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$232+ 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 5/2. Fares are subject to change and may not be available on all flights or dates of travel.
HNL — CHI
Apr 22 — Apr 291
Tue 4/22
Tue 4/29
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 April 17, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$467
(Alaska Airlines)

One-way from

$232
(American Airlines)

Popular in

July

Cheapest in

October

Average price

$699

Good round-trip deal

$718 or less

Good one-way deal

$395 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. 9% potential increase in price ($71 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($18 potential savings vs. average RT price).
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Average for round-trip flights in April 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 April 17, 2025.

This Alaska Airlines deal was found by Cheapflights users on 4/16. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2812:13 pmKOA - ORD
1 stop11h 51mAlaska Airlines
Sun 9/76:24 amORD - KOA
1 stop14h 00mAlaska Airlines
Deal found 4/16$467
This Delta deal was found by Cheapflights users on 4/16. 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 9/29:45 pmKOA - ORD
1 stop10h 39mDelta
Wed 9/107:30 amORD - KOA
1 stop15h 14mDelta
Deal found 4/16$495
This Delta deal was found by Cheapflights users on 4/17. 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 5/213:09 pmHNL - ORD
1 stop16h 39mDelta
Wed 6/46:20 pmORD - HNL
1 stop22h 35mDelta
Deal found 4/17$515
This Alaska Airlines deal was found by Cheapflights users on 4/16. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/218:00 amOGG - ORD
1 stop10h 59mAlaska Airlines
Tue 5/277:51 pmORD - OGG
1 stop31h 22mAlaska Airlines
Deal found 4/16$517
This Delta deal was found by Cheapflights users on 4/17. 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 5/81:20 pmHNL - MDW
2 stops14h 16mDelta
Sun 5/119:20 amMDW - HNL
2 stops16h 14mDelta
Deal found 4/17$524
This Alaska Airlines deal was found by Cheapflights users on 4/17. 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.
Mon 8/189:45 pmHNL - ORD
1 stop15h 33mAlaska Airlines
Tue 8/262:05 pmORD - HNL
1 stop11h 20mAlaska Airlines
Deal found 4/17$527
This Delta deal was found by Cheapflights users on 4/16. 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 5/208:38 pmKOA - MDW
2 stops16h 07mDelta
Tue 6/39:20 amMDW - KOA
2 stops14h 50mDelta
Deal found 4/16$542
This Southwest deal was found by Cheapflights users on 4/17. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/179:05 pmHNL - ORD
2 stops13h 15mSouthwest
Sat 9/206:15 amORD - HNL
2 stops14h 50mSouthwest
Deal found 4/17$590
This Delta deal was found by Cheapflights users on 4/17. 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 5/218:50 pmOGG - ORD
2 stops12h 38mDelta
Tue 5/276:24 amORD - OGG
2 stops18h 01mDelta
Deal found 4/17$603
This Southwest deal was found by Cheapflights users on 4/17. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/48:05 amHNL - MDW
1 stop11h 25mSouthwest
Sun 9/1410:25 pmMDW - HNL
1 stop16h 55mSouthwest
Deal found 4/17$603
This Delta deal was found by Cheapflights users on 4/17. 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 5/2112:00 pmOGG - MDW
2 stops15h 36mDelta
Tue 5/279:20 amMDW - OGG
2 stops15h 05mDelta
Deal found 4/17$661
This Southwest deal was found by Cheapflights users on 4/17. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/88:30 pmKOA - MDW
1 stop13h 05mSouthwest
Wed 5/149:25 pmMDW - KOA
2 stops19h 45mSouthwest
Deal found 4/17$665

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 April 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

