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$191+ 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 1/13. Fares are subject to change and may not be available on all flights or dates of travel.
HNL — CHI
Nov 26 — Dec 31
Wed 11/26
Wed 12/3
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 October 27, 2025.

This Alaska Airlines deal was found by Cheapflights users on 10/27. 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 11/173:20 pmOGG - ORD
1 stop11h 02mAlaska Airlines
Tue 11/189:20 amORD - OGG
2 stops16h 45mAlaska Airlines
Deal found 10/27$422
This KAYAK deal was found by Cheapflights users on 10/27. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/173:20 pmOGG - ORD
1 stop11h 02mHawaiian Airlines
Tue 11/182:54 pmORD - OGG
1 stop11h 56mHawaiian Airlines
Deal found 10/27$426
This Kiwi.com deal was found by Cheapflights users on 10/25. 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.
Sun 12/78:00 amHNL - ORD
1 stop12h 13mMultiple Airlines
Mon 12/86:50 amORD - HNL
1 stop12h 47mMultiple Airlines
Deal found 10/25$427
This American Airlines deal was found by Cheapflights users on 10/26. 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.
Mon 11/1010:39 pmLIH - ORD
1 stop11h 34mAmerican Airlines
Fri 11/147:00 amORD - LIH
1 stop12h 59mAmerican Airlines
Deal found 10/26$453
This Kiwi.com deal was found by Cheapflights users on 10/25. 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 11/132:25 pmHNL - ORD
2 stops28h 35mMultiple Airlines
Mon 11/176:30 amORD - HNL
1 stop18h 10mMultiple Airlines
Deal found 10/25$453
This Delta deal was found by Cheapflights users on 10/26. 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 11/109:40 pmLIH - ORD
1 stop15h 38mDelta
Fri 11/146:45 amORD - LIH
2 stops17h 19mDelta
Deal found 10/26$458
This Delta deal was found by Cheapflights users on 10/26. 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 11/1010:55 pmLIH - MDW
2 stops15h 23mDelta
Fri 11/149:34 amMDW - LIH
2 stops14h 30mDelta
Deal found 10/26$464
This Kiwi.com deal was found by Cheapflights users on 10/25. 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 12/44:06 pmHNL - ORD
1 stop28h 07mMultiple Airlines
Mon 12/86:50 amORD - HNL
1 stop18h 19mMultiple Airlines
Deal found 10/25$471
This Alaska Airlines deal was found by Cheapflights users on 10/26. 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 12/112:20 pmKOA - ORD
1 stop29h 30mAlaska Airlines
Mon 12/158:55 amORD - KOA
1 stop11h 05mAlaska Airlines
Deal found 10/26$486
This Alaska Airlines deal was found by Cheapflights users on 10/27. 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 12/2311:59 pmHNL - ORD
1 stop26h 30mAlaska Airlines
Mon 1/123:49 pmORD - HNL
1 stop24h 59mAlaska Airlines
Deal found 10/27$492
This Delta deal was found by Cheapflights users on 10/26. 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 11/119:40 pmLIH - ORD
1 stop11h 54mDelta
Sat 11/157:47 amORD - LIH
1 stop16h 17mDelta
Deal found 10/26$498
This Kiwi.com deal was found by Cheapflights users on 10/25. 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
Sun 12/712:59 pmORD - HNL
1 stop21h 33mMultiple Airlines
Deal found 10/25$500

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 October 27, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$422
(Alaska Airlines)

One-way from

$195
(Alaska Airlines)

Popular in

July

Cheapest in

October

Average price

$553

Good round-trip deal

$350 or less

Good one-way deal

$305 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. 13% potential increase in price ($108 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 October 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 October 27, 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

