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$261+ Cheap flights from Honolulu (HNL) to Chicago (CHI)

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 11/25. Fares are subject to change and may not be available on all flights or dates of travel.
HNL — CHI
Oct 25 — Nov 11
Sat 10/25
Sat 11/1
1 adult, Economy
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Cheapflights Tip: The best prices from Honolulu to Chicago are usually found in November or October, booked 26 days in advance, depart on a Wednesday or Monday and return on a Wednesday

Cheap flight deals from Honolulu to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Honolulu (HNL) to Chicago (CHI). 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 September 25, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$431
(Kiwi.com)

One-way from

$261
(Alaska Airlines)

Popular in

July

Cheapest in

November

Average price

$610

Good round-trip deal

$576 or less

Good one-way deal

$323 or less
Provider with most accurate pricing for Honolulu-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Honolulu-Chicago (CHI) flights.
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From Honolulu to Chicago (CHI)
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One-way flight from Honolulu to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 13% potential increase in price ($111 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($14 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in September 2025
Search Deals
Price to beat on a round-trip flight from Honolulu to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Honolulu to Chicago (CHI).
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Find flight deals from Honolulu to Chicago

Cheapest flights from Honolulu to Chicago
Explore the most affordable flight options available from Honolulu to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 25, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/25. 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 11/1311:04 amHNL - ORD
1 stop33h 39mMultiple Airlines
Sun 11/163:30 pmORD - HNL
1 stop24h 23mMultiple Airlines
Deal found 9/25$431
This flugladen.de deal was found by Cheapflights users on 9/25. 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 flugladen.de is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/273:12 pmHNL - ORD
2 stops28h 00mMultiple Airlines
Mon 11/310:43 pmORD - HNL
1 stop16h 50mMultiple Airlines
Deal found 9/25$464
This Alaska Airlines deal was found by Cheapflights users on 9/23. 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.
Tue 10/147:55 amHNL - ORD
1 stop11h 04mAlaska Airlines
Tue 10/218:20 amORD - HNL
1 stop17h 45mAlaska Airlines
Deal found 9/23$471
This Alaska Airlines deal was found by Cheapflights users on 9/23. 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 11/712:40 pmHNL - ORD
1 stop31h 19mAlaska Airlines
Sun 11/99:20 amORD - HNL
1 stop12h 35mAlaska Airlines
Deal found 9/23$472
This Alaska Airlines deal was found by Cheapflights users on 9/25. 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.
Tue 12/2312:40 pmHNL - ORD
1 stop21h 57mAlaska Airlines
Mon 1/122:59 pmORD - HNL
1 stop25h 36mAlaska Airlines
Deal found 9/25$475
This Kiwi.com deal was found by Cheapflights users on 9/25. 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 11/61:42 pmHNL - ORD
2 stops29h 18mMultiple Airlines
Tue 11/118:30 pmORD - HNL
1 stop19h 03mMultiple Airlines
Deal found 9/25$476
This Alaska Airlines deal was found by Cheapflights users on 9/23. 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.
Tue 10/147:55 amHNL - ORD
1 stop11h 04mAlaska Airlines
Mon 10/207:59 pmORD - HNL
1 stop20h 52mAlaska Airlines
Deal found 9/23$477
This American Airlines deal was found by Cheapflights users on 9/25. 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.
Mon 10/2712:59 pmHNL - ORD
1 stop12h 02mAmerican Airlines
Mon 11/31:49 pmORD - HNL
1 stop12h 13mAmerican Airlines
Deal found 9/25$478
This Southwest deal was found by Cheapflights users on 9/24. 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 10/229:05 pmHNL - MDW
1 stop11h 15mSouthwest
Fri 10/2411:00 amMDW - HNL
1 stop15h 00mSouthwest
Deal found 9/24$479
This Alaska Airlines deal was found by Cheapflights users on 9/25. 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 10/238:00 amHNL - ORD
1 stop10h 59mAlaska Airlines
Mon 10/272:54 pmORD - HNL
1 stop31h 01mAlaska Airlines
Deal found 9/25$479
This Delta deal was found by Cheapflights users on 9/25. 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.
Tue 12/234:45 pmHNL - ORD
1 stop12h 16mDelta
Mon 1/127:00 amORD - HNL
2 stops17h 33mDelta
Deal found 9/25$480
This Delta deal was found by Cheapflights users on 9/23. 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.
Tue 10/2110:31 pmHNL - MDW
2 stops14h 12mDelta
Tue 10/286:00 amMDW - HNL
1 stop12h 32mDelta
Deal found 9/23$484

Cheapflights Fare Finder

 
Customize your flight search to find flights from Honolulu to Chicago 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 September 25, 2025.
Use the filters below to find and compare flights from Honolulu to Chicago that are best for you.

