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$180+ 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 12/11. Fares are subject to change and may not be available on all flights or dates of travel.
HNL — CHI
Dec 6 — Dec 131
Sat 12/6
Sat 12/13
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 November 6, 2025.

This Alaska Airlines deal was found by Cheapflights users on 11/5. 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 12/252:25 pmKOA - ORD
1 stop29h 34mAlaska Airlines
Mon 2/232:59 pmORD - KOA
1 stop27h 47mAlaska Airlines
Deal found 11/5$383
This Alaska Airlines deal was found by Cheapflights users on 11/5. 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 12/183:52 pmOGG - ORD
1 stop24h 10mAlaska Airlines
Sun 1/48:58 pmORD - OGG
1 stop28h 39mAlaska Airlines
Deal found 11/5$383
This Kiwi.com deal was found by Cheapflights users on 11/6. 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.
Wed 12/178:00 amHNL - ORD
1 stop18h 05mMultiple Airlines
Sat 1/108:48 pmORD - HNL
2 stops42h 23mMultiple Airlines
Deal found 11/6$385
This Alaska Airlines deal was found by Cheapflights users on 11/5. 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.
Mon 12/83:07 pmKOA - ORD
2 stops19h 02mAlaska Airlines
Fri 12/123:05 pmORD - KOA
2 stops25h 50mAlaska Airlines
Deal found 11/5$426
This Kiwi.com deal was found by Cheapflights users on 11/4. 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.
Tue 12/28:00 amHNL - ORD
1 stop18h 25mMultiple Airlines
Tue 12/99:06 pmORD - HNL
2 stops21h 55mMultiple Airlines
Deal found 11/4$444
This Expedia deal was found by Cheapflights users on 11/6. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/179:50 pmHNL - ORD
1 stop11h 26mAlaska Airlines
Sat 1/103:49 pmORD - HNL
1 stop33h 32mAlaska Airlines
Deal found 11/6$448
This Kiwi.com deal was found by Cheapflights users on 11/4. 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 12/54:06 pmHNL - ORD
1 stop28h 07mMultiple Airlines
Wed 12/109:06 pmORD - HNL
2 stops22h 34mMultiple Airlines
Deal found 11/4$455
This Alaska Airlines deal was found by Cheapflights users on 11/6. 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 12/238:13 amHNL - ORD
1 stop31h 49mAlaska Airlines
Mon 1/123:49 pmORD - HNL
1 stop31h 04mAlaska Airlines
Deal found 11/6$459
This Delta deal was found by Cheapflights users on 11/5. 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 12/154:45 pmHNL - MDW
1 stop12h 09mDelta
Thu 1/16:00 amMDW - HNL
1 stop15h 00mDelta
Deal found 11/5$461
This Delta deal was found by Cheapflights users on 11/5. 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 12/154:45 pmHNL - ORD
1 stop13h 15mDelta
Thu 1/16:45 amORD - HNL
1 stop14h 15mDelta
Deal found 11/5$461
This Alaska Airlines deal was found by Cheapflights users on 11/4. 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 12/2311:28 pmHNL - ORD
1 stop16h 34mAlaska Airlines
Mon 1/53:37 pmORD - HNL
1 stop33h 54mAlaska Airlines
Deal found 11/4$462
This Delta deal was found by Cheapflights users on 11/5. 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.
Wed 11/2610:20 pmOGG - ORD
1 stop11h 26mDelta
Sun 11/305:23 amORD - OGG
1 stop14h 05mDelta
Deal found 11/5$464

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 November 6, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$379
(Alaska Airlines)

One-way from

$180
(Kiwi.com)

Popular in

July

Cheapest in

October

Average price

$712

Good round-trip deal

$350 or less

Good one-way deal

$304 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. 12% potential increase in price ($104 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 November 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).
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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 November 6, 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

Thu 12/25

2:25 pm-11:59 pm

1 stop29h 34m

Chicago O'Hare Intl

Mon 2/23

2:59 pm-2:46 pm

1 stop27h 47m

$383

HiloChicago

ITO - ORD

ITOORD

Hilo Intl

Wed 1/21

7:44 pm-5:10 pm

2 stops17h 26m

Chicago O'Hare Intl

Tue 2/3

3:49 pm-5:29 pm

2 stops29h 40m

$415

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Mon 12/8

3:07 pm-2:09 pm

2 stops19h 02m

Chicago O'Hare Intl

Fri 12/12

3:05 pm-12:55 pm

2 stops25h 50m

$426

HiloChicago

ITO - ORD

ITOORD

Hilo Intl

Thu 1/22

6:00 am-11:37 pm

2 stops13h 37m

Chicago O'Hare Intl

Mon 2/2

6:06 pm-4:13 pm

2 stops26h 07m

$439

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Mon 12/15

4:45 pm-8:54 am

1 stop12h 09m

Chicago Midway

Thu 1/1

6:00 am-5:00 pm

1 stop15h 00m

$461

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Mon 12/15

4:45 pm-10:00 am

1 stop13h 15m

Chicago O'Hare Intl

Thu 1/1

6:45 am-5:00 pm

1 stop14h 15m

$461

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Mon 12/22

4:45 pm-9:01 am

1 stop12h 16m

Chicago O'Hare Intl

Thu 1/22

7:30 am-5:07 pm

1 stop13h 37m

$461

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Thu 12/18

10:38 am-6:05 am

2 stops15h 27m

Chicago O'Hare Intl

Sun 1/4

10:49 pm-12:38 pm

1 stop17h 49m

$464

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Wed 11/26

10:20 pm-1:46 pm

1 stop11h 26m

Chicago O'Hare Intl

Sun 11/30

5:23 am-3:28 pm

1 stop14h 05m

$464

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Sun 2/1

9:40 pm-11:37 pm

2 stops21h 57m

Chicago O'Hare Intl

Wed 2/11

9:00 am-9:21 pm

1 stop16h 21m

$465

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/6

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 $220). Flying from Hawaii to Chicago in July is currently the most expensive (average of $658). 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 November 6, 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 November 6, 2025.

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

How much does it cost to fly round-trip from Hawaii to Chicago?

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, Delta, and Southwest can get you from Hawaii to Chicago in just under 11h 05m. Your travel time can differ by up to 18h 29m. Airlines will cover a distance of 4184 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 ($183), Delta ($207), and American Airlines ($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 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 (93%), 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 $1,699, our data shows the cheapest flight currently is $258. When looking at the most popular route, (Honolulu - Chicago O'Hare Intl), you can expect to pay $455 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 $220). Flying from Hawaii to Chicago in July is currently the most expensive (average of $658). 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?

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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 November 6, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$218Average$669FlexibilityNo cancel feeOn-timeN/A
Hawaiian AirlinesCheapest$322Average$743FlexibilityNo cancel feeOn-time85%
United AirlinesCheapest$432Average$837FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$442Average$733FlexibilityNo cancel feeOn-time71%
Alaska AirlinesCheapest$467Average$814FlexibilityNo cancel feeOn-time75%
SouthwestCheapest$516Average$771FlexibilityNo cancel feeOn-time63%

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