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$186+ Cheap flights from Kahului (OGG) 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 2/9. Fares are subject to change and may not be available on all flights or dates of travel.
OGG — CHI
Jan 22 — Jan 291
Thu 1/22
Thu 1/29
1 adult, Economy
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Cheap flight deals from Kahului to Chicago

Cheapest flights from Kahului to Chicago
Explore the most affordable flight options available from Kahului to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 23, 2025.

This Alaska Airlines deal was found by Cheapflights users on 12/21. 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 12/3110:37 pmOGG - ORD
1 stop10h 39mAlaska Airlines
Mon 1/58:39 amORD - OGG
1 stop16h 58mAlaska Airlines
Deal found 12/21$758
This Southwest deal was found by Cheapflights users on 12/21. 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 12/319:35 pmOGG - ORD
1 stop13h 50mSouthwest
Mon 1/57:15 amORD - OGG
2 stops13h 20mSouthwest
Deal found 12/21$783
This Alaska Airlines deal was found by Cheapflights users on 12/21. 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 12/317:25 pmOGG - ORD
2 stops15h 12mMultiple Airlines
Mon 1/56:00 amORD - OGG
2 stops15h 40mMultiple Airlines
Deal found 12/21$900
This United Airlines deal was found by Cheapflights users on 12/21. 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 12/315:15 pmOGG - ORD
Nonstop7h 59mUnited Airlines
Mon 1/59:20 amORD - OGG
Nonstop9h 24mUnited Airlines
Deal found 12/21$1,179

Find flight deals from Kahului to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Kahului (OGG) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated December 23, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$383
(Kiwi.com)

One-way from

$186
(Kiwi.com)

Good round-trip deal

$485 or less

Good one-way deal

$242 or less
Provider with most accurate pricing for Kahului-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Kahului-Chicago (CHI) flights.
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From Kahului to Chicago (CHI)
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One-way flight from Kahului to Chicago (CHI)
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Price to beat on a round-trip flight from Kahului to Chicago (CHI).
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Price to beat on a one-way flight from Kahului to Chicago (CHI).
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Cheapflights Fare Finder

 
Customize your flight search to find flights from Kahului 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 December 23, 2025.
Use the filters below to find and compare flights from Kahului to Chicago that are best for you.

Fly from

Kahului

Fly to

Chicago

Route

Depart

Return

Price

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Tue 1/27

11:59 pm-11:37 pm

1 stop19h 38m

Chicago O'Hare Intl

Tue 2/3

3:44 pm-2:27 pm

2 stops26h 43m

$389

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Wed 1/28

6:00 am-11:37 pm

2 stops13h 37m

Chicago O'Hare Intl

Tue 2/3

9:00 am-10:59 pm

1 stop17h 59m

$390

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Wed 1/21

11:59 pm-11:37 pm

1 stop19h 38m

Chicago O'Hare Intl

Wed 1/28

9:00 am-10:59 pm

1 stop17h 59m

$392

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Thu 1/29

11:59 pm-11:37 pm

1 stop19h 38m

Chicago O'Hare Intl

Tue 2/3

9:00 am-10:59 pm

1 stop17h 59m

$394

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Thu 1/29

11:59 pm-2:29 pm

1 stop10h 30m

Chicago O'Hare Intl

Wed 2/4

9:00 am-10:59 pm

1 stop17h 59m

$394

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Wed 1/28

6:00 am-11:37 pm

2 stops13h 37m

Chicago O'Hare Intl

Mon 2/2

9:00 am-10:59 pm

1 stop17h 59m

$399

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Wed 1/28

6:00 am-11:37 pm

2 stops13h 37m

Chicago O'Hare Intl

Thu 2/5

9:00 am-10:59 pm

1 stop17h 59m

$399

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Fri 1/30

11:59 pm-2:29 pm

1 stop10h 30m

Chicago O'Hare Intl

Tue 2/3

9:00 am-10:59 pm

1 stop17h 59m

$403

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Thu 1/29

11:59 pm-11:37 pm

1 stop19h 38m

Chicago O'Hare Intl

Mon 2/2

9:00 am-10:59 pm

1 stop17h 59m

$404

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Thu 1/29

7:06 pm-2:29 pm

2 stops15h 23m

Chicago O'Hare Intl

Wed 2/4

9:00 am-10:21 pm

2 stops17h 21m

$404

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/22

Showing 1-10 of 44 results
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Compare providers for flights from Kahului to Chicago

