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$289+ Cheap flights from The Big Island 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 3/9. Fares are subject to change and may not be available on all flights or dates of travel.
KOA — CHI
Feb 3 — Feb 101
Mon 2/3
Mon 2/10
1 adult, Economy
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Cheap flight deals from The Big Island to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from The Big Island (zzFUI) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated January 29, 2025.

Round-trip from

$461
(Delta)

One-way from

$289
(Alaska Airlines)

Good one-way deal

$324 or less
From The Big Island to Chicago (CHI)
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One-way flight from The Big Island to Chicago (CHI)
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Price to beat on a one-way flight from The Big Island to Chicago (CHI).
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Find flight deals from The Big Island to Chicago

Cheapest flights from The Big Island to Chicago
Explore the most affordable flight options available from The Big Island to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 29, 2025.

This Delta deal was found by Cheapflights users on 1/28. 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 4/228:30 pmKOA - ORD
1 stop12h 01mDelta
Wed 4/306:40 amORD - KOA
2 stops16h 59mDelta
Deal found 1/28$461
This Delta deal was found by Cheapflights users on 1/28. 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 4/229:30 pmKOA - MDW
2 stops14h 33mDelta
Wed 4/309:30 amMDW - KOA
2 stops14h 09mDelta
Deal found 1/28$506
This American Airlines deal was found by Cheapflights users on 1/28. 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 5/19:16 pmKOA - ORD
1 stop11h 59mAmerican Airlines
Mon 5/56:00 amORD - KOA
1 stop13h 39mAmerican Airlines
Deal found 1/28$522
This Hawaiian Airlines deal was found by Cheapflights users on 1/27. 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 Hawaiian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/201:04 pmKOA - ORD
1 stop11h 36mHawaiian Airlines
Tue 6/36:00 amORD - KOA
1 stop12h 34mHawaiian Airlines
Deal found 1/27$576
This Southwest deal was found by Cheapflights users on 1/28. 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 5/18:30 pmKOA - MDW
1 stop10h 15mSouthwest
Mon 5/58:00 amMDW - KOA
2 stops15h 10mSouthwest
Deal found 1/28$591
This Alaska Airlines deal was found by Cheapflights users on 1/28. 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 9/198:00 amKOA - ORD
1 stop24h 04mAlaska Airlines
Sat 9/275:50 pmORD - KOA
2 stops22h 05mAlaska Airlines
Deal found 1/28$629
This United Airlines deal was found by Cheapflights users on 1/28. 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 5/11:10 pmKOA - ORD
1 stop17h 57mUnited Airlines
Mon 5/57:45 pmORD - KOA
1 stop21h 10mUnited Airlines
Deal found 1/28$641
This Southwest deal was found by Cheapflights users on 1/28. 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 5/16:00 amITO - ORD
2 stops12h 40mSouthwest
Mon 5/56:15 amORD - ITO
2 stops16h 55mSouthwest
Deal found 1/28$664
This United Airlines deal was found by Cheapflights users on 1/28. 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 5/18:22 amITO - ORD
2 stops23h 53mUnited Airlines
Mon 5/59:05 pmORD - ITO
2 stops27h 05mUnited Airlines
Deal found 1/28$813
This Alaska Airlines deal was found by Cheapflights users on 1/28. 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 2/1211:29 amITO - ORD
2 stops25h 29mAlaska Airlines
Sun 2/167:00 pmORD - ITO
2 stops24h 15mAlaska Airlines
Deal found 1/28$900

Find flights from The Big Island to Chicago within your budget

Customize your flight search to find flights from The Big Island 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 29, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Tue 4/22

8:30 pm-1:31 pm

1 stop12h 01m

Chicago O'Hare Intl

Wed 4/30

6:40 am-6:39 pm

2 stops16h 59m

$461

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Tue 4/22

9:30 pm-5:03 pm

2 stops14h 33m

Chicago Midway

Wed 4/30

9:30 am-6:39 pm

2 stops14h 09m

$506

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Thu 5/1

9:16 pm-2:15 pm

1 stop11h 59m

Chicago O'Hare Intl

Mon 5/5

6:00 am-2:39 pm

1 stop13h 39m

$522

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Tue 5/20

1:04 pm-5:40 am

1 stop11h 36m

Chicago O'Hare Intl

Tue 6/3

6:00 am-1:34 pm

1 stop12h 34m

$576

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Thu 5/1

1:10 pm-12:07 pm

1 stop17h 57m

Chicago O'Hare Intl

Mon 5/5

7:45 pm-11:55 am

1 stop21h 10m

$641

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Tue 5/20

11:23 am-5:40 am

2 stops13h 17m

Chicago O'Hare Intl

Tue 6/3

6:00 am-10:15 pm

1 stop21h 15m

$659

HiloChicago

ITO - ORD

ITOORD

Hilo Intl

Thu 5/1

6:00 am-11:40 pm

2 stops12h 40m

Chicago O'Hare Intl

Mon 5/5

6:15 am-6:10 pm

2 stops16h 55m

$664

HiloChicago

ITO - ORD

ITOORD

Hilo Intl

Thu 5/1

8:22 am-1:15 pm

2 stops23h 53m

Chicago O'Hare Intl

Mon 5/5

9:05 pm-7:10 pm

2 stops27h 05m

$813

HiloChicago

ITO - ORD

ITOORD

Hilo Intl

Wed 2/12

11:29 am-4:58 pm

2 stops25h 29m

Chicago O'Hare Intl

Sun 2/16

7:00 pm-3:15 pm

2 stops24h 15m

$900

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Sun 3/9

3:55 pm-1:04 pm

2 stops40h 09m

$289

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/28

Showing 1-10 of 23 results
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Best time to book a flight from The Big Island to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from The Big Island 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.

