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$182+ Cheap flights from Chicago (CHI) to The Big Island

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 1/25. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — KOA
Dec 29 — Jan 51
Mon 12/29
Mon 1/5
1 adult, Economy
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Find flight deals from Chicago to The Big Island

Cheapest flights from Chicago to The Big Island
Explore the most affordable flight options available from Chicago to The Big Island. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 29, 2025.

This Delta deal was found by Cheapflights users on 11/28. 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 12/106:00 amORD - KOA
2 stops17h 30mDelta
Sun 12/219:55 pmKOA - ORD
1 stop11h 25mDelta
Deal found 11/28$606
This American Airlines deal was found by Cheapflights users on 11/28. 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.
Fri 12/127:15 amORD - KOA
1 stop11h 57mAmerican Airlines
Fri 12/196:30 pmKOA - ORD
1 stop13h 19mAmerican Airlines
Deal found 11/28$622
This Alaska Airlines deal was found by Cheapflights users on 11/28. 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 12/108:00 amORD - KOA
1 stop13h 22mAlaska Airlines
Sat 12/202:25 pmKOA - ORD
1 stop20h 12mAlaska Airlines
Deal found 11/28$627
This Delta deal was found by Cheapflights users on 11/28. 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.
Sat 12/136:00 amORD - KOA
2 stops17h 30mDelta
Sun 12/219:55 pmKOA - ORD
1 stop11h 25mDelta
Deal found 11/28$635
This Alaska Airlines deal was found by Cheapflights users on 11/28. 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 12/247:00 amORD - KOA
1 stop11h 45mAlaska Airlines
Tue 1/202:51 pmKOA - ORD
1 stop28h 46mAlaska Airlines
Deal found 11/28$651
This Alaska Airlines deal was found by Cheapflights users on 11/28. 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.
Sun 12/148:55 amORD - KOA
1 stop11h 05mAlaska Airlines
Sat 12/202:25 pmKOA - ORD
1 stop20h 12mAlaska Airlines
Deal found 11/28$662
This Alaska Airlines deal was found by Cheapflights users on 11/28. 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 12/108:00 amORD - KOA
1 stop13h 22mAlaska Airlines
Wed 12/172:20 pmKOA - ORD
1 stop25h 42mAlaska Airlines
Deal found 11/28$663
This Alaska Airlines deal was found by Cheapflights users on 11/28. 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.
Sat 12/133:05 pmORD - KOA
1 stop28h 55mAlaska Airlines
Sat 12/202:25 pmKOA - ORD
1 stop20h 12mAlaska Airlines
Deal found 11/28$664
This Alaska Airlines deal was found by Cheapflights users on 11/28. 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.
Thu 12/116:00 amORD - KOA
1 stop12h 40mAlaska Airlines
Sat 12/202:25 pmKOA - ORD
1 stop20h 12mAlaska Airlines
Deal found 11/28$672
This Kiwi.com deal was found by Cheapflights users on 11/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/138:00 amORD - KOA
2 stops40h 29mMultiple Airlines
Sat 12/202:25 pmKOA - ORD
1 stop25h 37mMultiple Airlines
Deal found 11/28$681
This Southwest deal was found by Cheapflights users on 11/25. 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.
Thu 11/275:55 amMDW - KOA
1 stop11h 05mSouthwest
Thu 12/119:15 pmKOA - MDW
1 stop11h 50mSouthwest
Deal found 11/25$683
This Delta deal was found by Cheapflights users on 11/26. 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.
Thu 11/279:41 amMDW - KOA
2 stops13h 44mDelta
Thu 12/41:45 pmKOA - MDW
2 stops16h 09mDelta
Deal found 11/26$694

Cheap flight deals from Chicago to The Big Island

Keep the following information in mind while searching for Chicago to The Big Island flight deals. Data was last updated November 29, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$383
(Delta)

One-way from

$182
(Kiwi.com)

Popular in

December

Cheapest in

September

Average price

$844
Provider with most accurate pricing for Chicago (CHI)-Kona Intl flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Kona Intl flights.
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From Chicago (CHI) to The Big Island
Search Deals
One-way flight from Chicago (CHI) to The Big Island
Search Deals
Highest demand for flights based on searches. 12% potential increase in price ($104 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($34 potential savings vs. average RT price).
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Average for round-trip flights in November 2025
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Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to The Big Island 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 November 29, 2025.
Use the filters below to find and compare flights from Chicago to The Big Island that are best for you.

