99 round-trip. Frontier is currently priced 75% below the average price you’ll pay for this route.

  • What are the cheapest airlines to fly from Portland to Chicago O'Hare Intl Airport one-way?

    One-way options have recently been found by users for as low as $72 on Frontier. Other airlines that offer cheap prices include Spirit Airlines from $82 and Hawaiian Airlines from $98 one-way.

  • What are the most reliable airlines from Portland to Chicago O'Hare Intl Airport?

    No one likes to see their flight delayed. When booking a flight from Portland to Chicago O'Hare Intl Airport consider choosing Gulf Air (100%), Brussels Airlines (95%) or Lufthansa (90%) as they are the most reliable in getting you off to your destination on time.

  • What are the cheapest flights from Portland to Chicago O'Hare Intl Airport?

    The cheapest flight price from Portland to Chicago O'Hare Intl Airport is $111. On average you can expect to pay $925. The most popular route, (Portland - Chicago O'Hare Intl), can usually be booked for $183.

  • Can I find deals for flights from Portland to O'Hare Intl that include hotel bookings?

    Yes. In addition to deals on Portland to O'Hare Intl flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Portland to O'Hare Intl?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Portland to O'Hare Intl.

  • Can I find deals for business class flights from Portland to O'Hare Intl?

    Yes. Cheapflights offers flight deals from Portland to O'Hare Intl 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 Portland to Chicago O'Hare Intl Airport?

    Currently, August is the cheapest month in which you can book a flight from Portland to Chicago O'Hare Intl Airport (average of $118). Flying from Portland to Chicago O'Hare Intl Airport in July is currently the most expensive (average of $238). 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 O'Hare Intl Airport?

Book flights to Chicago O'Hare Intl Airport if you plan to visit one of these locations
Schaumburg
Rosemont
Gurnee
Naperville
Hoffman Estates
Beloit
Delavan
Des Plaines
Elgin
Downers Grove
Elk Grove Village
Skokie
Oak Brook
South Holland
Libertyville
Oakbrook Terrace
Lake Geneva
Waukegan
Bridgeview
Kenosha

Browse thousands of different options on Cheapflights for your next trip

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Top 7 airlines flying from Portland to O'Hare Intl

Discover the top 7 airlines that operate flights from Portland to O'Hare Intl. 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 22, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$86Average$234FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$93Average$194FlexibilityNo cancel feeOn-time65%
DeltaCheapest$99Average$288FlexibilityNo cancel feeOn-timeN/A
Hawaiian AirlinesCheapest$125Average$278FlexibilityNo cancel feeOn-time85%
American AirlinesCheapest$192Average$313FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$199Average$374FlexibilityNo cancel feeOn-time69%
Alaska AirlinesCheapest$209Average$345FlexibilityNo cancel feeOn-time75%

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