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$234+ 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 9/3. Fares are subject to change and may not be available on all flights or dates of travel.
KOA — CHI
May 5 — May 121
Mon 5/5
Mon 5/12
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 30, 2025.

Round-trip from

$467
(Alaska Airlines)

One-way from

$234
(Alaska Airlines)

Good one-way deal

$375 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 30, 2025.

This Alaska Airlines deal was found by Cheapflights users on 4/28. 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 9/38:00 amKOA - ORD
1 stop10h 59mAlaska Airlines
Sun 9/76:20 amORD - KOA
1 stop14h 35mAlaska Airlines
Deal found 4/28$467
This Delta deal was found by Cheapflights users on 4/28. 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.
Wed 9/39:45 pmKOA - ORD
2 stops15h 20mDelta
Sun 9/76:00 amORD - KOA
2 stops17h 25mDelta
Deal found 4/28$478
This American Airlines deal was found by Cheapflights users on 4/28. 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.
Wed 8/139:40 pmKOA - ORD
1 stop13h 14mAmerican Airlines
Wed 8/207:00 amORD - KOA
1 stop11h 29mAmerican Airlines
Deal found 4/28$545
This Delta deal was found by Cheapflights users on 4/28. 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.
Wed 9/39:45 pmKOA - MDW
2 stops15h 18mDelta
Sun 9/79:20 amMDW - KOA
2 stops14h 05mDelta
Deal found 4/28$546
This Southwest deal was found by Cheapflights users on 4/28. 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.
Wed 9/38:30 pmKOA - MDW
1 stop13h 00mSouthwest
Sun 9/75:15 amMDW - KOA
2 stops12h 50mSouthwest
Deal found 4/28$553
This Alaska Airlines deal was found by Cheapflights users on 4/29. 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 4/303:05 pmITO - ORD
2 stops21h 56mAlaska Airlines
Thu 5/156:00 amORD - ITO
2 stops16h 57mAlaska Airlines
Deal found 4/29$1,002
This United Airlines deal was found by Cheapflights users on 4/29. 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 4/308:25 amITO - ORD
2 stops17h 05mUnited Airlines
Thu 5/159:30 amORD - ITO
1 stop14h 39mUnited Airlines
Deal found 4/29$1,056

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 30, 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

Wed 9/3

8:00 am-11:59 pm

1 stop10h 59m

Chicago O'Hare Intl

Sun 9/7

6:20 am-3:55 pm

1 stop14h 35m

$467

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Wed 9/3

9:45 pm-6:05 pm

2 stops15h 20m

Chicago O'Hare Intl

Sun 9/7

6:00 am-6:25 pm

2 stops17h 25m

$478

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Wed 8/13

9:40 pm-3:54 pm

1 stop13h 14m

Chicago O'Hare Intl

Wed 8/20

7:00 am-1:29 pm

1 stop11h 29m

$545

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Wed 9/3

9:45 pm-6:03 pm

2 stops15h 18m

Chicago Midway

Sun 9/7

9:20 am-6:25 pm

2 stops14h 05m

$546

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Wed 9/3

8:30 pm-2:30 pm

1 stop13h 00m

Chicago Midway

Sun 9/7

5:15 am-1:05 pm

2 stops12h 50m

$553

HiloChicago

ITO - ORD

ITOORD

Hilo Intl

Fri 6/13

8:36 am-11:39 pm

2 stops34h 03m

Chicago O'Hare Intl

Sat 7/19

3:09 pm-7:00 am

2 stops20h 51m

$1,140

HiloChicago

ITO - ORD

ITOORD

Hilo Intl

Fri 6/13

7:49 am-6:19 am

1 stop17h 30m

Chicago O'Hare Intl

Sat 7/19

9:30 am-6:29 pm

1 stop13h 59m

$1,639

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Wed 9/3

8:00 am-11:59 pm

1 stop10h 59m

$234

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Wed 9/3

9:45 pm-6:03 pm

2 stops15h 18m

$239

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Wed 9/3

9:45 pm-6:05 pm

2 stops15h 20m

$239

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/28

Showing 1-10 of 15 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 April 30, 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 30, 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
9,961 reviews

Comfort

7.9

Food

7.1

Crew

8.5

Overall

8.0

Entertainment

7.1

Boarding

8.2

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
9,961 reviews
Alaska Airlines
8.0
Very good
9,961 reviews

Comfort

7.9

Food

7.1

Crew

8.5

Overall

8.0

Entertainment

7.1

Boarding

8.2

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
4,295 reviews
Alaska Airlines
8.0
Very good
9,961 reviews

Comfort

7.9

Food

7.1

Crew

8.5

Overall

8.0

Entertainment

7.1

Boarding

8.2

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
7,929 reviews
Alaska Airlines
8.0
Very good
9,961 reviews

Comfort

7.9

Food

7.1

Crew

8.5

Overall

8.0

Entertainment

7.1

Boarding

8.2

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
8,696 reviews
Alaska Airlines
8.0
Very good
9,961 reviews

Comfort

7.9

Food

7.1

Crew

8.5

Overall

8.0

Entertainment

7.1

Boarding

8.2

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
9,961 reviews

Comfort

7.9

Food

7.1

Crew

8.5

Overall

8.0

Entertainment

7.1

Boarding

8.2

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 $234. 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, 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 $370. On average you can expect to pay $594. The most popular route, (Kona Intl - Chicago O'Hare Intl), can usually be booked for $467.

  • 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

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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 30, 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$617FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$701Average$768FlexibilityNo cancel feeOn-time63%

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