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$181+ 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 1/15. Fares are subject to change and may not be available on all flights or dates of travel.
HNL — CHI
Dec 31 — Jan 71
Wed 12/31
Wed 1/7
1 adult, Economy
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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 December 1, 2025.

This Delta deal was found by Cheapflights users on 11/30. 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 12/259:20 pmLIH - ORD
1 stop12h 00mDelta
Wed 1/72:20 pmORD - LIH
2 stops32h 01mDelta
Deal found 11/30$398
This Alaska Airlines deal was found by Cheapflights users on 11/30. 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 12/2511:59 amLIH - ORD
1 stop13h 03mAlaska Airlines
Tue 1/68:39 amORD - LIH
1 stop32h 24mAlaska Airlines
Deal found 11/30$403
This Alaska Airlines deal was found by Cheapflights users on 11/30. 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 12/2511:59 amLIH - ORD
1 stop13h 03mAlaska Airlines
Wed 1/79:00 amORD - LIH
1 stop32h 03mAlaska Airlines
Deal found 11/30$423
This Alaska Airlines deal was found by Cheapflights users on 12/1. 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 12/2412:40 pmHNL - ORD
1 stop27h 22mAlaska Airlines
Sun 1/119:00 amORD - HNL
1 stop31h 48mAlaska Airlines
Deal found 12/1$451
This Alaska Airlines deal was found by Cheapflights users on 12/1. 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 stop27h 22mAlaska Airlines
Mon 1/129:00 amORD - HNL
1 stop13h 53mAlaska Airlines
Deal found 12/1$452
This American Airlines deal was found by Cheapflights users on 11/30. 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.
Fri 12/510:44 pmLIH - ORD
1 stop11h 28mAmerican Airlines
Fri 1/97:05 amORD - LIH
1 stop12h 50mAmerican Airlines
Deal found 11/30$453
This Delta deal was found by Cheapflights users on 11/30. 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 12/59:50 pmLIH - ORD
2 stops15h 07mDelta
Fri 1/96:50 amORD - LIH
2 stops17h 05mDelta
Deal found 11/30$454
This Alaska Airlines deal was found by Cheapflights users on 11/30. 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 12/59:00 pmLIH - ORD
2 stops13h 39mAlaska Airlines
Fri 1/96:06 pmORD - LIH
1 stop32h 35mAlaska Airlines
Deal found 11/30$458
This Delta deal was found by Cheapflights users on 11/30. 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 12/269:20 pmLIH - ORD
1 stop22h 39mDelta
Wed 1/72:20 pmORD - LIH
2 stops32h 01mDelta
Deal found 11/30$459
This Alaska Airlines deal was found by Cheapflights users on 11/30. 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 12/2511:59 amLIH - ORD
1 stop13h 03mAlaska Airlines
Mon 1/58:58 pmORD - LIH
1 stop22h 47mAlaska Airlines
Deal found 11/30$464
This Delta deal was found by Cheapflights users on 11/30. 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 12/510:55 pmLIH - MDW
2 stops15h 23mDelta
Fri 1/99:32 amMDW - LIH
2 stops14h 23mDelta
Deal found 11/30$474
This Delta deal was found by Cheapflights users on 11/30. 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 12/238:10 amHNL - ORD
1 stop11h 49mDelta
Mon 1/127:30 amORD - HNL
1 stop14h 57mDelta
Deal found 11/30$494

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 December 1, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$343
(Alaska Airlines)

One-way from

$181
(Alaska Airlines)

Popular in

July

Cheapest in

September

Average price

$741

Good round-trip deal

$554 or less

Good one-way deal

$300 or less
Provider with most accurate pricing for Honolulu-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Honolulu-Chicago (CHI) flights.
Search Deals
From Hawaii to Chicago (CHI)
Search Deals
One-way flight from Hawaii to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 10% potential increase in price ($83 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($12 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals
Price to beat on a round-trip flight from Hawaii to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Hawaii to Chicago (CHI).
Search Deals

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 December 1, 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

