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$226+ 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 4/21. Fares are subject to change and may not be available on all flights or dates of travel.
OGG — CHI
Apr 25 — May 21
Sat 4/25
Sat 5/2
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 March 26, 2026.

This Alaska Airlines deal was found by Cheapflights users on 3/24. 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 4/2310:51 pm
OGG
-
ORD
1 stop33h 22m
Multiple Airlines
Mon 4/278:50 am
ORD
-
OGG
2 stops16h 35m
Multiple Airlines
Deal found 3/24$491
This Alaska Airlines deal was found by Cheapflights users on 3/25. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/2310:51 pm
OGG
-
ORD
1 stop33h 22m
Alaska Airlines
Mon 4/277:59 pm
ORD
-
OGG
1 stop29h 53m
Alaska Airlines
Deal found 3/25$500
This American Airlines deal was found by Cheapflights users on 3/26. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/83:03 pm
OGG
-
ORD
1 stop11h 15m
American Airlines
Sun 5/106:00 am
ORD
-
OGG
1 stop12h 24m
American Airlines
Deal found 3/26$580
This Delta deal was found by Cheapflights users on 3/25. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/138:00 pm
OGG
-
ORD
2 stops15h 29m
Delta
Wed 5/207:12 am
ORD
-
OGG
1 stop15h 36m
Delta
Deal found 3/25$583
This Delta deal was found by Cheapflights users on 3/26. 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.
Fri 5/88:00 pm
OGG
-
ORD
1 stop10h 52m
Delta
Sun 5/108:42 am
ORD
-
OGG
2 stops15h 53m
Delta
Deal found 3/26$613
This Southwest deal was found by Cheapflights users on 3/24. 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 9/248:25 pm
OGG
-
MDW
1 stop9h 55m
Southwest
Wed 10/710:00 am
MDW
-
OGG
1 stop11h 10m
Southwest
Deal found 3/24$614
This Alaska Airlines deal was found by Cheapflights users on 3/24. 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 9/241:10 pm
OGG
-
ORD
1 stop12h 50m
Multiple Airlines
Wed 10/79:20 am
ORD
-
OGG
1 stop17h 41m
Multiple Airlines
Deal found 3/24$614
This Southwest deal was found by Cheapflights users on 3/23. 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 4/68:55 pm
OGG
-
MDW
1 stop14h 40m
Southwest
Fri 4/106:55 am
MDW
-
OGG
1 stop12h 15m
Southwest
Deal found 3/23$734
This Southwest deal was found by Cheapflights users on 3/23. 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.
Tue 4/78:25 pm
OGG
-
MDW
2 stops12h 45m
Southwest
Sat 4/115:10 am
MDW
-
OGG
2 stops13h 30m
Southwest
Deal found 3/23$745
This Southwest deal was found by Cheapflights users on 3/24. 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.
Sat 9/199:10 am
OGG
-
MDW
1 stop15h 45m
Southwest
Fri 10/96:30 am
MDW
-
OGG
1 stop12h 15m
Southwest
Deal found 3/24$759
This Southwest deal was found by Cheapflights users on 3/26. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/59:10 am
OGG
-
MDW
1 stop15h 45m
Southwest
Sun 9/67:10 am
MDW
-
OGG
1 stop10h 40m
Southwest
Deal found 3/26$799

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 March 26, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$491
(Alaska Airlines)

One-way from

$226
(Kiwi.com)

Good round-trip deal

$738 or less

Good one-way deal

$313 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
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 March 26, 2026.
Use the filters below to find and compare flights from Kahului to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Thu 4/23

10:51 pm-1:13 pm

1 stop33h 22m

Chicago O'Hare Intl

Mon 4/27

8:50 am-8:25 pm

2 stops16h 35m

$491

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Thu 4/23

10:51 pm-1:13 pm

1 stop33h 22m

Chicago O'Hare Intl

Mon 4/27

3:52 pm-8:52 pm

1 stop34h 00m

$500

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Sat 9/5

4:25 pm-1:54 pm

2 stops16h 29m

Chicago O'Hare Intl

Sun 9/6

2:54 pm-10:01 pm

1 stop12h 07m

$644

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Mon 4/6

8:55 pm-4:35 pm

1 stop14h 40m

Chicago Midway

Fri 4/10

6:55 am-2:10 pm

1 stop12h 15m

$734
Quickest round-trip

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Thu 4/9

8:25 pm-12:45 pm

1 stop11h 20m

Chicago Midway

Mon 4/13

6:55 am-2:10 pm

1 stop12h 15m

$734

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Tue 4/7

8:35 pm-2:15 pm

2 stops12h 40m

Chicago Midway

Sat 4/11

5:10 am-12:55 pm

1 stop12h 45m

$740

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Sat 9/19

9:10 am-5:55 am

1 stop15h 45m

Chicago Midway

Fri 10/9

6:30 am-1:45 pm

1 stop12h 15m

$759
Cheapest one-way

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Tue 4/21

9:15 pm-4:39 pm

1 stop14h 24m

$235

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Mon 4/27

9:15 pm-1:23 pm

1 stop11h 08m

$235

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Tue 4/28

12:30 pm-10:19 am

2 stops16h 49m

$241

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/25

Showing 1-10 of 25 resultsSorted by cheapest first
1
2
3

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 March.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*3 stars
ExpediaPrice Accuracy1 starTrust 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 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 March 26, 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 2 different airlines.

  • How long is the flight from Kahului to Chicago?

    Alaska Airlines, Delta, and Southwest can get you from Kahului to Chicago in just under 11h 20m. Your travel time can differ by up to 22h 02m. 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 $461, American Airlines will fly you from Kahului to Chicago and back. In addition to American Airlines, many other airlines offer competitively priced options for your trip. Check Cheapflights for deals on Alaska Airlines for as low as $468.

  • 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 $583, our data indicates the cheapest price to be $279. The most popular route (Kahului - Chicago O'Hare Intl), is priced around $491.

  • 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

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
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Top 2 airlines flying from Kahului to Chicago

Discover the top 2 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 March 26, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$461Average$818FlexibilityNo cancel feeOn-time71%
Alaska AirlinesCheapest$468Average$715FlexibilityNo cancel feeOn-time75%

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