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$299+ 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 5/9. Fares are subject to change and may not be available on all flights or dates of travel.
KOA — CHI
Apr 9 — Apr 161
Wed 4/9
Wed 4/16
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 4, 2025.

Round-trip from

$557
(Alaska Airlines)

One-way from

$299
(Alaska Airlines)

Good round-trip deal

$1,221 or less

Good one-way deal

$760 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 round-trip 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 4, 2025.

This Alaska Airlines deal was found by Cheapflights users on 4/3. 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.
Tue 5/209:44 pmKOA - ORD
1 stop19h 39mAlaska Airlines
Tue 6/37:51 pmORD - KOA
1 stop31h 24mAlaska Airlines
Deal found 4/3$557
This Delta deal was found by Cheapflights users on 4/3. 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 5/209:39 pmKOA - ORD
1 stop10h 51mDelta
Tue 6/36:24 amORD - KOA
2 stops17h 46mDelta
Deal found 4/3$562
This Delta deal was found by Cheapflights users on 4/3. 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.
Wed 5/219:39 pmKOA - MDW
2 stops16h 06mDelta
Tue 6/39:20 amMDW - KOA
2 stops14h 50mDelta
Deal found 4/3$618
This American Airlines deal was found by Cheapflights users on 4/3. 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.
Fri 6/139:25 pmKOA - ORD
1 stop10h 17mAmerican Airlines
Tue 7/226:13 amORD - KOA
1 stop12h 50mAmerican Airlines
Deal found 4/3$685
This Southwest deal was found by Cheapflights users on 4/3. 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.
Sat 7/1911:20 amKOA - MDW
1 stop12h 40mSouthwest
Wed 7/238:05 amMDW - KOA
2 stops14h 50mSouthwest
Deal found 4/3$813
This United Airlines deal was found by Cheapflights users on 4/3. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/181:09 pmKOA - ORD
1 stop29h 32mUnited Airlines
Tue 4/223:50 pmORD - KOA
1 stop25h 04mUnited Airlines
Deal found 4/3$823
This Alaska Airlines deal was found by Cheapflights users on 4/3. 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.
Sun 11/28:37 amITO - ORD
2 stops16h 27mAlaska Airlines
Sun 11/97:00 amORD - ITO
2 stops19h 14mAlaska Airlines
Deal found 4/3$852
This Southwest deal was found by Cheapflights users on 4/3. 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.
Sat 7/198:20 pmKOA - ORD
2 stops13h 40mSouthwest
Wed 7/236:15 amORD - KOA
2 stops16h 40mSouthwest
Deal found 4/3$919
This United deal was found by Cheapflights users on 4/3. 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 United is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/308:25 amITO - ORD
2 stops22h 01mUnited Airlines
Thu 5/159:30 amORD - ITO
1 stop15h 38mUnited Airlines
Deal found 4/3$925
This American Airlines deal was found by Cheapflights users on 4/3. 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.
Sun 11/27:29 amITO - ORD
1 stop19h 41mMultiple Airlines
Sun 11/99:45 amORD - ITO
1 stop12h 33mMultiple Airlines
Deal found 4/3$1,341

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 4, 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

Tue 5/20

9:44 pm-10:23 pm

1 stop19h 39m

Chicago O'Hare Intl

Tue 6/3

7:51 pm-10:15 pm

1 stop31h 24m

$557

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Tue 5/20

9:39 pm-1:30 pm

1 stop10h 51m

Chicago O'Hare Intl

Tue 6/3

6:24 am-7:10 pm

2 stops17h 46m

$562

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Wed 5/21

9:39 pm-6:45 pm

2 stops16h 06m

Chicago Midway

Tue 6/3

9:20 am-7:10 pm

2 stops14h 50m

$618

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

$685

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Sat 7/19

11:20 am-5:00 am

1 stop12h 40m

Chicago Midway

Wed 7/23

8:05 am-5:55 pm

2 stops14h 50m

$813

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Fri 4/18

1:09 pm-11:41 pm

1 stop29h 32m

Chicago O'Hare Intl

Tue 4/22

3:50 pm-11:54 am

1 stop25h 04m

$823

HiloChicago

ITO - ORD

ITOORD

Hilo Intl

Wed 4/30

3:05 pm-5:00 pm

2 stops20h 55m

Chicago O'Hare Intl

Thu 5/15

10:00 am-7:02 am

2 stops26h 02m

$908

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Sat 7/19

8:20 pm-3:00 pm

2 stops13h 40m

Chicago O'Hare Intl

Wed 7/23

6:15 am-5:55 pm

2 stops16h 40m

$919

HiloChicago

ITO - ORD

ITOORD

Hilo Intl

Wed 4/30

8:25 am-11:26 am

2 stops22h 01m

Chicago O'Hare Intl

Thu 5/15

9:30 am-8:08 pm

1 stop15h 38m

$925

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Fri 5/9

8:46 am-2:48 pm

2 stops25h 02m

$299

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/3

Showing 1-10 of 20 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 4, 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 4, 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
9,836 reviews

Comfort

7.9

Entertainment

7.1

Overall

8.0

Crew

8.5

Food

7.1

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Alaska Airlines
8.0
Very good
9,836 reviews
Alaska Airlines
8.0
Very good
9,836 reviews

Comfort

7.9

Entertainment

7.1

Overall

8.0

Crew

8.5

Food

7.1

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Southwest
8.0
Very good
4,276 reviews
Alaska Airlines
8.0
Very good
9,836 reviews

Comfort

7.9

Entertainment

7.1

Overall

8.0

Crew

8.5

Food

7.1

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Delta
8.0
Very good
7,897 reviews
Alaska Airlines
8.0
Very good
9,836 reviews

Comfort

7.9

Entertainment

7.1

Overall

8.0

Crew

8.5

Food

7.1

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Hawaiian Airlines
7.9
Good
2,347 reviews
Alaska Airlines
8.0
Very good
9,836 reviews

Comfort

7.9

Entertainment

7.1

Overall

8.0

Crew

8.5

Food

7.1

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
United Airlines
7.4
Good
8,618 reviews
Alaska Airlines
8.0
Very good
9,836 reviews

Comfort

7.9

Entertainment

7.1

Overall

8.0

Crew

8.5

Food

7.1

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

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 $299. However, be on the lookout for offers from American Airlines and Delta, 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 $708. On average you can expect to pay $1,014. The most popular route, (Kona Intl - Chicago O'Hare Intl), can usually be booked for $562.

  • 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
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 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 4, 2025.
AirlineCheapestAverageFlexibilityOn-time
Alaska AirlinesCheapest$220Average$574FlexibilityNo cancel feeOn-time75%
DeltaCheapest$222Average$511FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$392Average$823FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$399Average$615FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$701Average$768FlexibilityNo cancel feeOn-time63%

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