HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$183+ 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 3/10. Fares are subject to change and may not be available on all flights or dates of travel.
OGG — CHI
Mar 6 — Mar 131
Fri 3/6
Fri 3/13
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Kahului to Chicago with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 February 4, 2026.

This Alaska Airlines deal was found by Cheapflights users on 2/3. 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.
Tue 3/311:54 pm
OGG
-
ORD
1 stop20h 05m
Alaska Airlines
Tue 3/108:20 am
ORD
-
OGG
1 stop19h 26m
Alaska Airlines
Deal found 2/3$383
This Expedia deal was found by Cheapflights users on 2/3. 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.
Tue 3/311:54 pm
OGG
-
ORD
1 stop20h 05m
Multiple Airlines
Tue 3/108:20 am
ORD
-
OGG
2 stops19h 01m
Multiple Airlines
Deal found 2/3$389
This Delta deal was found by Cheapflights users on 2/3. 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.
Tue 3/31:53 pm
OGG
-
ORD
2 stops15h 48m
Delta
Tue 3/107:10 am
ORD
-
OGG
2 stops16h 15m
Delta
Deal found 2/3$433
This Alaska Airlines deal was found by Cheapflights users on 2/2. 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 3/161:04 pm
OGG
-
ORD
1 stop29h 55m
Alaska Airlines
Tue 3/312:09 pm
ORD
-
OGG
1 stop12h 25m
Alaska Airlines
Deal found 2/2$470
This American Airlines deal was found by Cheapflights users on 2/1. 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 5/139:59 pm
OGG
-
ORD
1 stop11h 17m
American Airlines
Tue 5/263:20 pm
ORD
-
OGG
1 stop10h 57m
American Airlines
Deal found 2/1$481
This Alaska Airlines deal was found by Cheapflights users on 2/1. 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 2/1811:54 pm
OGG
-
ORD
1 stop20h 05m
Alaska Airlines
Sun 2/228:20 am
ORD
-
OGG
1 stop34h 32m
Alaska Airlines
Deal found 2/1$522
This American Airlines deal was found by Cheapflights users on 2/3. 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.
Tue 3/311:46 pm
OGG
-
ORD
1 stop12h 39m
American Airlines
Sun 4/59:45 am
ORD
-
OGG
1 stop13h 38m
American Airlines
Deal found 2/3$551
This CheapOair deal was found by Cheapflights users on 2/1. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/137:00 pm
OGG
-
ORD
2 stops14h 47m
Multiple Airlines
Tue 5/269:00 am
ORD
-
OGG
1 stop17h 30m
Multiple Airlines
Deal found 2/1$586
This Kiwi.com deal was found by Cheapflights users on 2/3. 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
Mon 3/307:59 pm
ORD
-
OGG
1 stop31h 03m
Multiple Airlines
Deal found 2/3$587
This Southwest deal was found by Cheapflights users on 2/2. 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 2/189:35 pm
OGG
-
MDW
1 stop12h 10m
Southwest
Sun 2/225:00 am
MDW
-
OGG
1 stop12h 30m
Southwest
Deal found 2/2$714
This Southwest deal was found by Cheapflights users on 2/2. 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 2/179:35 pm
OGG
-
MDW
1 stop11h 00m
Southwest
Sat 2/216:10 am
MDW
-
OGG
2 stops14h 10m
Southwest
Deal found 2/2$720
This Southwest deal was found by Cheapflights users on 2/2. 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 6/310:00 am
OGG
-
MDW
1 stop15h 00m
Southwest
Thu 6/47:30 am
MDW
-
OGG
2 stops13h 40m
Southwest
Deal found 2/2$765

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 February 4, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$383
(Alaska Airlines)

One-way from

$183
(Kiwi.com)

Popular in

June

Cheapest in

January

Average price

$447

Good round-trip deal

$464 or less

Good one-way deal

$305 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 February 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 February 4, 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

Tue 3/3

11:54 pm-11:59 pm

1 stop20h 05m

Chicago O'Hare Intl

Tue 3/10

8:20 am-10:46 pm

1 stop19h 26m

$383

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Tue 3/3

11:54 pm-11:59 pm

1 stop20h 05m

Chicago O'Hare Intl

Tue 3/10

8:20 am-10:21 pm

2 stops19h 01m

$389

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Tue 3/3

1:53 pm-9:41 am

2 stops15h 48m

Chicago O'Hare Intl

Tue 3/10

7:10 am-6:25 pm

2 stops16h 15m

$433

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Mon 3/16

1:04 pm-11:59 pm

1 stop29h 55m

Chicago O'Hare Intl

Tue 3/31

2:09 pm-9:34 pm

1 stop12h 25m

$470

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Wed 5/13

9:59 pm-2:16 pm

1 stop11h 17m

Chicago O'Hare Intl

Tue 5/26

3:20 pm-9:17 pm

1 stop10h 57m

$481

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Tue 3/31

1:46 pm-7:25 am

1 stop12h 39m

Chicago O'Hare Intl

Sun 4/5

9:45 am-6:23 pm

1 stop13h 38m

$551

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Thu 3/26

6:00 am-11:59 pm

2 stops12h 59m

Chicago O'Hare Intl

Mon 3/30

7:59 pm-10:02 pm

1 stop31h 03m

$587

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Tue 3/31

8:25 pm-1:55 pm

2 stops12h 30m

Chicago O'Hare Intl

Sun 4/5

6:15 am-12:30 pm

1 stop11h 15m

$622

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Wed 2/18

7:48 pm-4:33 pm

2 stops16h 45m

Chicago O'Hare Intl

Sun 2/22

8:20 am-2:52 pm

1 stop34h 32m

$639

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Thu 2/19

11:54 pm-2:58 pm

1 stop11h 04m

Chicago O'Hare Intl

Mon 2/23

8:20 am-11:46 pm

1 stop19h 26m

$642

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/2

Showing 1-10 of 37 results
1
2
3
4

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 February.
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 February 4, 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?

    Alaska Airlines, Delta, and American Airlines can get you from Kahului to Chicago in just under 11h 17m. Your travel time can differ by up to 8h 48m. 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 $973, our data indicates the cheapest price to be $201. The most popular route (Kahului - Chicago O'Hare Intl), is priced around $389.

  • 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
Lansing
Merrillville
Hammond
Porter
Benton Harbor

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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 February 4, 2026.
AirlineCheapestAverageFlexibilityOn-time
Hawaiian AirlinesCheapest$322Average$715FlexibilityNo cancel feeOn-time85%
American AirlinesCheapest$455Average$733FlexibilityNo cancel feeOn-time71%
Alaska AirlinesCheapest$468Average$683FlexibilityNo cancel feeOn-time75%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.