Fly from

Chicago

Fly to

The Big Island

Route

Depart

Return

Price

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Sun 2/1

7:30 am-6:30 pm

2 stops15h 00m

Kona Intl

Wed 2/11

9:55 pm-1:22 pm

1 stop11h 27m

$389

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Wed 1/21

7:30 am-6:30 pm

2 stops15h 00m

Kona Intl

Tue 1/27

8:45 pm-1:22 pm

1 stop12h 37m

$389

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Wed 2/25

3:07 pm-12:53 pm

2 stops25h 46m

Kona Intl

Tue 3/3

9:01 pm-2:58 pm

2 stops13h 57m

$395

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Wed 1/21

8:00 am-9:30 pm

1 stop17h 30m

Kona Intl

Tue 1/27

2:51 pm-11:37 pm

1 stop28h 46m

$403

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Tue 2/3

7:30 am-6:30 pm

2 stops15h 00m

Kona Intl

Fri 2/13

8:59 pm-4:41 pm

2 stops15h 42m

$404

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Mon 2/2

3:35 pm-9:30 pm

1 stop33h 55m

Kona Intl

Wed 2/4

2:51 pm-2:29 pm

1 stop19h 38m

$413

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

Wed 2/25

9:34 am-7:34 pm

2 stops14h 00m

Kona Intl

Tue 3/3

8:59 pm-5:37 pm

2 stops16h 38m

$414

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Sun 2/1

3:44 pm-10:32 am

2 stops22h 48m

Kona Intl

Wed 2/11

6:00 am-11:37 pm

2 stops13h 37m

$415

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Thu 2/19

5:29 pm-10:57 pm

1 stop33h 28m

Kona Intl

Thu 2/26

7:50 pm-11:59 pm

2 stops24h 09m

$419

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Sun 1/11

7:30 am-6:47 pm

1 stop15h 17m

Kona Intl

Sat 1/17

8:45 pm-11:53 pm

1 stop23h 08m

$421

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/26

Showing 1-10 of 60 results
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Best time to book a flight from Chicago to The Big Island

Have a flexible travel schedule? Discover the best time to fly to The Big Island from Chicago 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 Chicago to The Big Island

What is the cheapest month to book a flight from Chicago to The Big Island?

Currently, September is the cheapest month in which you can book a flight from Chicago to The Big Island (average of $423). Flying from Chicago to The Big Island in July is currently the most expensive (average of $667). 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 CHI to FUI?

Find hourly flight availability from Chicago to The Big Island. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated November 29, 2025.

When flying from Chicago to The Big Island, the time of day you fly usually plays a role in the price. Save by searching for a flight at noon, which can drop the price by up to 31% versus a flight in the evening.

Reviews of airlines servicing The Big Island

Get insights into the airlines that provide service to The Big Island. 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 The Big Island. Reviews last updated November 29, 2025.
Read reviews from past customers who have flown Alaska Airlines, Southwest, and Delta from Chicago to The Big Island. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
11,376 reviews

Entertainment

7.0

Crew

8.5

Food

7.1

Overall

8.0

Boarding

8.1

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

Christine,Nov 2025

MIA - PDX

Just got on, logged in, and zoned out on some TV sit calm. Flight was easy Miami airport is something else!!! what a mess and now that I think of it, the luggage desk staff was super slow, I began to get irritated over paper running out, TSA was at the the end of the desk and the agent was assuring us we would get on flight, we arrived early, just didn't find the Alaska desk due to miss information. We walked that airport back and forth 3times. Language barriers were part of that fiasco and searching for American Airlines didn't help. (rolling my eyes)
Alaska Airlines
8.0
Very good
11,376 reviews
Alaska Airlines
8.0
Very good
11,376 reviews

Entertainment

7.0

Crew

8.5

Food

7.1

Overall

8.0

Boarding

8.1

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

Christine,Nov 2025

MIA - PDX

Just got on, logged in, and zoned out on some TV sit calm. Flight was easy Miami airport is something else!!! what a mess and now that I think of it, the luggage desk staff was super slow, I began to get irritated over paper running out, TSA was at the the end of the desk and the agent was assuring us we would get on flight, we arrived early, just didn't find the Alaska desk due to miss information. We walked that airport back and forth 3times. Language barriers were part of that fiasco and searching for American Airlines didn't help. (rolling my eyes)
Southwest
8.0
Very good
4,255 reviews
Alaska Airlines
8.0
Very good
11,376 reviews

