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$186+ 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 2/9. Fares are subject to change and may not be available on all flights or dates of travel.
HNL — CHI
Jan 22 — Jan 291
Thu 1/22
Thu 1/29
1 adult, Economy
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Cheap 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 23, 2025.

This Alaska Airlines deal was found by Cheapflights users on 12/20. 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 12/244:04 pmHNL - ORD
1 stop16h 09mMultiple Airlines
Sun 1/119:00 amORD - HNL
1 stop31h 48mMultiple Airlines
Deal found 12/20$531
This Delta deal was found by Cheapflights users on 12/22. 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 12/22$570
This Alaska Airlines deal was found by Cheapflights users on 12/21. 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 12/242:15 pmHNL - ORD
1 stop12h 14mMultiple Airlines
Wed 1/76:06 pmORD - HNL
1 stop21h 12mMultiple Airlines
Deal found 12/21$597
This Alaska Airlines deal was found by Cheapflights users on 12/20. 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 12/2711:28 pmHNL - ORD
1 stop11h 09mMultiple Airlines
Tue 1/276:06 pmORD - HNL
1 stop21h 05mMultiple Airlines
Deal found 12/20$633
This Delta deal was found by Cheapflights users on 12/20. 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 12/246:30 pmHNL - ORD
1 stop13h 42mDelta
Sun 1/117:20 amORD - HNL
2 stops18h 08mDelta
Deal found 12/20$635
This American Airlines deal was found by Cheapflights users on 12/21. 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 12/247:00 pmHNL - ORD
Nonstop7h 57mAmerican Airlines
Sun 1/115:05 amORD - HNL
1 stop12h 58mAmerican Airlines
Deal found 12/21$663
This American Airlines deal was found by Cheapflights users on 12/20. 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.
Tue 12/237:00 pmHNL - ORD
Nonstop7h 57mAmerican Airlines
Mon 1/125:05 amORD - HNL
1 stop12h 58mAmerican Airlines
Deal found 12/20$666
This Alaska Airlines deal was found by Cheapflights users on 12/20. 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 12/208:13 amHNL - ORD
1 stop11h 46mMultiple Airlines
Sat 1/103:44 pmORD - HNL
1 stop33h 37mMultiple Airlines
Deal found 12/20$668
This American Airlines deal was found by Cheapflights users on 12/21. 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.
Tue 12/236:30 pmKOA - ORD
1 stop10h 10mAmerican Airlines
Mon 1/510:40 amORD - KOA
1 stop12h 11mAmerican Airlines
Deal found 12/21$683
This Delta deal was found by Cheapflights users on 12/21. 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 12/238:55 pmKOA - ORD
2 stops15h 26mDelta
Mon 1/57:30 amORD - KOA
1 stop15h 17mDelta
Deal found 12/21$689
This Southwest deal was found by Cheapflights users on 12/21. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/239:15 pmKOA - MDW
1 stop12h 25mSouthwest
Mon 1/57:45 amMDW - KOA
2 stops17h 35mSouthwest
Deal found 12/21$743
This Southwest deal was found by Cheapflights users on 12/21. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/239:15 pmKOA - ORD
2 stops12h 15mSouthwest
Mon 1/57:15 amORD - KOA
2 stops18h 05mSouthwest
Deal found 12/21$749

Find 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 23, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$362
(American Airlines)

One-way from

$186
(Kiwi.com)

Popular in

July

Cheapest in

September

Average price

$741

Good round-trip deal

$485 or less

Good one-way deal

$242 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. 11% potential increase in price ($95 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 23, 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

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Thu 1/22

7:00 pm-7:00 am

Nonstop8h 00m

Chicago O'Hare Intl

Tue 1/27

10:00 am-3:21 pm

Nonstop9h 21m

$362

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Thu 1/15

5:00 pm-9:43 am

1 stop12h 43m

Chicago O'Hare Intl

Thu 1/22

7:00 am-4:43 pm

1 stop13h 43m

$375

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Thu 1/22

11:16 pm-2:29 pm

1 stop11h 13m

Chicago O'Hare Intl

Tue 1/27

3:44 pm-12:48 pm

1 stop25h 04m

$381

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Tue 1/27

11:59 pm-11:37 pm

1 stop19h 38m

Chicago O'Hare Intl

Tue 2/3

3:44 pm-2:27 pm

2 stops26h 43m

$389

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Wed 1/28

6:00 am-11:37 pm

2 stops13h 37m

Chicago O'Hare Intl

Tue 2/3

9:00 am-10:59 pm

1 stop17h 59m

$390

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Wed 1/21

11:59 pm-11:37 pm

1 stop19h 38m

Chicago O'Hare Intl

Wed 1/28

9:00 am-10:59 pm

1 stop17h 59m

$392

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Thu 1/29

11:59 pm-11:37 pm

1 stop19h 38m

Chicago O'Hare Intl

Tue 2/3

9:00 am-10:59 pm

1 stop17h 59m

$394

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Thu 1/29

11:59 pm-2:29 pm

1 stop10h 30m

Chicago O'Hare Intl

Wed 2/4

9:00 am-10:59 pm

1 stop17h 59m

$394

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Wed 1/28

6:00 am-11:37 pm

2 stops13h 37m

Chicago O'Hare Intl

Mon 2/2

9:00 am-10:59 pm

1 stop17h 59m

$399

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Wed 1/28

6:00 am-11:37 pm

2 stops13h 37m

Chicago O'Hare Intl

Thu 2/5

9:00 am-10:59 pm

1 stop17h 59m

$399

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/22

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 $689). 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 23, 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 23, 2025.

The most flights from USHI to CHI are scheduled on a Tuesday (8 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (6 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?

    American Airlines, United Airlines, and Alaska Airlines can get you from Hawaii to Chicago in just under 8h. Your travel time can differ by up to 11h 38m. Airlines will cover a distance of 4234 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 Southwest ($210), American Airlines ($211), and Delta ($211).

  • 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: United Airlines (85%), Air New Zealand (85%), Avianca (78%).

  • What are the cheapest flights from Hawaii to Chicago?

    While on average a flight from Hawaii to Chicago is generally $843, 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 $359 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 $689). 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
Merrillville
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.
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Minneapolis to Midway flights
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Boston to Midway flights
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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 23, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$305Average$620FlexibilityNo cancel feeOn-timeN/A
Hawaiian AirlinesCheapest$322Average$743FlexibilityNo cancel feeOn-time85%
United AirlinesCheapest$447Average$925FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$455Average$718FlexibilityNo cancel feeOn-time71%
Alaska AirlinesCheapest$468Average$800FlexibilityNo cancel feeOn-time75%
SouthwestCheapest$581Average$775FlexibilityNo cancel feeOn-time63%

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