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Mon 11/17

3:20 pm-6:22 am

1 stop11h 02m

Chicago O'Hare Intl

Tue 11/18

9:20 am-10:05 pm

2 stops16h 45m

$422

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Tue 3/3

8:46 am-5:04 am

2 stops16h 18m

Chicago O'Hare Intl

Wed 3/4

9:00 am-10:48 pm

1 stop17h 48m

$422

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Mon 11/17

3:20 pm-6:22 am

1 stop11h 02m

Chicago O'Hare Intl

Tue 11/18

2:54 pm-10:50 pm

1 stop11h 56m

$426

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Tue 3/3

6:00 am-11:10 pm

2 stops13h 10m

Chicago O'Hare Intl

Wed 3/4

2:59 pm-2:46 pm

1 stop27h 47m

$429

LihueChicago

LIH - ORD

LIHORD

Lihue

Mon 11/10

10:39 pm-2:13 pm

1 stop11h 34m

Chicago O'Hare Intl

Fri 11/14

7:00 am-3:59 pm

1 stop12h 59m

$453

LihueChicago

LIH - ORD

LIHORD

Lihue

Mon 11/10

9:40 pm-5:18 pm

1 stop15h 38m

Chicago O'Hare Intl

Fri 11/14

6:45 am-8:04 pm

2 stops17h 19m

$458

LihueChicago

LIH - ORD

LIHORD

Lihue

Tue 11/11

9:40 pm-1:34 pm

1 stop11h 54m

Chicago O'Hare Intl

Sat 11/15

7:20 am-8:04 pm

2 stops16h 44m

$458

LihueChicago

LIH - MDW

LIHMDW

Lihue

Mon 11/10

10:55 pm-6:18 pm

2 stops15h 23m

Chicago Midway

Fri 11/14

9:34 am-8:04 pm

2 stops14h 30m

$464

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Sun 3/1

7:00 am-11:59 pm

1 stop12h 59m

Chicago O'Hare Intl

Tue 3/3

10:00 am-7:40 pm

1 stop13h 40m

$471

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Sun 3/1

8:15 am-11:44 pm

1 stop11h 29m

Chicago O'Hare Intl

Tue 3/3

7:30 am-8:33 pm

1 stop17h 03m

$471

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/26

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 October 27, 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.

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 American Airlines can get you from Hawaii to Chicago in just under 11h 02m. Your travel time can differ by up to 32m. 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 ($195), American Airlines ($212), 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, Kahului - Chicago O'Hare Intl or Honolulu - Chicago Midway 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 $1,583, 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 $292 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?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Porter
Benton Harbor

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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.
John F Kennedy Intl to O'Hare Intl flights
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Dallas/Fort Worth to O'Hare Intl flights
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Baltimore to O'Hare Intl flights
Boston to O'Hare Intl flights
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Newark to Midway flights
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Philadelphia to O'Hare Intl flights
Dallas/Fort Worth to Midway flights
Denver to O'Hare Intl flights
Atlanta to O'Hare Intl flights
John F Kennedy Intl to Midway flights
Baltimore to Midway flights
Tampa to O'Hare Intl flights
Sky Harbor Intl to O'Hare Intl flights
Atlanta to Midway flights
Ontario to O'Hare Intl flights
Minneapolis to O'Hare Intl flights
Los Angeles to Midway flights
Fort Lauderdale to O'Hare Intl flights
LaGuardia to Midway flights
Dulles Intl to Midway flights
Austin to O'Hare Intl flights
Charlotte to O'Hare Intl flights
Hobby to Midway flights
Orlando to O'Hare Intl flights
George Bush Intcntl to O'Hare Intl flights
Hobby to O'Hare Intl flights
Reagan-National to Midway flights
Raleigh to O'Hare Intl flights
Minneapolis to Midway flights
Denver to Midway flights
Portland to O'Hare Intl flights
San Diego to O'Hare Intl flights
Santa Ana to O'Hare Intl flights
Love Field to O'Hare Intl flights
Cleveland to O'Hare Intl flights
Philadelphia to Midway flights
Newark to St. Louis flights
Boston to Midway flights
Hartford to O'Hare Intl flights
San Francisco to Midway flights
Miami to O'Hare Intl flights
Orlando to Midway flights
LaGuardia 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 October 27, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$218Average$640FlexibilityNo cancel feeOn-timeN/A
Hawaiian AirlinesCheapest$322Average$743FlexibilityNo cancel feeOn-time85%
American AirlinesCheapest$429Average$729FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$432Average$851FlexibilityNo cancel feeOn-time69%
Alaska AirlinesCheapest$467Average$811FlexibilityNo cancel feeOn-time75%
SouthwestCheapest$516Average$771FlexibilityNo cancel feeOn-time63%

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