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$231+ 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 9/10. Fares are subject to change and may not be available on all flights or dates of travel.
KOA — CHI
Jun 22 — Jun 291
Sun 6/22
Sun 6/29
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 June 17, 2025.

Round-trip from

$437
(Alaska Airlines)

One-way from

$231
(Alaska Airlines)
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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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 June 17, 2025.

This Alaska Airlines deal was found by Cheapflights users on 6/16. 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.
Mon 9/158:36 amITO - ORD
2 stops17h 27mAlaska Airlines
Tue 9/1610:00 amORD - ITO
2 stops15h 30mAlaska Airlines
Deal found 6/16$437
This American Airlines deal was found by Cheapflights users on 6/16. 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 10/43:13 pmKOA - ORD
1 stop21h 43mAmerican Airlines
Mon 11/37:10 amORD - KOA
1 stop11h 54mAmerican Airlines
Deal found 6/16$522
This Alaska Airlines deal was found by Cheapflights users on 6/16. 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.
Sat 10/49:20 pmKOA - ORD
1 stop21h 39mAlaska Airlines
Mon 11/39:20 amORD - KOA
2 stops15h 06mAlaska Airlines
Deal found 6/16$542
This Delta deal was found by Cheapflights users on 6/16. 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.
Wed 7/309:47 pmKOA - ORD
1 stop14h 33mDelta
Wed 8/66:00 amORD - KOA
2 stops18h 00mDelta
Deal found 6/16$656
This Southwest deal was found by Cheapflights users on 6/15. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/166:00 amITO - ORD
2 stops12h 40mSouthwest
Wed 9/106:15 amORD - ITO
2 stops16h 55mSouthwest
Deal found 6/15$694
This Southwest deal was found by Cheapflights users on 6/16. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/77:00 pmKOA - MDW
2 stops13h 25mSouthwest
Wed 8/136:10 amMDW - KOA
1 stop11h 00mSouthwest
Deal found 6/16$743
This Trip.com deal was found by Cheapflights users on 6/15. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/306:00 amITO - ORD
2 stops19h 03mMultiple Airlines
Wed 8/67:08 amORD - ITO
2 stops28h 52mMultiple Airlines
Deal found 6/15$785
This United Airlines deal was found by Cheapflights users on 6/15. 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.
Mon 6/301:15 pmKOA - ORD
2 stops18h 54mUnited Airlines
Fri 7/46:20 pmORD - KOA
2 stops22h 40mUnited Airlines
Deal found 6/15$935
This United Airlines deal was found by Cheapflights users on 6/15. 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 7/25:25 pmITO - ORD
1 stop31h 54mUnited Airlines
Wed 9/108:50 amORD - ITO
2 stops37h 49mUnited Airlines
Deal found 6/15$989
This Delta deal was found by Cheapflights users on 6/15. 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.
Tue 7/88:35 pmKOA - MDW
2 stops16h 04mDelta
Mon 7/149:24 amMDW - KOA
2 stops14h 36mDelta
Deal found 6/15$1,109
This Hawaiian Airlines deal was found by Cheapflights users on 6/15. 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 Hawaiian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/168:00 amKOA - ORD
1 stop10h 59mHawaiian Airlines
Mon 6/236:00 amORD - KOA
1 stop12h 40mHawaiian Airlines
Deal found 6/15$2,834

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 June 17, 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

HiloChicago

ITO - ORD

ITOORD

Hilo Intl

Mon 9/15

8:36 am-7:03 am

2 stops17h 27m

Chicago O'Hare Intl

Tue 9/16

10:00 am-8:30 pm

2 stops15h 30m

$437

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Sat 10/4

3:13 pm-5:56 pm

1 stop21h 43m

Chicago O'Hare Intl

Mon 11/3

7:10 am-3:04 pm

1 stop11h 54m

$522

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Sat 10/4

9:20 pm-11:59 pm

1 stop21h 39m

Chicago O'Hare Intl

Mon 11/3

9:20 am-8:26 pm

2 stops15h 06m

$542

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Wed 7/30

9:47 pm-5:20 pm

1 stop14h 33m

Chicago O'Hare Intl

Wed 8/6

6:00 am-7:00 pm

2 stops18h 00m

$656

HiloChicago

ITO - ORD

ITOORD

Hilo Intl

Wed 7/16

6:00 am-11:40 pm

2 stops12h 40m

Chicago O'Hare Intl

Wed 9/10

6:15 am-6:10 pm

2 stops16h 55m

$694

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Thu 8/7

7:00 pm-1:25 pm

2 stops13h 25m

Chicago Midway

Wed 8/13

6:10 am-12:10 pm

1 stop11h 00m

$743

HiloChicago

ITO - ORD

ITOORD

Hilo Intl

Wed 7/30

6:00 am-6:03 am

2 stops19h 03m

Chicago O'Hare Intl

Wed 8/6

7:08 am-7:00 am

2 stops28h 52m

$785

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Mon 6/30

1:15 pm-1:09 pm

2 stops18h 54m

Chicago O'Hare Intl

Fri 7/4

6:20 pm-12:00 pm

2 stops22h 40m

$935

HiloChicago

ITO - ORD

ITOORD

Hilo Intl

Wed 7/2

5:25 pm-6:19 am

1 stop31h 54m

Chicago O'Hare Intl

Wed 9/10

8:50 am-5:39 pm

2 stops37h 49m

$989

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Tue 7/8

8:35 pm-5:39 pm

2 stops16h 04m

Chicago Midway

Mon 7/14

9:24 am-7:00 pm

2 stops14h 36m

$1,109

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/16

Showing 1-10 of 19 results
1
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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 June 17, 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 June 17, 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
10,000 reviews

Comfort

7.8

Boarding

8.1

Entertainment

7.1

Overall

8.0

Food

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Boarding

8.1

Entertainment

7.1

Overall

8.0

Food

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Southwest
8.0
Very good
4,279 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Boarding

8.1

Entertainment

7.1

Overall

8.0

Food

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Delta
8.0
Very good
7,963 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Boarding

8.1

Entertainment

7.1

Overall

8.0

Food

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
United Airlines
7.4
Good
8,801 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Boarding

8.1

Entertainment

7.1

Overall

8.0

Food

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
American Airlines
7.2
Good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Boarding

8.1

Entertainment

7.1

Overall

8.0

Food

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

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 $231. 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.

  • 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
Lansing
Benton Harbor
Porter
Hammond
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 June 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$223Average$603FlexibilityNo cancel feeOn-timeN/A
Alaska AirlinesCheapest$394Average$816FlexibilityNo cancel feeOn-time75%
American AirlinesCheapest$419Average$623FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$429Average$865FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$713Average$768FlexibilityNo cancel feeOn-time63%

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