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Kahului to Chicago in December.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*1 star
ExpediaPrice Accuracy2 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Kahului-Chicago flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Kahului-Chicago flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Kahului-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Kahului-Chicago flights, Cheapflights users trust eDreams the most. eDreams has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Kahului-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Kahului to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Kahului 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 Kahului to Chicago

What is the cheapest month to book a flight from Kahului to Chicago?

Currently, November is the cheapest month in which you can book a flight from Kahului to Chicago (average of $222). Flying from Kahului to Chicago in February is currently the most expensive (average of $812). 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 OGG to CHI?

Find hourly flight availability from Kahului 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 December 23, 2025.

It’s optimal to fly from Kahului to Chicago in the evening. By choosing this option you can save up to 12% on the cost of your flight, compared to a flight in the morning.

Weekly flight availability from Kahului to Chicago

Explore weekly flight availability from Kahului to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated December 23, 2025.

The most flights from OGG to CHI are scheduled on a Monday (2 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (2 on average).

Related info for your journey

Find useful and relevant information for your journey from Kahului to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Kahului to Chicago?

    Located just 2.7 mi from the city center, Kahului is the airport most travelers will use when flying to Chicago from Kahului. Booking flights from Kahului (OGG) to Chicago should be relatively easy as there are 2 daily outbound flights to Chicago from 4 different airlines.

  • How long is the flight from Kahului to Chicago?

    Alaska Airlines and Delta can get you from Kahului to Chicago in just under 12h 43m. Your travel time can differ by up to 6h 55m. Airlines will cover a distance of 4184 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the cheapest airlines flying from Kahului to Chicago round-trip?

    Currently priced at $322, Hawaiian Airlines will fly you from Kahului to Chicago and back. In addition to Hawaiian Airlines, many other airlines offer competitively priced options for your trip. Search Cheapflights for deals from American Airlines and Alaska Airlines - these airlines can fly you to your destination from $455 and $468, respectively.

  • What are the cheapest airlines to fly from Kahului to Chicago one-way?

    $210 is the cheapest one-way deal found within the past few days, from Southwest. You may also be able to find cheap deals on Delta and American Airlines, with prices starting from $211 and $230, respectively.

  • What are the cheapest flights from Kahului to Chicago?

    Looking for the cheapest flight from Kahului to Chicago? While on average our users pay $780, our data indicates the cheapest price to be $221. The most popular route (Kahului - Chicago O'Hare Intl), is priced around $407.

  • Can I find deals for flights from Kahului to Chicago that include hotel bookings?

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

  • How can I find direct flights from Kahului to Chicago?

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

  • Can I find deals for business class flights from Kahului to Chicago?

    Yes. Cheapflights offers flight deals from Kahului 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 Kahului to Chicago?

    Currently, November is the cheapest month in which you can book a flight from Kahului to Chicago (average of $222). Flying from Kahului to Chicago in February is currently the most expensive (average of $812). 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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Top 4 airlines flying from Kahului to Chicago

Discover the top 4 airlines that operate flights from Kahului 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 December 23, 2025.
AirlineCheapestAverageFlexibilityOn-time
Hawaiian AirlinesCheapest$322Average$715FlexibilityNo cancel feeOn-time85%
American AirlinesCheapest$455Average$733FlexibilityNo cancel feeOn-time71%
Alaska AirlinesCheapest$468Average$635FlexibilityNo cancel feeOn-time75%
United AirlinesCheapest$793Average$1,193FlexibilityNo cancel feeOn-time69%

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