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Thu 8/28

12:13 pm-5:04 am

1 stop11h 51m

Chicago O'Hare Intl

Sun 9/7

6:24 am-3:24 pm

1 stop14h 00m

$467

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Tue 9/2

9:45 pm-1:24 pm

1 stop10h 39m

Chicago O'Hare Intl

Mon 9/8

7:30 am-5:44 pm

1 stop15h 14m

$495

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Wed 5/21

3:09 pm-12:48 pm

1 stop16h 39m

Chicago O'Hare Intl

Wed 6/4

6:20 pm-11:55 am

1 stop22h 35m

$515

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Wed 5/21

8:00 am-11:59 pm

1 stop10h 59m

Chicago O'Hare Intl

Tue 5/27

7:51 pm-10:13 pm

1 stop31h 22m

$517

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Thu 5/8

1:20 pm-8:36 am

2 stops14h 16m

Chicago Midway

Sun 5/11

9:20 am-8:34 pm

2 stops16h 14m

$524

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Mon 8/18

9:45 pm-6:18 pm

1 stop15h 33m

Chicago O'Hare Intl

Wed 8/27

2:05 pm-8:25 pm

1 stop11h 20m

$527

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Tue 5/20

8:38 pm-5:45 pm

2 stops16h 07m

Chicago Midway

Tue 6/3

9:20 am-7:10 pm

2 stops14h 50m

$542

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Wed 9/17

9:05 pm-3:20 pm

2 stops13h 15m

Chicago O'Hare Intl

Sat 9/20

6:15 am-4:05 pm

2 stops14h 50m

$590

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Thu 9/4

8:05 am-12:30 am

1 stop11h 25m

Chicago Midway

Sun 9/14

10:25 pm-10:20 am

1 stop16h 55m

$603

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Wed 5/21

8:50 pm-2:28 pm

2 stops12h 38m

Chicago O'Hare Intl

Tue 5/27

6:24 am-7:25 pm

2 stops18h 01m

$603

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/17

Showing 1-10 of 58 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 April 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 April 17, 2025.

The most flights from USHI to CHI are scheduled on a Monday (3 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (3 on average).

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated April 17, 2025.
Read through reviews of airlines operating flights from Hawaii to Chicago, such as Alaska Airlines, Southwest and Delta. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
9,882 reviews

Food

7.1

Overall

8.0

Boarding

8.2

Entertainment

7.1

Comfort

7.9

Crew

8.5

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Alaska Airlines
8.0
Very good
9,882 reviews
Alaska Airlines
8.0
Very good
9,882 reviews

Food

7.1

Overall

8.0

Boarding

8.2

Entertainment

7.1

Comfort

7.9

Crew

8.5

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Southwest
8.0
Very good
4,280 reviews
Alaska Airlines
8.0
Very good
9,882 reviews

Food

7.1

Overall

8.0

Boarding

8.2

Entertainment

7.1

Comfort

7.9

Crew

8.5

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Delta
8.0
Very good
7,917 reviews
Alaska Airlines
8.0
Very good
9,882 reviews

Food

7.1

Overall

8.0

Boarding

8.2

Entertainment

7.1

Comfort

7.9

Crew

8.5

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Hawaiian Airlines
7.9
Good
2,382 reviews
Alaska Airlines
8.0
Very good
9,882 reviews

Food

7.1

Overall

8.0

Boarding

8.2

Entertainment

7.1

Comfort

7.9

Crew

8.5

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
United Airlines
7.4
Good
8,667 reviews
Alaska Airlines
8.0
Very good
9,882 reviews

Food

7.1

Overall

8.0

Boarding

8.2

Entertainment

7.1

Comfort

7.9

Crew

8.5

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >

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.

  • 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 American Airlines ($232), Delta ($257), and Hawaiian Airlines ($260).

  • 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: Air New Zealand (88%), Avianca (88%), United Airlines (82%).

  • What are the cheapest flights from Hawaii to Chicago?

    While on average a flight from Hawaii to Chicago is generally $2,204, our data shows the cheapest flight currently is $263. 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 Hawaii?

Book flights to Hawaii if you plan to visit one of these locations
Merrillville
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
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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Boston to Midway flights
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Top 5 airlines flying from Hawaii to Chicago

Discover the top 5 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 April 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
Alaska AirlinesCheapest$220Average$670FlexibilityNo cancel feeOn-time75%
DeltaCheapest$222Average$652FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$349Average$570FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$392Average$827FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$418Average$740FlexibilityNo cancel feeOn-time63%

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