Fly from

Honolulu

Fly to

Chicago

Route

Depart

Return

Price

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Sun 3/1

8:00 am-11:10 pm

1 stop11h 10m

Chicago O'Hare Intl

Tue 3/3

9:00 am-12:25 pm

1 stop31h 25m

$468

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Sun 3/1

8:15 am-11:44 pm

1 stop11h 29m

Chicago O'Hare Intl

Tue 3/3

5:50 am-3:19 pm

1 stop13h 29m

$471

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Fri 11/7

12:40 pm-11:59 pm

1 stop31h 19m

Chicago O'Hare Intl

Sun 11/9

9:20 am-5:55 pm

1 stop12h 35m

$472

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Tue 12/23

8:18 am-11:59 pm

1 stop11h 41m

Chicago O'Hare Intl

Mon 1/12

2:59 pm-12:35 pm

1 stop25h 36m

$475

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Tue 10/14

7:55 am-11:59 pm

1 stop11h 04m

Chicago O'Hare Intl

Mon 10/20

7:59 pm-11:51 am

1 stop20h 52m

$477

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Wed 10/22

9:05 pm-1:20 pm

1 stop11h 15m

Chicago Midway

Fri 10/24

11:00 am-9:00 pm

1 stop15h 00m

$479

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Mon 11/24

8:00 am-1:30 am

1 stop13h 30m

Chicago Midway

Tue 12/2

8:20 am-9:00 pm

1 stop16h 40m

$479

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Sat 11/22

8:00 am-12:40 am

1 stop12h 40m

Chicago Midway

Fri 11/28

11:15 am-9:00 pm

1 stop13h 45m

$479

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Tue 12/23

4:45 pm-9:01 am

1 stop12h 16m

Chicago O'Hare Intl

Mon 1/12

7:00 am-8:33 pm

2 stops17h 33m

$480

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Tue 10/21

10:31 pm-5:43 pm

2 stops14h 12m

Chicago Midway

Tue 10/28

6:00 am-1:32 pm

1 stop12h 32m

$484

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/23

Showing 1-10 of 49 results
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Compare providers for flights from Honolulu to Chicago

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 Honolulu to Chicago in September.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice 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 Honolulu-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Honolulu-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Honolulu-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Honolulu-Chicago 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 Honolulu-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

The best insider tips for Honolulu to Chicago flights

Snippets provided in this section are AI-generated based on a summarization of Cheapflights-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
Cheapflights partnered with top experts to bring you the best recommendations for your Honolulu to Chicago trip
Airports
HNL

Expect up to 1-hour security lines at Terminal 2. Arrive early to ensure smooth departure for your Chicago flight.

Read more about HNLby Yulia Denisyuk
ORD

For a quick city transfer, take the 'L' train from ORD to downtown Chicago, avoiding potential traffic delays.

Read more about ORDby Ramsey Qubein
Our travel experts
Ramsey Qubein

Ramsey Qubein

Expert on ORD

Ramsey Qubein

Ramsey Qubein

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
Yulia Denisyuk

Yulia Denisyuk

Expert on HNL

Yulia Denisyuk

Yulia Denisyuk

Yulia is a freelance journalist who’s dispatched from 90+ countries. Her work focuses on cultures, adventure trips and air travel, appearing in NatGeo, NYT, CNTraveler, and more. For past assignments, she’s stayed with nomads in Mongolia and learned the art of Imigongo in Rwanda. She’s based in Chicago; in winter she often questions that decision.

Read more

Best time to book a flight from Honolulu to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Honolulu 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 Honolulu to Chicago

How far ahead should I book a flight from Honolulu to Chicago?

Use this chart to determine the optimal time to book a round-trip flight from Honolulu to Chicago. Price data was last updated on September 19, 2025.

The price you pay for your flight from Honolulu to Chicago may vary depending on when you book. For the best chance of a lower fare, look to book 26 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

What is the cheapest month to book a flight from Honolulu to Chicago?

Currently, August is the cheapest month in which you can book a flight from Honolulu to Chicago (average of $245). Flying from Honolulu to Chicago in March is currently the most expensive (average of $321). 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 HNL to CHI?

Find hourly flight availability from Honolulu to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 25, 2025.

When flying from Honolulu to Chicago, the time of day you fly usually plays a role in the price. Save by searching for a flight at noon, which can drop the price by up to 34% versus a flight in the evening.

What is the cheapest day to fly from Honolulu to Chicago?

Use this chart to determine the cheapest time to fly round-trip from Honolulu to Chicago. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Honolulu to Chicago flight should consider departing on Wednesday at noon when fares are most often at their lowest. Saturday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Honolulu to Chicago

Explore weekly flight availability from Honolulu to Chicago. 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 September 25, 2025.

The most flights from HNL to CHI are scheduled on a Monday (3 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (3 on average).

