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Cheap flights from The Big Island to Chicago (CHI)

KOA — CHI
Aug 17 — Aug 241
Mon 8/17
Mon 8/24
1 adult, Economy
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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 July 18, 2026.

Round-trip from

$445
(Alaska Airlines)

One-way from

$277
(Southwest)

Good round-trip deal

$778 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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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, February is the cheapest month in which you can book a flight from The Big Island to Chicago (average of $422). Flying from The Big Island to Chicago in May is currently the most expensive (average of $1,264). 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.

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 July 18, 2026.
Read through reviews of airlines operating flights from The Big Island to Chicago, such as United 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.
United Airlines
7.4
Good
10,006 reviews

Comfort

7.3

Food

6.6

Entertainment

7.1

Crew

8.1

Overall

7.4

Boarding

7.7

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!
United Airlines
7.4
Good
10,006 reviews
United Airlines
7.4
Good
10,006 reviews

Comfort

7.3

Food

6.6

Entertainment

7.1

Crew

8.1

Overall

7.4

Boarding

7.7

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!

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 12h 02m. The distance from The Big Island to Chicago is about 4205 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 American Airlines, with whom users have recently found tickets for as low as $211. However, be on the lookout for offers from Alaska Airlines 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 Hilo Intl - Chicago O'Hare Intl, Kona 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 $334. On average you can expect to pay $1,394. The most popular route, (Hilo Intl - Chicago O'Hare Intl), can usually be booked for $545.

  • 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, February is the cheapest month in which you can book a flight from The Big Island to Chicago (average of $422). Flying from The Big Island to Chicago in May is currently the most expensive (average of $1,264). 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
Benton Harbor
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter

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Top 2 airlines flying from The Big Island to Chicago

Discover the top 2 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 July 18, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$422Average$834FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$447Average$597FlexibilityNo cancel feeOn-time69%

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