LihueChicago

LIH - ORD

LIHORD

Lihue

Mon 3/2

2:56 pm-2:58 pm

1 stop20h 02m

Chicago O'Hare Intl

Wed 3/4

8:20 am-12:47 pm

1 stop32h 27m

$343

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Mon 3/2

11:54 pm-2:58 pm

1 stop11h 04m

Chicago O'Hare Intl

Wed 3/4

3:07 pm-11:46 pm

1 stop12h 39m

$343

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Mon 3/2

9:09 pm-2:58 pm

2 stops13h 49m

Chicago O'Hare Intl

Wed 3/4

8:20 am-11:46 pm

1 stop19h 26m

$369

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Thu 1/29

9:10 pm-5:10 pm

1 stop16h 00m

Chicago O'Hare Intl

Mon 2/2

8:00 am-9:30 pm

1 stop17h 30m

$382

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Tue 2/10

2:51 pm-2:29 pm

1 stop19h 38m

Chicago O'Hare Intl

Tue 2/17

3:07 pm-3:53 pm

1 stop28h 46m

$392

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Tue 2/10

2:51 pm-2:29 pm

1 stop19h 38m

Chicago O'Hare Intl

Wed 2/18

3:07 pm-3:53 pm

1 stop28h 46m

$392

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Mon 2/9

2:24 pm-2:29 pm

1 stop20h 05m

Chicago O'Hare Intl

Tue 2/17

3:07 pm-3:53 pm

1 stop28h 46m

$392

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Mon 2/9

2:24 pm-2:29 pm

1 stop20h 05m

Chicago O'Hare Intl

Wed 2/18

3:07 pm-3:53 pm

1 stop28h 46m

$392

HiloChicago

ITO - ORD

ITOORD

Hilo Intl

Tue 3/3

6:00 am-11:59 pm

2 stops13h 59m

Chicago O'Hare Intl

Wed 3/4

3:07 pm-5:29 pm

2 stops30h 22m

$394

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Fri 1/16

11:59 pm-11:37 pm

1 stop19h 38m

Chicago O'Hare Intl

Tue 1/20

9:00 am-6:17 am

2 stops25h 17m

$396

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/1

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, November is the cheapest month in which you can book a flight from Hawaii to Chicago (average of $222). Flying from Hawaii to Chicago in July is currently the most expensive (average of $661). 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 December 1, 2025.

One of the essential ways to save on airfare from Hawaii to Chicago is to remain as flexible as possible. Flights that are in the afternoon tend to be the most expensive. A flight in the morning could potentially save you up to 39% on airfare.

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

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

Travelers seeking maximum savings on their Hawaii to Chicago flight should consider departing on Friday mornings 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 Hawaii to Chicago

Explore weekly flight availability from Hawaii 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 December 1, 2025.

The most flights from USHI to CHI are scheduled on a Monday (6 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (2 on average).

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.

  • How long is the flight from Hawaii to Chicago?

    Alaska Airlines, Hawaiian Airlines, and Delta can get you from Hawaii to Chicago in just under 11h 04m. Your travel time can differ by up to 8h 58m. Airlines will cover a distance of 4175 mi. This flight may include one or multiple stops.

  • 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 ($181), Southwest ($211), and Delta ($212).

  • 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 Lihue - 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 (95%), United Airlines (92%), Air New Zealand (92%).

  • What are the cheapest flights from Hawaii to Chicago?

    While on average a flight from Hawaii to Chicago is generally $1,709, our data shows the cheapest flight currently is $197. When looking at the most popular route, (Honolulu - Chicago O'Hare Intl), you can expect to pay $405 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, November is the cheapest month in which you can book a flight from Hawaii to Chicago (average of $222). Flying from Hawaii to Chicago in July is currently the most expensive (average of $661). 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
Lansing
Hammond
Porter
Benton Harbor
Merrillville

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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 December 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$305Average$620FlexibilityNo cancel feeOn-timeN/A
Hawaiian AirlinesCheapest$322Average$743FlexibilityNo cancel feeOn-time85%
United AirlinesCheapest$432Average$852FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$455Average$746FlexibilityNo cancel feeOn-time71%
Alaska AirlinesCheapest$467Average$795FlexibilityNo cancel feeOn-time75%
SouthwestCheapest$581Average$775FlexibilityNo cancel feeOn-time63%

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