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$294+ 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 9/10. Fares are subject to change and may not be available on all flights or dates of travel.
HNL — CHI
Aug 19 — Aug 261
Tue 8/19
Tue 8/26
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 Tuesday

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 August 14, 2025.

Round-trip from

$415
(Alaska Airlines)

One-way from

$294
(Alaska Airlines)

Popular in

July

Cheapest in

November

Average price

$678

Good round-trip deal

$699 or less

Good one-way deal

$355 or less
From Honolulu to Chicago (CHI)
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One-way flight from Honolulu to Chicago (CHI)
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Highest demand for flights based on searches. 10% potential increase in price ($86 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($14 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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Price to beat on a round-trip flight from Honolulu to Chicago (CHI).
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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 August 14, 2025.

This Alaska Airlines deal was found by Cheapflights users on 8/12. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/49:00 amHNL - ORD
1 stop24h 54mAlaska Airlines
Tue 11/117:59 pmORD - HNL
1 stop25h 56mAlaska Airlines
Deal found 8/12$415
This Alaska Airlines deal was found by Cheapflights users on 8/14. 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 11/79:00 amHNL - ORD
1 stop24h 54mAlaska Airlines
Wed 11/129:20 amORD - HNL
1 stop16h 32mAlaska Airlines
Deal found 8/14$417
This Alaska Airlines deal was found by Cheapflights users on 8/11. 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.
Tue 11/49:00 amHNL - ORD
1 stop24h 54mAlaska Airlines
Mon 11/109:20 amORD - HNL
1 stop12h 35mAlaska Airlines
Deal found 8/11$419
This Alaska Airlines deal was found by Cheapflights users on 8/14. 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.
Sat 11/89:00 amHNL - ORD
1 stop11h 24mAlaska Airlines
Tue 11/119:20 amORD - HNL
1 stop16h 32mAlaska Airlines
Deal found 8/14$421
This American Airlines deal was found by Cheapflights users on 8/14. 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.
Thu 11/67:00 amHNL - ORD
1 stop12h 59mAmerican Airlines
Mon 11/1011:45 amORD - HNL
1 stop14h 14mAmerican Airlines
Deal found 8/14$423
This Kiwi.com deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/123:05 pmHNL - ORD
1 stop15h 46mMultiple Airlines
Tue 9/1611:15 amORD - HNL
2 stops38h 40mMultiple Airlines
Deal found 8/13$424
This Delta deal was found by Cheapflights users on 8/14. 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.
Fri 11/74:45 pmHNL - MDW
1 stop11h 55mDelta
Tue 11/119:30 amMDW - HNL
2 stops16h 15mDelta
Deal found 8/14$428
This Delta deal was found by Cheapflights users on 8/13. 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 9/301:15 pmHNL - ORD
2 stops14h 10mDelta
Wed 10/297:37 amORD - HNL
1 stop16h 32mDelta
Deal found 8/13$428
This Delta deal was found by Cheapflights users on 8/14. 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.
Thu 9/41:20 pmHNL - ORD
2 stops13h 44mDelta
Sun 9/77:15 amORD - HNL
1 stop12h 04mDelta
Deal found 8/14$429
This Kiwi.com deal was found by Cheapflights users on 8/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/49:49 amHNL - ORD
2 stops21h 10mMultiple Airlines
Mon 9/86:30 amORD - HNL
1 stop19h 01mMultiple Airlines
Deal found 8/12$431
This Delta deal was found by Cheapflights users on 8/13. 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.
Mon 9/291:00 pmHNL - MDW
2 stops14h 53mDelta
Thu 10/309:20 amMDW - HNL
2 stops16h 06mDelta
Deal found 8/13$434
This Delta deal was found by Cheapflights users on 8/12. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/41:20 pmHNL - ORD
2 stops13h 44mDelta
Tue 9/167:55 amORD - HNL
2 stops16h 02mDelta
Deal found 8/12$434

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 August 14, 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

