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$247+ 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 9/6. Fares are subject to change and may not be available on all flights or dates of travel.
KOA — CHI
Apr 30 — May 71
Wed 4/30
Wed 5/7
1 adult, Economy
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Cheap flight deals from The Big Island to Chicago

Keep the following information in mind while searching for The Big Island to Chicago flight deals. Data was last updated April 25, 2025.

Round-trip from

$498
(Delta)

One-way from

$247
(Delta)

Good one-way deal

$594 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 April 25, 2025.

This Delta deal was found by Cheapflights users on 4/23. 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 8/259:45 pmKOA - ORD
1 stop10h 39mDelta
Sun 8/316:50 amORD - KOA
2 stops15h 48mDelta
Deal found 4/23$498
This Delta deal was found by Cheapflights users on 4/25. 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.
Fri 8/299:45 pmKOA - MDW
2 stops33h 45mDelta
Tue 9/99:20 amMDW - KOA
2 stops14h 20mDelta
Deal found 4/25$530
This Alaska Airlines deal was found by Cheapflights users on 4/24. 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.
Tue 5/206:00 pmKOA - ORD
2 stops15h 18mAlaska Airlines
Tue 6/37:51 pmORD - KOA
1 stop31h 24mAlaska Airlines
Deal found 4/24$573
This American Airlines deal was found by Cheapflights users on 4/24. 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 6/139:25 pmKOA - ORD
1 stop10h 17mAmerican Airlines
Tue 7/226:13 amORD - KOA
1 stop12h 50mAmerican Airlines
Deal found 4/24$632
This Southwest deal was found by Cheapflights users on 4/25. 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.
Fri 8/299:15 amKOA - MDW
2 stops14h 55mSouthwest
Sat 9/66:20 amMDW - KOA
1 stop10h 50mSouthwest
Deal found 4/25$686
This United Airlines deal was found by Cheapflights users on 4/24. 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.
Sat 5/3112:58 pmKOA - ORD
1 stop18h 44mUnited Airlines
Sun 6/17:40 pmORD - KOA
1 stop29h 23mUnited Airlines
Deal found 4/24$826
This Delta deal was found by Cheapflights users on 4/24. 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 4/3011:35 amITO - ORD
2 stops15h 20mDelta
Thu 5/157:10 amORD - ITO
2 stops16h 59mDelta
Deal found 4/24$894
This Alaska Airlines deal was found by Cheapflights users on 4/25. 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 5/106:30 pmITO - ORD
2 stops15h 43mAlaska Airlines
Wed 5/146:00 amORD - ITO
2 stops17h 00mAlaska Airlines
Deal found 4/25$929
This United Airlines deal was found by Cheapflights users on 4/24. 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.
Sun 6/84:16 pmITO - ORD
2 stops27h 43mUnited Airlines
Sun 6/159:30 amORD - ITO
1 stop27h 37mUnited Airlines
Deal found 4/24$1,004

Cheapflights Fare Finder

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 April 25, 2025.
Use the filters below to find and compare flights from The Big Island to Chicago that are best for you.

Fly from

The Big Island

Fly to

Chicago

Route

Depart

Return

Price

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Mon 8/25

9:45 pm-1:24 pm

1 stop10h 39m

Chicago O'Hare Intl

Sun 8/31

6:50 am-5:38 pm

2 stops15h 48m

$498

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Fri 8/29

9:45 pm-12:30 pm

2 stops33h 45m

Chicago Midway

Mon 9/8

9:20 am-6:40 pm

2 stops14h 20m

$530

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Tue 5/20

6:00 pm-2:18 pm

2 stops15h 18m

Chicago O'Hare Intl

Tue 6/3

7:51 pm-10:15 pm

1 stop31h 24m

$573

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Fri 6/13

9:25 pm-12:42 pm

1 stop10h 17m

Chicago O'Hare Intl

Tue 7/22

6:13 am-2:03 pm

1 stop12h 50m

$632

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Fri 8/29

9:15 am-5:10 am

2 stops14h 55m

Chicago Midway

Sat 9/6

6:20 am-12:10 pm

1 stop10h 50m

$686

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Sat 5/31

12:58 pm-12:42 pm

1 stop18h 44m

Chicago O'Hare Intl

Sun 6/1

7:40 pm-8:03 pm

1 stop29h 23m

$826

HiloChicago

ITO - ORD

ITOORD

Hilo Intl

Sat 5/10

6:30 pm-3:13 pm

2 stops15h 43m

Chicago O'Hare Intl

Wed 5/14

6:00 am-6:00 pm

2 stops17h 00m

$929

HiloChicago

ITO - ORD

ITOORD

Hilo Intl

Mon 7/21

7:00 pm-5:50 pm

2 stops17h 50m

Chicago O'Hare Intl

Mon 7/28

7:00 am-6:29 pm

2 stops16h 29m

$933

HiloChicago

ITO - ORD

ITOORD

Hilo Intl

Sun 6/8

4:16 pm-12:59 am

2 stops27h 43m

Chicago O'Hare Intl

Sun 6/15

9:30 am-8:07 am

1 stop27h 37m

$1,004

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Sat 9/6

9:45 pm-1:24 pm

1 stop10h 39m

$247

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/23

Showing 1-10 of 18 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.

Cheapflights Insights

Everything you need to know about your flight from The Big Island to Chicago

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 $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 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 April 25, 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 April 25, 2025.
Get a feel of what it's like to fly with Alaska Airlines, Southwest 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.
Alaska Airlines
8.0
Very good
9,928 reviews

Food

7.1

Crew

8.5

Entertainment

7.1

Comfort

7.9

Overall

8.0

Boarding

8.2

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
9,928 reviews
Alaska Airlines
8.0
Very good
9,928 reviews

Food

7.1

Crew

8.5

Entertainment

7.1

Comfort

7.9

Overall

8.0

Boarding

8.2

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
4,287 reviews
Alaska Airlines
8.0
Very good
9,928 reviews

Food

7.1

Crew

8.5

Entertainment

7.1

Comfort

7.9

Overall

8.0

Boarding

8.2

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
7,920 reviews
Alaska Airlines
8.0
Very good
9,928 reviews

Food

7.1

Crew

8.5

Entertainment

7.1

Comfort

7.9

Overall

8.0

Boarding

8.2

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
2,395 reviews
Alaska Airlines
8.0
Very good
9,928 reviews

Food

7.1

Crew

8.5

Entertainment

7.1

Comfort

7.9

Overall

8.0

Boarding

8.2

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
8,685 reviews
Alaska Airlines
8.0
Very good
9,928 reviews

Food

7.1

Crew

8.5

Entertainment

7.1

Comfort

7.9

Overall

8.0

Boarding

8.2

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 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 Delta, with whom users have recently found tickets for as low as $247. However, be on the lookout for offers from American Airlines and Alaska Airlines, 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 $543. On average you can expect to pay $760. The most popular route, (Kona Intl - Chicago O'Hare Intl), can usually be booked for $498.

  • 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 $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 The Big Island?

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

Browse thousands of different options on Cheapflights for your next trip

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Top 5 airlines flying from The Big Island to Chicago

Discover the top 5 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 April 25, 2025.
AirlineCheapestAverageFlexibilityOn-time
Alaska AirlinesCheapest$220Average$574FlexibilityNo cancel feeOn-time75%
DeltaCheapest$222Average$511FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$392Average$802FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$399Average$615FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$701Average$768FlexibilityNo cancel feeOn-time63%

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