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$195+ 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 5/4. Fares are subject to change and may not be available on all flights or dates of travel.
OGG — CHI
Feb 21 — Feb 281
Sat 2/21
Sat 2/28
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 January 22, 2026.

This Expedia deal was found by Cheapflights users on 1/19. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/3011:02 pm
OGG
-
ORD
1 stop10h 19m
Alaska Airlines
Mon 4/138:20 am
ORD
-
OGG
1 stop18h 42m
Alaska Airlines
Deal found 1/19$497
This Expedia deal was found by Cheapflights users on 1/19. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/3011:02 pm
OGG
-
ORD
1 stop10h 19m
Multiple Airlines
Mon 4/138:20 am
ORD
-
OGG
2 stops17h 05m
Multiple Airlines
Deal found 1/19$516
This Delta deal was found by Cheapflights users on 1/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/114:00 pm
OGG
-
ORD
1 stop11h 30m
Delta
Mon 3/167:10 am
ORD
-
OGG
2 stops16h 15m
Delta
Deal found 1/20$532
This Expedia deal was found by Cheapflights users on 1/21. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/2011:54 pm
OGG
-
ORD
1 stop11h 04m
Alaska Airlines
Fri 2/271:00 pm
ORD
-
OGG
1 stop13h 54m
Alaska Airlines
Deal found 1/21$537
This Delta deal was found by Cheapflights users on 1/21. 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.
Fri 2/201:53 pm
OGG
-
ORD
2 stops16h 32m
Delta
Fri 2/277:15 am
ORD
-
OGG
1 stop16h 00m
Delta
Deal found 1/21$562
This American Airlines deal was found by Cheapflights users on 1/21. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/202:46 pm
OGG
-
ORD
1 stop11h 09m
American Airlines
Fri 2/279:45 am
ORD
-
OGG
1 stop13h 38m
American Airlines
Deal found 1/21$623
This WAYA deal was found by Cheapflights users on 1/20. 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 WAYA is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/202:30 pm
OGG
-
ORD
1 stop10h 58m
Multiple Airlines
Tue 8/116:00 am
ORD
-
OGG
1 stop11h 52m
Multiple Airlines
Deal found 1/20$641
This Kiwi.com deal was found by Cheapflights users on 1/21. 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 3/266:00 am
OGG
-
ORD
2 stops12h 59m
Multiple Airlines
Sun 4/57:59 pm
ORD
-
OGG
1 stop31h 03m
Multiple Airlines
Deal found 1/21$650
This Kiwi.com deal was found by Cheapflights users on 1/19. 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 10/11:10 pm
OGG
-
ORD
1 stop12h 50m
Multiple Airlines
Mon 10/56:00 am
ORD
-
OGG
1 stop12h 15m
Multiple Airlines
Deal found 1/19$653
This Southwest deal was found by Cheapflights users on 1/20. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/2010:00 am
OGG
-
MDW
1 stop15h 00m
Southwest
Tue 8/116:00 am
MDW
-
OGG
1 stop11h 50m
Southwest
Deal found 1/20$664
This Delta deal was found by Cheapflights users on 1/21. 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.
Fri 2/201:53 pm
OGG
-
MDW
2 stops17h 10m
Delta
Fri 2/276:00 am
MDW
-
OGG
1 stop13h 37m
Delta
Deal found 1/21$705
This Southwest deal was found by Cheapflights users on 1/21. 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.
Fri 2/69:35 pm
OGG
-
MDW
1 stop10h 15m
Southwest
Mon 2/98:10 am
MDW
-
OGG
1 stop12h 15m
Southwest
Deal found 1/21$714

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 January 22, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

Expedia
3 stars

Round-trip from

$497
(Expedia)

One-way from

$195
(Kiwi.com)

Popular in

June

Cheapest in

January

Average price

$434

Good round-trip deal

$419 or less

Good one-way deal

$299 or less
Provider with most accurate pricing for Kahului-Chicago (CHI) flight deals.
Search Deals
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. 15% potential increase in price ($116 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($25 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
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 January 22, 2026.
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

Wed 3/11

4:00 pm-8:30 am

1 stop11h 30m

Chicago O'Hare Intl

Mon 3/16

7:10 am-6:25 pm

2 stops16h 15m

$532

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Fri 2/20

11:54 pm-2:58 pm

1 stop11h 04m

Chicago O'Hare Intl

Fri 2/27

1:00 pm-10:54 pm

1 stop13h 54m

$537

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Fri 2/20

1:53 pm-10:25 am

2 stops16h 32m

Chicago O'Hare Intl

Fri 2/27

7:15 am-7:15 pm

1 stop16h 00m

$562

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Fri 2/20

2:46 pm-5:55 am

1 stop11h 09m

Chicago O'Hare Intl

Fri 2/27

9:45 am-7:23 pm

1 stop13h 38m

$623

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Mon 7/20

2:30 pm-6:28 am

1 stop10h 58m

Chicago O'Hare Intl

Tue 8/11

6:00 am-12:52 pm

1 stop11h 52m

$641

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Wed 7/15

7:00 am-11:59 pm

1 stop11h 59m

Chicago O'Hare Intl

Wed 7/22

7:20 am-8:40 pm

1 stop18h 20m

$654

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Thu 3/26

8:00 am-6:39 am

1 stop17h 39m

Chicago O'Hare Intl

Sun 4/5

4:10 pm-10:02 pm

1 stop34h 52m

$660

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Mon 3/30

9:00 pm-3:14 pm

2 stops13h 14m

Chicago O'Hare Intl

Mon 4/13

8:20 am-6:40 pm

2 stops15h 20m

$662

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Mon 7/20

10:00 am-6:00 am

1 stop15h 00m

Chicago Midway

Tue 8/11

6:00 am-12:50 pm

1 stop11h 50m

$664

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Fri 2/20

1:53 pm-11:03 am

2 stops17h 10m

Chicago Midway

Fri 2/27

6:00 am-3:37 pm

1 stop13h 37m

$705

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/21

Showing 1-10 of 33 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 January.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*1 star
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 Expedia the most. Expedia 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 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 January 22, 2026.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Kahului to Chicago as you normally would.

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 is 1 daily outbound flight to Chicago from 3 different airlines.

  • How long is the flight from Kahului to Chicago?

    Delta, Alaska Airlines, and Southwest can get you from Kahului to Chicago in just under 11h 04m. Your travel time can differ by up to 3h 56m. 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 Alaska Airlines - these airlines can fly you to your destination from $455 and $468, respectively. Hawaiian Airlines is priced at 49% lower than the current average price of a flight leaving 3 months from now.

  • 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 $212, 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 $748, our data indicates the cheapest price to be $201. The most popular route (Kahului - Chicago O'Hare Intl), is priced around $462.

  • 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.

See more FAQs

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Top 3 airlines flying from Kahului to Chicago

Discover the top 3 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 January 22, 2026.
AirlineCheapestAverageFlexibilityOn-time
Hawaiian AirlinesCheapest$322Average$715FlexibilityNo cancel feeOn-time85%
American AirlinesCheapest$455Average$733FlexibilityNo cancel feeOn-time71%
Alaska AirlinesCheapest$468Average$683FlexibilityNo cancel feeOn-time75%

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