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$203+ Cheap flights from Hawaii 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 10/30. 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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Cheap flight deals from Hawaii to Chicago

Keep the following information in mind while searching for Hawaii to Chicago flight deals. Data was last updated August 14, 2025.

Round-trip from

$409
(Alaska Airlines)

One-way from

$203
(Alaska Airlines)

Popular in

July

Cheapest in

November

Average price

$678

Good round-trip deal

$699 or less

Good one-way deal

$306 or less
From Hawaii to Chicago (CHI)
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One-way flight from Hawaii 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 Hawaii to Chicago (CHI).
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Price to beat on a one-way flight from Hawaii to Chicago (CHI).
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Find flight deals from Hawaii to Chicago

Cheapest flights from Hawaii to Chicago
Explore the most affordable flight options available from Hawaii to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 14, 2025.

This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/49:55 pmKOA - ORD
1 stop13h 03mAmerican Airlines
Sun 9/76:00 amORD - KOA
1 stop12h 42mAmerican Airlines
Deal found 8/12$409
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.
Wed 11/122:46 pmOGG - ORD
1 stop11h 57mAmerican Airlines
Sun 11/165:18 amORD - OGG
1 stop14h 02mAmerican Airlines
Deal found 8/14$409
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.
Wed 11/127:21 amOGG - ORD
2 stops13h 03mAlaska Airlines
Sun 11/169:20 amORD - OGG
1 stop17h 30mAlaska Airlines
Deal found 8/14$414
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.
Fri 10/38:00 amOGG - ORD
1 stop11h 03mAlaska Airlines
Tue 10/147:59 pmORD - OGG
1 stop31h 06mAlaska Airlines
Deal found 8/14$420
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 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.
Thu 9/412:16 pmKOA - ORD
1 stop11h 44mAlaska Airlines
Sun 9/77:00 amORD - KOA
2 stops15h 43mAlaska Airlines
Deal found 8/12$422
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 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.
Wed 10/1511:57 amKOA - ORD
1 stop12h 04mAlaska Airlines
Wed 10/223:50 pmORD - KOA
1 stop25h 39mAlaska Airlines
Deal found 8/12$427

Cheapflights Fare Finder

 
Customize your flight search to find flights from Hawaii 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 Hawaii to Chicago that are best for you.

Fly from

Hawaii

Fly to

Chicago

Route

Depart

Return

Price

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Wed 9/24

8:00 am-12:03 am

1 stop11h 03m

Chicago O'Hare Intl

Mon 9/29

6:20 am-4:44 pm

1 stop15h 24m

$409

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Thu 9/4

9:55 pm-3:58 pm

1 stop13h 03m

Chicago O'Hare Intl

Sun 9/7

6:00 am-1:42 pm

1 stop12h 42m

$409

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Wed 11/12

2:46 pm-6:43 am

1 stop11h 57m

Chicago O'Hare Intl

Sun 11/16

5:18 am-3:20 pm

1 stop14h 02m

$409

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Thu 11/13

11:59 pm-1:54 pm

1 stop9h 55m

Chicago O'Hare Intl

Sun 11/16

6:00 am-2:12 pm

1 stop12h 12m

$409

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Wed 11/12

7:21 am-12:24 am

2 stops13h 03m

Chicago O'Hare Intl

Sun 11/16

9:20 am-10:50 pm

1 stop17h 30m

$414

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

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/13

Showing 1-10 of 60 results
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Best time to book a flight from Hawaii to Chicago

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

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

Currently, August is the cheapest month in which you can book a flight from Hawaii to Chicago (average of $245). Flying from Hawaii 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 HI to CHI?

Find hourly flight availability from Hawaii 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 Hawaii to Chicago, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Related info for your journey

Find useful and relevant information for your journey from Hawaii to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

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

    The cheapest airlines for a one-way flight from Hawaii to Chicago are Alaska Airlines ($203), American Airlines ($205), and Delta ($217).

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

    When deciding which route to take from Hawaii to Chicago consider Honolulu - Chicago O'Hare Intl, Honolulu - Chicago Midway or Kahului - Chicago O'Hare Intl as they are the most popular.

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

    Looking for the most reliable airlines to get you to your destination on time? Our data shows these are most likely to get you from Hawaii to Chicago on time: Avianca (97%), United Airlines (97%), Air New Zealand (97%).

  • What are the cheapest flights from Hawaii to Chicago?

    While on average a flight from Hawaii to Chicago is generally $1,717, our data shows the cheapest flight currently is $225. When looking at the most popular route, (Honolulu - Chicago O'Hare Intl), you can expect to pay $419 for that flight.

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

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

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

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

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

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

    Currently, August is the cheapest month in which you can book a flight from Hawaii to Chicago (average of $245). Flying from Hawaii 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
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

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Alternative routes for Hawaii to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
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Top 6 airlines flying from Hawaii to Chicago

Discover the top 6 airlines that operate flights from Hawaii 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$322Average$746FlexibilityNo cancel feeOn-time85%
American AirlinesCheapest$349Average$610FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$429Average$840FlexibilityNo cancel feeOn-time69%
Alaska AirlinesCheapest$457Average$763FlexibilityNo cancel feeOn-time75%
SouthwestCheapest$606Average$781FlexibilityNo cancel feeOn-time63%

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