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated September 25, 2025.
Read through reviews of airlines operating flights from Honolulu to Chicago, such as Alaska Airlines, Southwest, and Delta. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Crew

8.5

Overall

8.0

Comfort

7.8

Food

7.1

Entertainment

7.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Crew

8.5

Overall

8.0

Comfort

7.8

Food

7.1

Entertainment

7.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.
Southwest
8.0
Very good
4,246 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Crew

8.5

Overall

8.0

Comfort

7.8

Food

7.1

Entertainment

7.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.
Delta
8.0
Very good
7,973 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Crew

8.5

Overall

8.0

Comfort

7.8

Food

7.1

Entertainment

7.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.
United Airlines
7.4
Good
8,926 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Crew

8.5

Overall

8.0

Comfort

7.8

Food

7.1

Entertainment

7.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.
American Airlines
7.2
Good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Crew

8.5

Overall

8.0

Comfort

7.8

Food

7.1

Entertainment

7.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.

Related info for your journey

Find useful and relevant information for your journey from Honolulu to Chicago. 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 Honolulu to Chicago?

    Located just 4.4 mi from the city center, Honolulu is the airport most travelers will use when flying to Chicago from Honolulu. Booking flights from Honolulu (HNL) to Chicago should be relatively easy as there are 3 daily outbound flights to Chicago from 6 different airlines.

  • How long is the flight from Honolulu to Chicago?

    A quick flight from Honolulu to Chicago can take about 11h 10m. Alaska Airlines provides one of the quickest options available for as low as $468. There are 4234 mi between Honolulu and Chicago. This flight may include one or multiple stops.

  • What are the cheapest airlines flying from Honolulu to Chicago round-trip?

    According to our current data, Delta ($231), Hawaiian Airlines ($335), and American Airlines ($442) offers the cheapest pricing from Honolulu to Chicago. Delta is priced at 67% lower than the current average price of a flight leaving 3 months from now.

  • What are the cheapest airlines to fly from Honolulu to Chicago one-way?

    One-way options have recently been found by users for as low as $262 on Southwest. Other airlines that offer cheap prices include Alaska Airlines from $266 and Delta from $277 one-way.

  • What are the most popular routes from Honolulu to Chicago?

    Most travelers choose Honolulu - Chicago O'Hare Intl, Honolulu - Chicago Midway or Honolulu - Chicago Greater Rockford when deciding on the best route from Honolulu to Chicago.

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

    Consider Avianca (97%), United Airlines (97%) or Air New Zealand (97%) when booking your flight. These represent the most reliable airlines when flying from Honolulu to Chicago.

  • What are the cheapest flights from Honolulu to Chicago?

    Looking at all options, your cheapest flight can be booked for $249. While the most popular route (Honolulu - Chicago O'Hare Intl) can be booked for $471 on average, our data indicates $1,731 when flying from Honolulu to Chicago.

  • Where are the most common layover locations when flying from Honolulu to Chicago?

    Flights departing from Honolulu and landing in Chicago layover in Los Angeles most frequently.

  • What are some popular things to do or see while on a layover in Los Angeles?

    If you're on a layover in Los Angeles and looking for things to do, consider visiting Hollywood Bowl, Hollywood Walk of Fame, or Little Tokyo. Hollywood Bowl, Hollywood Walk of Fame, and Little Tokyo can be accessed by traveling approximately 12.5 mi, 11.7 mi, and 12.1 mi, respectively from Los Angeles. Those looking to explore during their layover in Los Angeles can rent a car from Los Angeles for about $39 per day.

  • Where are the least popular layover locations for Honolulu to Chicago flights?

    Flights departing from Honolulu and landing in Chicago layover in Los Angeles least frequently.

  • Can I find deals for flights from Honolulu to Chicago that include hotel bookings?

    Yes. In addition to deals on Honolulu to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Honolulu to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Honolulu to Chicago.

  • Can I find deals for business class flights from Honolulu to Chicago?

    Yes. Cheapflights offers flight deals from Honolulu to Chicago 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 Honolulu to Chicago?

    Currently, August is the cheapest month in which you can book a flight from Honolulu to Chicago (average of $245). Flying from Honolulu to Chicago in March is currently the most expensive (average of $321). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
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Hammond
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Porter
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Top 6 airlines flying from Honolulu to Chicago

Discover the top 6 airlines that operate flights from Honolulu to Chicago. 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 September 25, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$231Average$624FlexibilityNo cancel feeOn-timeN/A
Hawaiian AirlinesCheapest$335Average$770FlexibilityNo cancel feeOn-time85%
American AirlinesCheapest$442Average$753FlexibilityNo cancel feeOn-time71%
Alaska AirlinesCheapest$462Average$767FlexibilityNo cancel feeOn-time75%
SouthwestCheapest$617Average$798FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$781Average$1,083FlexibilityNo cancel feeOn-time69%

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