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$283+ 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 10/17. Fares are subject to change and may not be available on all flights or dates of travel.
HNL — CHI
Jun 23 — Jun 301
Mon 6/23
Mon 6/30
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 June 18, 2025.

Round-trip from

$561
(Delta)

One-way from

$283
(Alaska Airlines)

Popular in

June

Cheapest in

November

Average price

$882

Good round-trip deal

$811 or less

Good one-way deal

$396 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. 9% potential increase in price ($74 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($17 potential savings vs. average RT price).
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Average for round-trip flights in June 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 June 18, 2025.

This Delta deal was found by Cheapflights users on 6/17. 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 9/44:09 pmHNL - MDW
2 stops15h 19mDelta
Sat 9/69:15 amMDW - HNL
2 stops16h 13mDelta
Deal found 6/17$561
This Delta deal was found by Cheapflights users on 6/17. 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 9/44:09 pmHNL - ORD
2 stops15h 36mDelta
Sat 9/67:45 amORD - HNL
2 stops16h 20mDelta
Deal found 6/17$561
This Alaska Airlines deal was found by Cheapflights users on 6/16. 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 10/29:30 pmHNL - ORD
2 stops19h 34mAlaska Airlines
Mon 10/68:20 amORD - HNL
1 stop12h 25mAlaska Airlines
Deal found 6/16$562
This Southwest deal was found by Cheapflights users on 6/17. 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 10/149:10 pmHNL - MDW
1 stop16h 30mSouthwest
Tue 10/289:35 pmMDW - HNL
1 stop17h 45mSouthwest
Deal found 6/17$573
This American Airlines deal was found by Cheapflights users on 6/15. 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 pmHNL - ORD
Nonstop8h 10mAmerican Airlines
Wed 11/1210:00 amORD - HNL
Nonstop9h 15mAmerican Airlines
Deal found 6/15$652
This Kissandfly.com deal was found by Cheapflights users on 6/17. 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/307:40 amHNL - MDW
2 stops22h 01mMultiple Airlines
Fri 7/46:20 amMDW - HNL
2 stops19h 10mMultiple Airlines
Deal found 6/17$725
This Kissandfly.com deal was found by Cheapflights users on 6/17. 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/303:35 pmHNL - ORD
1 stop16h 03mMultiple Airlines
Fri 7/47:42 amORD - HNL
1 stop17h 48mMultiple Airlines
Deal found 6/17$727
This Hawaiian Airlines deal was found by Cheapflights users on 6/16. 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 Hawaiian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/167:50 amHNL - ORD
1 stop10h 49mHawaiian Airlines
Wed 7/233:09 pmORD - HNL
1 stop13h 25mHawaiian Airlines
Deal found 6/16$774
This United Airlines deal was found by Cheapflights users on 6/16. 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.
Tue 7/81:30 pmHNL - ORD
2 stops17h 22mUnited Airlines
Thu 7/107:40 pmORD - HNL
1 stop23h 24mUnited Airlines
Deal found 6/16$781
This Southwest deal was found by Cheapflights users on 6/17. 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 7/238:10 amHNL - ORD
1 stop10h 30mSouthwest
Thu 7/316:15 amORD - HNL
2 stops17h 15mSouthwest
Deal found 6/17$788

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 June 18, 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 - MDW

HNLMDW

Honolulu

Thu 9/4

4:09 pm-12:28 pm

2 stops15h 19m

Chicago Midway

Sat 9/6

9:15 am-8:28 pm

2 stops16h 13m

$561

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Thu 9/4

4:09 pm-12:45 pm

2 stops15h 36m

Chicago O'Hare Intl

Sat 9/6

7:45 am-7:05 pm

2 stops16h 20m

$561

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Thu 10/2

9:30 pm-10:04 pm

2 stops19h 34m

Chicago O'Hare Intl

Mon 10/6

8:20 am-3:45 pm

1 stop12h 25m

$562

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Tue 10/14

9:10 pm-6:40 pm

1 stop16h 30m

Chicago Midway

Tue 10/28

9:35 pm-10:20 am

1 stop17h 45m

$573

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Thu 11/6

7:00 pm-7:10 am

Nonstop8h 10m

Chicago O'Hare Intl

Wed 11/12

10:00 am-3:15 pm

Nonstop9h 15m

$652

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Mon 6/30

7:40 am-10:41 am

2 stops22h 01m

Chicago Midway

Fri 7/4

6:20 am-8:30 pm

2 stops19h 10m

$725

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Mon 6/30

3:35 pm-12:38 pm

1 stop16h 03m

Chicago O'Hare Intl

Fri 7/4

7:42 am-8:30 pm

1 stop17h 48m

$727

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Wed 7/16

7:50 am-11:39 pm

1 stop10h 49m

Chicago O'Hare Intl

Wed 7/23

3:09 pm-11:34 pm

1 stop13h 25m

$774

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Tue 7/8

1:30 pm-11:52 am

2 stops17h 22m

Chicago O'Hare Intl

Thu 7/10

7:40 pm-2:04 pm

1 stop23h 24m

$781

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Wed 7/23

8:10 am-11:40 pm

1 stop10h 30m

Chicago O'Hare Intl

Thu 7/31

6:15 am-6:30 pm

2 stops17h 15m

$788

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/16

Showing 1-10 of 20 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 June 13, 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 June 18, 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. 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 June 18, 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).

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 June 18, 2025.
Peruse reviews from past customers who have flown with Alaska Airlines, Southwest and Delta from Honolulu to Chicago to help guide your decision. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Crew

8.5

Entertainment

7.1

Overall

8.0

Food

7.1

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Crew

8.5

Entertainment

7.1

Overall

8.0

Food

7.1

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Southwest
8.0
Very good
4,280 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Crew

8.5

Entertainment

7.1

Overall

8.0

Food

7.1

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Delta
8.0
Very good
7,964 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Crew

8.5

Entertainment

7.1

Overall

8.0

Food

7.1

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Hawaiian Airlines
7.8
Good
2,507 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Crew

8.5

Entertainment

7.1

Overall

8.0

Food

7.1

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
United Airlines
7.4
Good
8,810 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Crew

8.5

Entertainment

7.1

Overall

8.0

Food

7.1

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

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.

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

    According to our current data, Delta ($561), Alaska Airlines ($562), and Southwest ($574) offers the cheapest pricing from Honolulu to Chicago. Delta is priced at 20% 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 $283 on Alaska Airlines. Other airlines that offer cheap prices include Southwest from $284 and Hawaiian Airlines from $290 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 (92%), United Airlines (92%) or Air New Zealand (92%) 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 $298. While the most popular route (Honolulu - Chicago O'Hare Intl) can be booked for $465 on average our data indicates $1,101 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 L.A. Live. Hollywood Bowl, Hollywood Walk of Fame, and L.A. Live can be accessed by traveling approximately 12.5 mi, 11.7 mi, and 10.8 mi, respectively from Los Angeles. Those looking to explore during their layover in Los Angeles can rent a car from Los Angeles for about $41 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 Honolulu?

Book flights to Honolulu if you plan to visit one of these locations
Merrillville
Lansing
Benton Harbor
Porter
Hammond
Valparaiso
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 June 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
Hawaiian AirlinesCheapest$280Average$777FlexibilityNo cancel feeOn-time85%
DeltaCheapest$301Average$606FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$422Average$690FlexibilityNo cancel feeOn-time71%
Alaska AirlinesCheapest$461Average$728FlexibilityNo cancel feeOn-time75%
SouthwestCheapest$606Average$783FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$778Average$1,091FlexibilityNo cancel feeOn-time69%

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