Tue 11/4

9:00 am-1:54 pm

1 stop24h 54m

Chicago O'Hare Intl

Tue 11/11

7:59 pm-5:55 pm

1 stop25h 56m

$415

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Fri 11/7

9:00 am-1:54 pm

1 stop24h 54m

Chicago O'Hare Intl

Wed 11/12

9:20 am-9:52 pm

1 stop16h 32m

$417

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Fri 11/7

12:40 pm-1:54 pm

1 stop21h 14m

Chicago O'Hare Intl

Tue 11/11

7:59 pm-9:52 pm

1 stop29h 53m

$417

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Fri 12/5

8:00 am-1:59 pm

1 stop25h 59m

Chicago O'Hare Intl

Wed 12/10

9:00 am-9:05 pm

1 stop16h 05m

$417

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Fri 11/7

9:00 am-1:54 pm

1 stop24h 54m

Chicago O'Hare Intl

Mon 11/10

9:20 am-5:55 pm

1 stop12h 35m

$419

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Tue 11/4

9:00 am-1:54 pm

1 stop24h 54m

Chicago O'Hare Intl

Mon 11/10

9:20 am-5:55 pm

1 stop12h 35m

$419

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Sat 11/8

9:00 am-12:24 am

1 stop11h 24m

Chicago O'Hare Intl

Wed 11/12

9:20 am-5:55 pm

1 stop12h 35m

$421

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Wed 10/22

7:55 am-11:59 pm

1 stop11h 04m

Chicago O'Hare Intl

Mon 10/27

7:00 am-1:43 pm

1 stop11h 43m

$421

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Sat 11/8

9:00 am-12:24 am

1 stop11h 24m

Chicago O'Hare Intl

Tue 11/11

9:20 am-9:52 pm

1 stop16h 32m

$421

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Thu 12/4

8:00 am-11:10 pm

1 stop11h 10m

Chicago O'Hare Intl

Mon 12/8

7:00 am-2:55 pm

1 stop11h 55m

$423

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/11

Showing 1-10 of 52 results
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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 August 8, 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 August 14, 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 35% 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. Friday evenings flights should be avoided if possible as fares are typically the most expensive at this time.

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 August 14, 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

Crew

8.5

Comfort

7.8

Overall

8.0

Entertainment

7.0

Boarding

8.1

Food

7.1

Reviews

1 / 20
8.0
Excellent

Anonymous,Aug 2025

BOI - LAX

flying in first class, my husband froze the entire flight and was miserable. first class does not offer blankets or any entertainment. (TV etc)
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Comfort

7.8

Overall

8.0

Entertainment

7.0

Boarding

8.1

Food

7.1

Reviews

1 / 20
8.0
Excellent

Anonymous,Aug 2025

BOI - LAX

flying in first class, my husband froze the entire flight and was miserable. first class does not offer blankets or any entertainment. (TV etc)
Southwest
8.0
Very good
4,244 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Comfort

7.8

Overall

8.0

Entertainment

7.0

Boarding

8.1

Food

7.1

Reviews

1 / 20
8.0
Excellent

Anonymous,Aug 2025

BOI - LAX

flying in first class, my husband froze the entire flight and was miserable. first class does not offer blankets or any entertainment. (TV etc)
Delta
8.0
Very good
7,980 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Comfort

7.8

Overall

8.0

Entertainment

7.0

Boarding

8.1

Food

7.1

Reviews

1 / 20
8.0
Excellent

Anonymous,Aug 2025

BOI - LAX

flying in first class, my husband froze the entire flight and was miserable. first class does not offer blankets or any entertainment. (TV etc)
United Airlines
7.4
Good
8,916 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Comfort

7.8

Overall

8.0

Entertainment

7.0

Boarding

8.1

Food

7.1

Reviews

1 / 20
8.0
Excellent

Anonymous,Aug 2025

BOI - LAX

flying in first class, my husband froze the entire flight and was miserable. first class does not offer blankets or any entertainment. (TV etc)
American Airlines
7.2
Good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Comfort

7.8

Overall

8.0

Entertainment

7.0

Boarding

8.1

Food

7.1

Reviews

1 / 20
8.0
Excellent

Anonymous,Aug 2025

BOI - LAX

flying in first class, my husband froze the entire flight and was miserable. first class does not offer blankets or any entertainment. (TV etc)

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 2 daily outbound flights to Chicago from 6 different airlines.

  • 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 ($431) 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 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 $225. While the most popular route (Honolulu - Chicago O'Hare Intl) can be booked for $419 on average our data indicates $1,717 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 The Wiltern. Hollywood Bowl, Hollywood Walk of Fame, and The Wiltern can be accessed by traveling approximately 12.5 mi, 11.7 mi, and 10.0 mi, respectively from Los Angeles. Those looking to explore during their layover in Los Angeles can rent a car from Los Angeles for about $52 per day.

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

    Flights departing from Honolulu and landing in Chicago layover in Seattle 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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Lansing
Hammond
Benton Harbor
Porter
Chesterton

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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 August 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$231Average$620FlexibilityNo cancel feeOn-timeN/A
Hawaiian AirlinesCheapest$335Average$777FlexibilityNo cancel feeOn-time85%
American AirlinesCheapest$431Average$746FlexibilityNo cancel feeOn-time71%
Alaska AirlinesCheapest$457Average$744FlexibilityNo cancel feeOn-time75%
SouthwestCheapest$606Average$788FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$784Average$1,081FlexibilityNo cancel feeOn-time69%

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