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$190+ 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 11/24. Fares are subject to change and may not be available on all flights or dates of travel.
HNL — CHI
Oct 17 — Oct 241
Fri 10/17
Fri 10/24
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 September 17, 2025.

Round-trip from

$423
(Alaska Airlines)

One-way from

$190
(Alaska Airlines)

Popular in

July

Cheapest in

November

Average price

$618

Good round-trip deal

$280 or less

Good one-way deal

$327 or less
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 ($110 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($14 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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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 September 17, 2025.

This Alaska Airlines deal was found by Cheapflights users on 9/17. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/511:59 pmOGG - ORD
1 stop20h 00mAlaska Airlines
Sun 11/98:59 pmORD - OGG
1 stop29h 51mAlaska Airlines
Deal found 9/17$423
This Delta deal was found by Cheapflights users on 9/16. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/179:29 pmLIH - ORD
1 stop15h 49mDelta
Mon 11/247:47 amORD - LIH
1 stop16h 17mDelta
Deal found 9/16$466
This Delta deal was found by Cheapflights users on 9/16. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/231:20 pmHNL - ORD
2 stops14h 10mDelta
Mon 10/277:37 amORD - HNL
1 stop16h 32mDelta
Deal found 9/16$471
This Delta deal was found by Cheapflights users on 9/16. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/234:45 pmHNL - ORD
1 stop12h 16mDelta
Wed 1/77:30 amORD - HNL
1 stop17h 03mDelta
Deal found 9/16$472
This Delta deal was found by Cheapflights users on 9/16. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/29:40 pmLIH - ORD
1 stop10h 40mDelta
Tue 10/147:37 amORD - LIH
1 stop16h 28mDelta
Deal found 9/16$473
This Delta deal was found by Cheapflights users on 9/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/174:45 pmHNL - MDW
1 stop12h 07mDelta
Mon 1/126:00 amMDW - HNL
1 stop13h 12mDelta
Deal found 9/15$475
This Delta deal was found by Cheapflights users on 9/17. 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.
Tue 12/234:45 pmHNL - ORD
1 stop12h 16mDelta
Mon 1/127:00 amORD - HNL
1 stop12h 29mDelta
Deal found 9/17$475
This United Airlines deal was found by Cheapflights users on 9/15. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/158:00 pmKOA - ORD
1 stop12h 12mUnited Airlines
Fri 10/176:15 amORD - KOA
1 stop10h 41mUnited Airlines
Deal found 9/15$477
This American Airlines deal was found by Cheapflights users on 9/15. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/267:00 pmOGG - ORD
1 stop11h 36mAmerican Airlines
Sun 11/305:18 amORD - OGG
1 stop11h 59mAmerican Airlines
Deal found 9/15$479
This Delta deal was found by Cheapflights users on 9/17. 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.
Thu 10/232:50 pmHNL - ORD
1 stop12h 00mDelta
Sun 10/267:37 amORD - HNL
1 stop16h 32mDelta
Deal found 9/17$479
This American Airlines deal was found by Cheapflights users on 9/16. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/209:45 pmLIH - ORD
1 stop18h 21mAmerican Airlines
Sun 1/47:00 amORD - LIH
1 stop11h 25mAmerican Airlines
Deal found 9/16$481
This Alaska Airlines deal was found by Cheapflights users on 9/17. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/171:05 pmHNL - ORD
1 stop12h 19mAlaska Airlines
Sat 10/253:50 pmORD - HNL
1 stop25h 32mAlaska Airlines
Deal found 9/17$481

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 September 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

