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$164+ 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 2/4. Fares are subject to change and may not be available on all flights or dates of travel.
HNL — CHI
Feb 7 — Feb 141
Sat 2/7
Sat 2/14
1 adult, Economy
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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 January 8, 2026.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$336
(Delta)

One-way from

$164
(Kiwi.com)

Popular in

July

Cheapest in

February

Average price

$721

Good round-trip deal

$447 or less

Good one-way deal

$239 or less
Provider with most accurate pricing for Honolulu-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Honolulu-Chicago (CHI) flights.
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From Hawaii to Chicago (CHI)
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One-way flight from Hawaii to Chicago (CHI)
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Highest demand for flights based on searches. 13% potential increase in price ($111 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($13 potential savings vs. average RT price).
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Average for round-trip flights in January 2026
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Price to beat on a round-trip flight from Hawaii to Chicago (CHI).
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Price to beat on a one-way flight from Hawaii to Chicago (CHI).
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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 January 8, 2026.

This Delta deal was found by Cheapflights users on 1/6. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/298:45 pmKOA - ORD
1 stop12h 37mDelta
Tue 2/37:20 amORD - KOA
2 stops16h 37mDelta
Deal found 1/6$336
This United Airlines deal was found by Cheapflights users on 1/7. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/296:05 pmHNL - ORD
Nonstop8h 11mUnited Airlines
Tue 2/39:30 amORD - HNL
Nonstop9h 27mUnited Airlines
Deal found 1/7$341
This Alaska Airlines deal was found by Cheapflights users on 1/7. 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 4/2910:41 pmOGG - ORD
1 stop11h 00mAlaska Airlines
Mon 5/47:59 pmORD - OGG
1 stop29h 53mAlaska Airlines
Deal found 1/7$342
This American Airlines deal was found by Cheapflights users on 1/7. 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 2/610:10 pmLIH - ORD
1 stop12h 06mAmerican Airlines
Mon 2/96:00 amORD - LIH
1 stop14h 37mAmerican Airlines
Deal found 1/7$347
This United Airlines deal was found by Cheapflights users on 1/8. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/136:05 pmHNL - ORD
Nonstop8h 09mUnited Airlines
Wed 2/1812:55 pmORD - HNL
1 stop12h 26mUnited Airlines
Deal found 1/8$351
This Alaska Airlines deal was found by Cheapflights users on 1/7. 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 2/251:10 pmKOA - ORD
1 stop21h 48mAlaska Airlines
Sat 3/73:54 pmORD - KOA
1 stop34h 03mAlaska Airlines
Deal found 1/7$354
This American Airlines deal was found by Cheapflights users on 1/6. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/299:20 pmKOA - ORD
1 stop11h 15mAmerican Airlines
Tue 2/37:00 amORD - KOA
1 stop11h 54mAmerican Airlines
Deal found 1/6$358
This Southwest deal was found by Cheapflights users on 1/6. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/181:50 pmHNL - MDW
1 stop11h 05mSouthwest
Tue 4/710:05 amMDW - HNL
1 stop15h 55mSouthwest
Deal found 1/6$360
This Delta deal was found by Cheapflights users on 1/7. 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 2/259:55 pmKOA - ORD
2 stops15h 47mDelta
Sat 3/77:15 amORD - KOA
2 stops16h 24mDelta
Deal found 1/7$361
This Expedia deal was found by Cheapflights users on 1/5. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/302:24 pmKOA - ORD
1 stop20h 05mMultiple Airlines
Tue 2/39:00 amORD - KOA
2 stops16h 30mMultiple Airlines
Deal found 1/5$364
This Delta deal was found by Cheapflights users on 1/7. 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 4/298:05 pmOGG - ORD
1 stop11h 20mDelta
Mon 5/47:20 amORD - OGG
2 stops17h 11mDelta
Deal found 1/7$364
This Alaska Airlines deal was found by Cheapflights users on 1/8. 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 2/278:11 amHNL - ORD
1 stop11h 48mMultiple Airlines
Mon 3/25:29 pmORD - HNL
2 stops21h 21mMultiple Airlines
Deal found 1/8$365

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 January 8, 2026.
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 1/29

8:45 pm-1:22 pm

1 stop12h 37m

Chicago O'Hare Intl

Tue 2/3

7:20 am-7:57 pm

2 stops16h 37m

$336

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Wed 2/25

9:55 pm-1:22 pm

1 stop11h 27m

Chicago O'Hare Intl

Sat 3/7

7:15 am-7:39 pm

2 stops16h 24m

$336

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Wed 4/29

10:41 pm-2:41 pm

1 stop11h 00m

Chicago O'Hare Intl

Mon 5/4

7:59 pm-8:52 pm

1 stop29h 53m

$342

LihueChicago

LIH - ORD

LIHORD

Lihue

Fri 2/6

10:10 pm-3:30 pm

1 stop13h 20m

Chicago O'Hare Intl

Mon 2/9

9:10 am-4:37 pm

1 stop11h 27m

$347

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Fri 2/27

8:30 pm-12:37 pm

1 stop12h 07m

Chicago O'Hare Intl

Mon 3/2

9:30 am-2:54 pm

Nonstop9h 24m

$351

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Thu 2/26

12:35 pm-5:03 am

1 stop12h 28m

Chicago O'Hare Intl

Mon 3/2

9:30 am-2:54 pm

Nonstop9h 24m

$351

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Wed 2/25

1:10 pm-2:58 pm

1 stop21h 48m

Chicago O'Hare Intl

Sat 3/7

3:54 pm-9:57 pm

1 stop34h 03m

$354

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Fri 1/30

9:44 pm-12:32 pm

1 stop10h 48m

Chicago O'Hare Intl

Tue 2/3

6:54 am-3:48 pm

1 stop12h 54m

$358

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Thu 1/29

9:20 pm-12:35 pm

1 stop11h 15m

Chicago O'Hare Intl

Tue 2/3

7:00 am-2:54 pm

1 stop11h 54m

$358

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Wed 2/18

10:11 pm-12:31 pm

1 stop10h 20m

Chicago O'Hare Intl

Sun 2/22

9:25 am-6:59 pm

1 stop13h 34m

$358

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/7

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 January 8, 2026.

When flying from Hawaii to Chicago, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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 January 8, 2026.

The most flights from USHI to CHI are scheduled on a Tuesday (7 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?

    Delta, Alaska Airlines, and American Airlines can get you from Hawaii to Chicago in just under 11h. Your travel time can differ by up to 2h 20m. 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 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 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 (83%), United Airlines (83%), Air New Zealand (83%).

  • What are the cheapest flights from Hawaii to Chicago?

    While on average a flight from Hawaii to Chicago is generally $1,145, our data shows the cheapest flight currently is $254. When looking at the most popular route, (Honolulu - Chicago O'Hare Intl), you can expect to pay $341 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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Philadelphia to Midway flights
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Love Field to Midway flights
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Denver 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 January 8, 2026.
AirlineCheapestAverageFlexibilityOn-time
Hawaiian AirlinesCheapest$322Average$743FlexibilityNo cancel feeOn-time85%
DeltaCheapest$383Average$587FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$447Average$834FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$455Average$719FlexibilityNo cancel feeOn-time71%
Alaska AirlinesCheapest$468Average$815FlexibilityNo cancel feeOn-time75%
SouthwestCheapest$581Average$773FlexibilityNo cancel feeOn-time63%

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