Travel insights for flights from The Big Island to Chicago

Get recent, data-driven insights about flights from The Big Island to Chicago including ideal travel times, pricing trends, and more.

What is the cheapest month to book a flight from The Big Island to Chicago?

Currently, August is the cheapest month in which you can book a flight from The Big Island to Chicago (average of $245). Flying from The Big Island to Chicago in March is currently the most expensive (average of $325). 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 FUI to CHI?

Find hourly flight availability from The Big Island 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 29, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from The Big Island to Chicago as you normally would.

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 January 29, 2025.
Get a feel of what it's like to fly with Southwest, Alaska Airlines and Delta from The Big Island to Chicago by reading reviews from past customers. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,587 reviews

Food

7.1

Overall

8.1

Boarding

8.2

Crew

8.7

Entertainment

7.7

Comfort

8.1

Reviews

1 / 20

6.0
Good

Lauren,Dec 2024

MCI - DCA

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Southwest
8.1
Very good
4,587 reviews
Southwest
8.1
Very good
4,587 reviews

Food

7.1

Overall

8.1

Boarding

8.2

Crew

8.7

Entertainment

7.7

Comfort

8.1

Reviews

1 / 20

6.0
Good

Lauren,Dec 2024

MCI - DCA

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Alaska Airlines
8.0
Very good
9,688 reviews
Southwest
8.1
Very good
4,587 reviews

Food

7.1

Overall

8.1

Boarding

8.2

Crew

8.7

Entertainment

7.7

Comfort

8.1

Reviews

1 / 20

6.0
Good

Lauren,Dec 2024

MCI - DCA

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Delta
8.0
Very good
8,456 reviews
Southwest
8.1
Very good
4,587 reviews

Food

7.1

Overall

8.1

Boarding

8.2

Crew

8.7

Entertainment

7.7

Comfort

8.1

Reviews

1 / 20

6.0
Good

Lauren,Dec 2024

MCI - DCA

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Hawaiian Airlines
7.9
Good
2,321 reviews
Southwest
8.1
Very good
4,587 reviews

Food

7.1

Overall

8.1

Boarding

8.2

Crew

8.7

Entertainment

7.7

Comfort

8.1

Reviews

1 / 20

6.0
Good

Lauren,Dec 2024

MCI - DCA

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

United Airlines
7.4
Good
8,922 reviews
Southwest
8.1
Very good
4,587 reviews

Food

7.1

Overall

8.1

Boarding

8.2

Crew

8.7

Entertainment

7.7

Comfort

8.1

Reviews

1 / 20

6.0
Good

Lauren,Dec 2024

MCI - DCA

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Related info for your journey

Find useful and relevant information for your journey from The Big Island 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 The Big Island to Chicago one-way?

    The cheapest airline one-way is Alaska Airlines, with whom users have recently found tickets for as low as $289. However, be on the lookout for offers from Delta and Southwest, as they are both options that can get you from The Big Island to Chicago for a low price.

  • What are the most popular routes from The Big Island to Chicago?

    When deciding which route to take from The Big Island to Chicago consider Kona Intl - Chicago O'Hare Intl, Kona Intl - Chicago Midway or Hilo Intl - Chicago O'Hare Intl as they are the most popular.

  • What are the cheapest flights from The Big Island to Chicago?

    The cheapest flight price from The Big Island to Chicago is $289. On average you can expect to pay $324. The most popular route, (Kona Intl - Chicago O'Hare Intl), can usually be booked for $461.

  • Can I find deals for flights from The Big Island to Chicago that include hotel bookings?

    Yes. In addition to deals on The Big Island to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from The Big Island to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from The Big Island to Chicago.

  • Can I find deals for business class flights from The Big Island to Chicago?

    Yes. Cheapflights offers flight deals from The Big Island 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 The Big Island to Chicago?

    Currently, August is the cheapest month in which you can book a flight from The Big Island to Chicago (average of $245). Flying from The Big Island to Chicago in March is currently the most expensive (average of $325). 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 The Big Island?

Book flights to The Big Island if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

Browse thousands of different options on Cheapflights for your next trip

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Top 4 airlines flying from The Big Island to Chicago

Discover the top 4 airlines that operate flights from The Big Island 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 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
Alaska AirlinesCheapest$220Average$574FlexibilityNo cancel feeOn-time75%
DeltaCheapest$222Average$491FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$392Average$823FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$399Average$586FlexibilityNo cancel feeOn-time71%
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