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Wed 11/5

11:59 pm-11:59 pm

1 stop20h 00m

Chicago O'Hare Intl

Sun 11/9

8:59 pm-10:50 pm

1 stop29h 51m

$423

LihueChicago

LIH - ORD

LIHORD

Lihue

Mon 11/17

9:29 pm-5:18 pm

1 stop15h 49m

Chicago O'Hare Intl

Mon 11/24

7:47 am-8:04 pm

1 stop16h 17m

$466

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Sun 3/1

8:15 am-11:44 pm

1 stop11h 29m

Chicago O'Hare Intl

Tue 3/3

5:50 am-3:19 pm

1 stop13h 29m

$471

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Tue 12/23

4:45 pm-9:01 am

1 stop12h 16m

Chicago O'Hare Intl

Wed 1/7

7:30 am-8:33 pm

1 stop17h 03m

$472

LihueChicago

LIH - ORD

LIHORD

Lihue

Thu 10/2

9:40 pm-1:20 pm

1 stop10h 40m

Chicago O'Hare Intl

Tue 10/14

7:37 am-7:05 pm

1 stop16h 28m

$473

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Tue 12/23

4:45 pm-9:01 am

1 stop12h 16m

Chicago O'Hare Intl

Mon 1/12

7:00 am-3:29 pm

1 stop12h 29m

$475

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Wed 10/15

8:00 pm-1:12 pm

1 stop12h 12m

Chicago O'Hare Intl

Fri 10/17

6:15 am-11:56 am

1 stop10h 41m

$477

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Tue 10/14

10:31 pm-5:10 pm

1 stop13h 39m

Chicago O'Hare Intl

Tue 10/21

6:45 am-7:09 pm

2 stops17h 24m

$478

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Mon 10/27

10:31 pm-5:10 pm

1 stop13h 39m

Chicago O'Hare Intl

Mon 11/3

7:10 am-2:51 pm

1 stop11h 41m

$479

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Mon 11/17

4:45 pm-1:07 pm

2 stops16h 22m

Chicago Midway

Mon 1/12

6:00 am-3:12 pm

1 stop13h 12m

$480

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/15

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, August is the cheapest month in which you can book a flight from Hawaii to Chicago (average of $245). Flying from Hawaii to Chicago in March is currently the most expensive (average of $321). 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 September 17, 2025.

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 September 17, 2025.

The most flights from USHI to CHI are scheduled on a Monday (4 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (3 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 United Airlines can get you from Hawaii to Chicago in just under 12h 12m. Your travel time can differ by up to 7h 48m. Airlines will cover a distance of 4205 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), Hawaiian Airlines ($190), and Delta ($205).

  • 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 (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 $1,700, 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 $467 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, August is the cheapest month in which you can book a flight from Hawaii to Chicago (average of $245). Flying from Hawaii to Chicago in March is currently the most expensive (average of $321). 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
Benton Harbor
Porter
Chesterton

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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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John F Kennedy Intl to Midway flights
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Atlanta to Midway flights
LaGuardia to Midway flights
Los Angeles to Midway flights
Dulles Intl to Midway flights
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Minneapolis to O'Hare Intl flights
Philadelphia to Midway flights
Sky Harbor Intl to O'Hare Intl flights
Austin to O'Hare Intl flights
Charlotte to O'Hare Intl flights
Denver to Midway flights
San Francisco to Midway flights
George Bush Intcntl to O'Hare Intl flights
Burbank to O'Hare Intl flights
Raleigh to O'Hare Intl flights
San Jose to O'Hare Intl flights
Providence to O'Hare Intl flights
Miami to O'Hare Intl flights
Hobby to Midway flights
Portland to O'Hare Intl flights
Orlando to O'Hare Intl flights
Seattle to Midway flights
Cleveland to O'Hare Intl flights
Fort Lauderdale to O'Hare Intl flights
Boston to Midway flights
Minneapolis to Midway flights
Love Field to O'Hare Intl flights
Reagan-National to Midway flights
Hartford to O'Hare Intl flights
Tampa to O'Hare Intl 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 September 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$231Average$626FlexibilityNo cancel feeOn-timeN/A
Hawaiian AirlinesCheapest$322Average$743FlexibilityNo cancel feeOn-time85%
American AirlinesCheapest$399Average$730FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$429Average$836FlexibilityNo cancel feeOn-time69%
Alaska AirlinesCheapest$458Average$764FlexibilityNo cancel feeOn-time75%
SouthwestCheapest$617Average$788FlexibilityNo cancel feeOn-time63%

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