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$173+ 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 1/14. Fares are subject to change and may not be available on all flights or dates of travel.
OGG — CHI
Nov 22 — Nov 291
Sat 11/22
Sat 11/29
1 adult, Economy
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Find 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 October 23, 2025.

This Alaska Airlines deal was found by Cheapflights users on 10/22. 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.
Mon 12/2211:59 pmOGG - ORD
1 stop20h 00mAlaska Airlines
Sun 1/48:39 amORD - OGG
1 stop16h 58mAlaska Airlines
Deal found 10/22$380
This Kiwi.com deal was found by Cheapflights users on 10/20. 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.
Wed 12/109:51 amOGG - ORD
2 stops40h 09mMultiple Airlines
Sat 12/139:06 pmORD - OGG
1 stop19h 13mMultiple Airlines
Deal found 10/20$470
This American Airlines deal was found by Cheapflights users on 10/20. 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 12/107:00 pmOGG - ORD
1 stop11h 34mAmerican Airlines
Sat 12/136:00 amORD - OGG
1 stop11h 17mAmerican Airlines
Deal found 10/20$473
This Kiwi.com deal was found by Cheapflights users on 10/22. 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.
Fri 11/73:52 pmOGG - ORD
1 stop11h 36mMultiple Airlines
Tue 11/119:22 pmORD - OGG
2 stops20h 40mMultiple Airlines
Deal found 10/22$488
This Alaska Airlines deal was found by Cheapflights users on 10/20. 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 12/106:00 amOGG - ORD
2 stops13h 50mAlaska Airlines
Sat 12/138:55 amORD - OGG
2 stops17h 25mAlaska Airlines
Deal found 10/20$494
This Kiwi.com deal was found by Cheapflights users on 10/22. 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.
Mon 12/2211:59 pmOGG - ORD
1 stop20h 00mAlaska Airlines
Mon 12/298:58 pmORD - OGG
1 stop28h 39mAlaska Airlines
Deal found 10/22$511
This Kiwi.com deal was found by Cheapflights users on 10/21. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/67:25 pmOGG - ORD
2 stops32h 03mMultiple Airlines
Mon 11/109:22 pmORD - OGG
1 stop20h 18mMultiple Airlines
Deal found 10/21$532
This Southwest deal was found by Cheapflights users on 10/22. 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.
Mon 12/229:35 pmOGG - MDW
1 stop10h 40mSouthwest
Mon 12/2910:30 pmMDW - OGG
1 stop17h 55mSouthwest
Deal found 10/22$757
This Delta deal was found by Cheapflights users on 10/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/65:10 pmOGG - MDW
1 stop12h 35mDelta
Mon 11/106:00 amMDW - OGG
1 stop13h 28mDelta
Deal found 10/21$861
This Delta deal was found by Cheapflights users on 10/22. 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 10/309:09 pmOGG - MDW
2 stops20h 05mDelta
Sun 11/25:00 amMDW - OGG
2 stops18h 25mDelta
Deal found 10/22$1,157

Cheap 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 October 23, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$380
(Alaska Airlines)

One-way from

$173
(Alaska Airlines)

Popular in

June

Cheapest in

January

Good round-trip deal

$350 or less

Good one-way deal

$359 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.
Search Deals
From Kahului to Chicago (CHI)
Search Deals
One-way flight from Kahului to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 23% potential increase in price ($212 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 9% potential price decrease ($60 potential savings vs. average RT price).
Search Deals
Price to beat on a round-trip flight from Kahului to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Kahului to Chicago (CHI).
Search Deals

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 October 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

Mon 12/22

11:59 pm-11:59 pm

1 stop20h 00m

Chicago O'Hare Intl

Sun 1/4

8:39 am-9:37 pm

1 stop16h 58m

$380

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Wed 12/10

9:51 am-6:00 am

2 stops40h 09m

Chicago O'Hare Intl

Sat 12/13

9:06 pm-12:19 pm

1 stop19h 13m

$470

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Wed 12/10

7:00 pm-10:34 am

1 stop11h 34m

Chicago O'Hare Intl

Sat 12/13

6:00 am-1:17 pm

1 stop11h 17m

$473

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Fri 11/7

3:52 pm-7:28 am

1 stop11h 36m

Chicago O'Hare Intl

Tue 11/11

9:22 pm-2:02 pm

2 stops20h 40m

$488

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Wed 12/10

6:00 am-11:50 pm

2 stops13h 50m

Chicago O'Hare Intl

Sat 12/13

8:55 am-10:20 pm

2 stops17h 25m

$494

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Mon 12/22

11:59 pm-11:59 pm

1 stop20h 00m

Chicago O'Hare Intl

Mon 12/29

8:58 pm-9:37 pm

1 stop28h 39m

$511

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Thu 3/5

5:00 pm-9:56 am

1 stop12h 56m

Chicago Midway

Sun 3/8

10:35 am-6:40 pm

1 stop13h 05m

$522

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Thu 11/6

7:25 pm-7:28 am

2 stops32h 03m

Chicago O'Hare Intl

Mon 11/10

9:22 pm-1:40 pm

1 stop20h 18m

$532

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Tue 11/4

3:52 pm-7:28 am

1 stop11h 36m

Chicago O'Hare Intl

Mon 11/10

9:22 pm-1:40 pm

1 stop20h 18m

$581

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Thu 3/5

6:30 pm-12:30 pm

2 stops14h 00m

Chicago Midway

Sun 3/8

5:00 am-2:45 pm

2 stops14h 45m

$711

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/21

Showing 1-10 of 27 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 October.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
ExpediaPrice Accuracy2 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 FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Kahului-Chicago flight deals on Cheapflights vs. FlightHub >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 FlightHub the most. FlightHub 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 $220). Flying from Kahului to Chicago in February is currently the most expensive (average of $815). 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 October 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 afternoon.

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 0 daily outbound flights to Chicago from 4 different airlines.

  • How long is the flight from Kahului to Chicago?

    Alaska Airlines, American Airlines, and Delta can get you from Kahului to Chicago in just under 11h 34m. Your travel time can differ by up to 8h 26m. Airlines will cover a distance of 4175 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 United Airlines - these airlines can fly you to your destination from $429 and $432, respectively. Hawaiian Airlines is priced at 52% lower than the current average price of a flight leaving 3 months from now.

  • What are the cheapest flights from Kahului to Chicago?

    Looking for the cheapest flight from Kahului to Chicago? While on average our users pay $586, our data indicates the cheapest price to be $251. The most popular route (Kahului - Chicago O'Hare Intl), is priced around $448.

  • 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 $220). Flying from Kahului to Chicago in February is currently the most expensive (average of $815). 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 October 23, 2025.
AirlineCheapestAverageFlexibilityOn-time
Hawaiian AirlinesCheapest$322Average$715FlexibilityNo cancel feeOn-time85%
American AirlinesCheapest$429Average$729FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$432Average$902FlexibilityNo cancel feeOn-time69%
Alaska AirlinesCheapest$468Average$635FlexibilityNo cancel feeOn-time75%

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