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$184+ 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 3/24. Fares are subject to change and may not be available on all flights or dates of travel.
KOA — CHI
Mar 6 — Mar 131
Fri 3/6
Fri 3/13
1 adult, Economy
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Cheap 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 February 4, 2026.

This Delta deal was found by Cheapflights users on 2/3. 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 4/710:15 pm
KOA
-
ORD
2 stops18h 19m
Delta
Sun 4/127:20 am
ORD
-
KOA
1 stop12h 33m
Delta
Deal found 2/3$442
This Kiwi.com deal was found by Cheapflights users on 2/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/1212:10 pm
KOA
-
ORD
1 stop30h 49m
Multiple Airlines
Tue 3/177:40 am
ORD
-
KOA
2 stops32h 28m
Multiple Airlines
Deal found 2/3$490
This Kiwi.com deal was found by Cheapflights users on 2/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/1712:10 pm
KOA
-
ORD
1 stop21h 11m
Multiple Airlines
Mon 3/237:24 pm
ORD
-
KOA
2 stops24h 36m
Multiple Airlines
Deal found 2/3$506
This Alaska Airlines deal was found by Cheapflights users on 2/3. 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 3/1212:10 pm
KOA
-
ORD
1 stop30h 49m
Alaska Airlines
Tue 3/177:00 am
ORD
-
KOA
1 stop14h 13m
Alaska Airlines
Deal found 2/3$512
This Travelocity deal was found by Cheapflights users on 2/3. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/1712:10 pm
KOA
-
ORD
1 stop21h 11m
Alaska Airlines
Mon 3/236:00 am
ORD
-
KOA
1 stop21h 27m
Alaska Airlines
Deal found 2/3$513
This Alaska Airlines deal was found by Cheapflights users on 1/31. 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 2/181:10 pm
KOA
-
ORD
1 stop30h 49m
Multiple Airlines
Sun 2/228:20 am
ORD
-
KOA
2 stops27h 53m
Multiple Airlines
Deal found 1/31$514
This American Airlines deal was found by Cheapflights users on 2/3. 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 2/1111:00 pm
KOA
-
ORD
1 stop11h 53m
American Airlines
Thu 3/59:25 am
ORD
-
KOA
1 stop13h 34m
American Airlines
Deal found 2/3$523
This Alaska Airlines deal was found by Cheapflights users on 2/4. 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 4/78:00 am
KOA
-
ORD
1 stop10h 59m
Alaska Airlines
Sun 4/128:20 am
ORD
-
KOA
1 stop11h 39m
Alaska Airlines
Deal found 2/4$527
This Alaska Airlines deal was found by Cheapflights users on 2/4. 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 4/78:00 am
KOA
-
ORD
1 stop10h 59m
Multiple Airlines
Sun 4/128:20 am
ORD
-
KOA
2 stops17h 06m
Multiple Airlines
Deal found 2/4$533
This Expedia deal was found by Cheapflights users on 2/3. 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.
Wed 2/1110:50 am
KOA
-
ORD
1 stop24h 08m
Multiple Airlines
Thu 3/58:20 am
ORD
-
KOA
2 stops26h 06m
Multiple Airlines
Deal found 2/3$535
This Southwest deal was found by Cheapflights users on 2/3. 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 2/119:25 pm
KOA
-
MDW
1 stop13h 35m
Southwest
Thu 3/55:00 am
MDW
-
KOA
1 stop13h 00m
Southwest
Deal found 2/3$583
This Alaska Airlines deal was found by Cheapflights users on 2/1. 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 2/187:41 pm
ITO
-
ORD
2 stops14h 30m
Multiple Airlines
Sun 2/228:20 am
ORD
-
ITO
2 stops37h 21m
Multiple Airlines
Deal found 2/1$662

Find 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 February 4, 2026.

