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$182+ 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 1/21. Fares are subject to change and may not be available on all flights or dates of travel.
HNL — CHI
Dec 17 — Dec 241
Wed 12/17
Wed 12/24
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 17, 2025.

This Kiwi.com deal was found by Cheapflights users on 11/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/112:25 pmHNL - ORD
2 stops35h 40mMultiple Airlines
Wed 12/317:44 pmORD - HNL
1 stop33h 04mMultiple Airlines
Deal found 11/16$401
This Kiwi.com deal was found by Cheapflights users on 11/15. 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 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
Wed 12/317:44 pmORD - HNL
1 stop33h 04mMultiple Airlines
Deal found 11/15$404
This Kiwi.com deal was found by Cheapflights users on 11/16. 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 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
Sun 1/410:49 pmORD - HNL
2 stops26h 22mMultiple Airlines
Deal found 11/16$420
This Kiwi.com deal was found by Cheapflights users on 11/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/138:00 amHNL - ORD
1 stop12h 13mMultiple Airlines
Wed 12/317:44 pmORD - HNL
1 stop33h 04mMultiple Airlines
Deal found 11/15$425
This Kiwi.com deal was found by Cheapflights users on 11/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/238:00 amHNL - ORD
2 stops36h 12mMultiple Airlines
Tue 1/67:44 pmORD - HNL
1 stop19h 27mMultiple Airlines
Deal found 11/16$430
This Kiwi.com deal was found by Cheapflights users on 11/16. 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 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
Mon 1/57:44 pmORD - HNL
2 stops22h 35mMultiple Airlines
Deal found 11/16$435
This Kiwi.com deal was found by Cheapflights users on 11/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/122:11 pmHNL - ORD
1 stop11h 54mMultiple Airlines
Wed 12/317:44 pmORD - HNL
1 stop33h 04mMultiple Airlines
Deal found 11/15$437
This Kiwi.com deal was found by Cheapflights users on 11/16. 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 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
Thu 1/810:32 pmORD - HNL
2 stops26h 19mMultiple Airlines
Deal found 11/16$440
This Delta deal was found by Cheapflights users on 11/17. 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.
Wed 12/249:55 pmKOA - ORD
1 stop11h 25mDelta
Thu 1/17:25 amORD - KOA
1 stop12h 23mDelta
Deal found 11/17$443
This Kiwi.com deal was found by Cheapflights users on 11/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/168:00 amHNL - ORD
1 stop18h 05mMultiple Airlines
Wed 12/316:05 amORD - HNL
2 stops22h 43mMultiple Airlines
Deal found 11/15$446
This Kiwi.com deal was found by Cheapflights users on 11/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/158:00 amHNL - ORD
1 stop18h 05mMultiple Airlines
Wed 12/317:44 pmORD - HNL
1 stop19h 28mMultiple Airlines
Deal found 11/15$455
This Kiwi.com deal was found by Cheapflights users on 11/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/54:04 pmOGG - ORD
1 stop34h 01mMultiple Airlines
Tue 12/99:06 pmORD - OGG
2 stops21h 23mMultiple Airlines
Deal found 11/16$456

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 17, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$364
(Delta)

One-way from

$182
(Kiwi.com)

Popular in

July

Cheapest in

September

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. 10% potential increase in price ($85 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($13 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 17, 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

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

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Tue 3/3

6:00 am-11:59 pm

2 stops13h 59m

Chicago O'Hare Intl

Wed 3/4

7:00 am-10:57 pm

1 stop19h 57m

$409

LihueChicago

LIH - ORD

LIHORD

Lihue

Tue 3/10

6:00 am-11:59 pm

2 stops12h 59m

Chicago O'Hare Intl

Wed 3/11

3:07 pm-11:47 am

1 stop25h 40m

$409

LihueChicago

LIH - ORD

LIHORD

Lihue

Tue 2/17

6:00 am-11:59 pm

2 stops13h 59m

Chicago O'Hare Intl

Thu 2/19

8:20 am-10:22 pm

2 stops18h 02m

$412

LihueChicago

LIH - ORD

LIHORD

Lihue

Tue 2/17

10:30 pm-2:05 pm

1 stop11h 35m

Chicago O'Hare Intl

Thu 2/19

9:28 am-5:11 pm

1 stop11h 43m

$423

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Tue 3/10

6:01 am-11:59 pm

2 stops12h 58m

Chicago O'Hare Intl

Wed 3/11

3:07 pm-10:46 pm

1 stop12h 39m

$442

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Wed 12/24

9:55 pm-1:20 pm

1 stop11h 25m

Chicago O'Hare Intl

Thu 1/1

7:25 am-3:48 pm

1 stop12h 23m

$443

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Fri 12/5

4:04 pm-6:05 am

1 stop34h 01m

Chicago O'Hare Intl

Tue 12/9

9:06 pm-2:29 pm

2 stops21h 23m

$456

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Tue 12/23

4:45 pm-9:01 am

1 stop12h 16m

Chicago O'Hare Intl

Mon 1/12

5:30 am-3:10 pm

1 stop13h 40m

$456

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Tue 4/7

8:47 am-5:07 am

2 stops15h 20m

Chicago O'Hare Intl

Sun 4/12

7:00 am-4:33 pm

2 stops14h 33m

$462

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/17

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 $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 17, 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 17, 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, American Airlines, and Delta can get you from Hawaii to Chicago in just under 11h 35m. Your travel time can differ by up to 2h 24m. Airlines will cover a distance of 4280 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 ($190), Delta ($212), and American Airlines ($242).

  • 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 Kona Intl - 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 $1,699, 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 $446 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 $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?

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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Dallas/Fort Worth to Midway flights
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Dulles Intl to Midway flights
Minneapolis to O'Hare Intl flights
Raleigh to O'Hare Intl flights
Charlotte to O'Hare Intl flights
Seattle to Midway flights
Hobby to Midway flights
George Bush Intcntl to O'Hare Intl flights
San Francisco to Midway flights
Minneapolis to Midway flights
Tampa to O'Hare Intl flights
Miami to O'Hare Intl flights
Baltimore to Midway flights
San Diego to O'Hare Intl flights
Austin to O'Hare Intl flights
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Portland to O'Hare Intl flights
Fort Lauderdale to O'Hare Intl flights
Newark to St. Louis flights
Denver to Midway flights
Orlando to O'Hare Intl flights
Cleveland to O'Hare Intl flights
Hartford to O'Hare Intl flights
LaGuardia to St. Louis flights
Dallas/Fort Worth to St. Louis flights
John F Kennedy Intl to St. Louis flights
Reagan-National to Midway flights
Denver to St. Louis flights

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 17, 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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