Entertainment

7.0

Crew

8.5

Food

7.1

Overall

8.0

Boarding

8.1

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

Christine,Nov 2025

MIA - PDX

Just got on, logged in, and zoned out on some TV sit calm. Flight was easy Miami airport is something else!!! what a mess and now that I think of it, the luggage desk staff was super slow, I began to get irritated over paper running out, TSA was at the the end of the desk and the agent was assuring us we would get on flight, we arrived early, just didn't find the Alaska desk due to miss information. We walked that airport back and forth 3times. Language barriers were part of that fiasco and searching for American Airlines didn't help. (rolling my eyes)
Delta
7.9
Good
8,012 reviews
Alaska Airlines
8.0
Very good
11,376 reviews

Entertainment

7.0

Crew

8.5

Food

7.1

Overall

8.0

Boarding

8.1

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

Christine,Nov 2025

MIA - PDX

Just got on, logged in, and zoned out on some TV sit calm. Flight was easy Miami airport is something else!!! what a mess and now that I think of it, the luggage desk staff was super slow, I began to get irritated over paper running out, TSA was at the the end of the desk and the agent was assuring us we would get on flight, we arrived early, just didn't find the Alaska desk due to miss information. We walked that airport back and forth 3times. Language barriers were part of that fiasco and searching for American Airlines didn't help. (rolling my eyes)
United Airlines
7.4
Good
9,059 reviews
Alaska Airlines
8.0
Very good
11,376 reviews

Entertainment

7.0

Crew

8.5

Food

7.1

Overall

8.0

Boarding

8.1

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

Christine,Nov 2025

MIA - PDX

Just got on, logged in, and zoned out on some TV sit calm. Flight was easy Miami airport is something else!!! what a mess and now that I think of it, the luggage desk staff was super slow, I began to get irritated over paper running out, TSA was at the the end of the desk and the agent was assuring us we would get on flight, we arrived early, just didn't find the Alaska desk due to miss information. We walked that airport back and forth 3times. Language barriers were part of that fiasco and searching for American Airlines didn't help. (rolling my eyes)
American Airlines
7.2
Good
11,044 reviews
Alaska Airlines
8.0
Very good
11,376 reviews

Entertainment

7.0

Crew

8.5

Food

7.1

Overall

8.0

Boarding

8.1

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

Christine,Nov 2025

MIA - PDX

Just got on, logged in, and zoned out on some TV sit calm. Flight was easy Miami airport is something else!!! what a mess and now that I think of it, the luggage desk staff was super slow, I began to get irritated over paper running out, TSA was at the the end of the desk and the agent was assuring us we would get on flight, we arrived early, just didn't find the Alaska desk due to miss information. We walked that airport back and forth 3times. Language barriers were part of that fiasco and searching for American Airlines didn't help. (rolling my eyes)

Related info for your journey

Find useful and relevant information for your journey from Chicago to The Big Island. 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 Chicago to The Big Island?

    Departing from Chicago to The Big Island will take you 11h 35m. Chicago and The Big Island are separated by a distance of 4213 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the cheapest airlines to fly from Chicago to The Big Island one-way?

    $198 is the cheapest one-way deal found within the past few days, from Alaska Airlines. You may also be able to find cheap deals on Southwest and Delta, with prices starting from $342 and $347, respectively.

  • What are the most popular routes from Chicago to The Big Island?

    The most popular flight routes from Chicago to The Big Island are Chicago O'Hare Intl - Kona Intl, Chicago Midway - Kona Intl and Chicago O'Hare Intl - Hilo Intl.

  • Can I find deals for flights from Chicago to The Big Island that include hotel bookings?

    Yes. In addition to deals on Chicago to The Big Island flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to The Big Island?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to The Big Island.

  • Can I find deals for business class flights from Chicago to The Big Island?

    Yes. Cheapflights offers flight deals from Chicago to The Big Island 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 Chicago to The Big Island?

    Currently, September is the cheapest month in which you can book a flight from Chicago to The Big Island (average of $423). Flying from Chicago to The Big Island in July is currently the most expensive (average of $667). 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

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Alternative routes for Chicago to The Big Island

See prices for flight routes from nearby airports that may be better suited for you.
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Top 6 airlines flying from Chicago to The Big Island

Discover the top 6 airlines that operate flights from Chicago to The Big Island. 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 November 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$371Average$609FlexibilityNo cancel feeOn-timeN/A
Alaska AirlinesCheapest$429Average$707FlexibilityNo cancel feeOn-time75%
Hawaiian AirlinesCheapest$429Average$651FlexibilityNo cancel feeOn-time85%
United AirlinesCheapest$447Average$1,014FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$459Average$729FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$593Average$722FlexibilityNo cancel feeOn-time63%

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