Round-trip from

$442
(Delta)

One-way from

$184
(Kiwi.com)

Good round-trip deal

$778 or less

Good one-way deal

$319 or less
From The Big Island to Chicago (CHI)
Search Deals
One-way flight from The Big Island to Chicago (CHI)
Search Deals
Price to beat on a round-trip flight from The Big Island to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from The Big Island to Chicago (CHI).
Search Deals

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 February 4, 2026.
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

Tue 4/7

10:15 pm-9:34 pm

2 stops18h 19m

Chicago O'Hare Intl

Sun 4/12

7:20 am-2:53 pm

1 stop12h 33m

$442

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Tue 3/17

12:10 pm-2:21 pm

1 stop21h 11m

Chicago O'Hare Intl

Mon 3/23

7:24 pm-3:00 pm

2 stops24h 36m

$506

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Tue 3/17

12:10 pm-2:21 pm

1 stop21h 11m

Chicago O'Hare Intl

Mon 3/23

6:00 am-10:27 pm

1 stop21h 27m

$513

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Tue 4/7

8:00 am-11:59 pm

1 stop10h 59m

Chicago O'Hare Intl

Sun 4/12

7:59 pm-2:59 pm

1 stop24h 00m

$527

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Tue 4/7

8:00 am-11:59 pm

1 stop10h 59m

Chicago O'Hare Intl

Sun 4/12

8:20 am-7:16 pm

2 stops15h 56m

$533

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Wed 2/18

1:56 pm-1:11 pm

2 stops19h 15m

Chicago O'Hare Intl

Sun 2/22

8:20 am-6:26 am

2 stops26h 06m

$552

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Wed 2/18

6:30 pm-9:45 am

1 stop11h 15m

Chicago O'Hare Intl

Sun 2/22

6:00 am-6:59 pm

1 stop16h 59m

$568

HiloChicago

ITO - ORD

ITOORD

Hilo Intl

Wed 2/18

7:41 pm-2:11 pm

2 stops14h 30m

Chicago O'Hare Intl

Sun 2/22

8:20 am-5:41 pm

2 stops37h 21m

$662

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Tue 2/17

9:25 pm-2:45 pm

2 stops13h 20m

Chicago Midway

Sat 2/21

6:10 am-6:10 pm

2 stops16h 00m

$667

HiloChicago

ITO - ORD

ITOORD

Hilo Intl

Wed 3/25

6:44 pm-11:59 pm

2 stops24h 15m

Chicago O'Hare Intl

Mon 3/30

6:00 am-9:33 pm

2 stops20h 33m

$685

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/3

Showing 1-10 of 45 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, January is the cheapest month in which you can book a flight from The Big Island to Chicago (average of $400). Flying from The Big Island to Chicago in April is currently the most expensive (average of $752). 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 February 4, 2026.

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.

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 February 4, 2026.
Read through reviews of airlines operating flights from The Big Island to Chicago, such as American Airlines. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
American Airlines
7.2
Good
11,222 reviews

Boarding

7.5

Comfort

7.2

Food

6.4

Crew

8.0

Entertainment

6.9

Overall

7.2

Reviews

1 / 20
2.0
Mediocre

Anonymous,Aug 2025

BNA - ORD

My flight was 8 hours delayed, so I missed my connecting flight to Dublin. I understand it’s not the staff’s fault but the lack of sympathy and apology was appalling. I had been sat in the airport since 4am until 3pm and they did not seem understanding. Not good. Need better customer service.
American Airlines
7.2
Good
11,222 reviews
American Airlines
7.2
Good
11,222 reviews

Boarding

7.5

Comfort

7.2

Food

6.4

Crew

8.0

Entertainment

6.9

Overall

7.2

Reviews

1 / 20
2.0
Mediocre

Anonymous,Aug 2025

BNA - ORD

My flight was 8 hours delayed, so I missed my connecting flight to Dublin. I understand it’s not the staff’s fault but the lack of sympathy and apology was appalling. I had been sat in the airport since 4am until 3pm and they did not seem understanding. Not good. Need better customer service.

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.

  • How long is the flight from The Big Island to Chicago?

    Departing from The Big Island to Chicago will take you 13h 20m. The distance from The Big Island to Chicago is about 4213 mi. This flight may include one or multiple stops.

  • 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 $223. However, be on the lookout for offers from Delta and American 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, Hilo Intl - Chicago O'Hare Intl or Kona Intl - Chicago Midway 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 $313. On average you can expect to pay $877. The most popular route, (Kona Intl - Chicago O'Hare Intl), can usually be booked for $442.

  • 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, January is the cheapest month in which you can book a flight from The Big Island to Chicago (average of $400). Flying from The Big Island to Chicago in April is currently the most expensive (average of $752). 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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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 February 4, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$447Average$653FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$447Average$792FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$693Average$768FlexibilityNo cancel feeOn-time63%
Alaska AirlinesCheapest$699Average$979FlexibilityNo cancel feeOn-time75%

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