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$190+ 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 12/15. Fares are subject to change and may not be available on all flights or dates of travel.
OGG — CHI
Oct 16 — Oct 231
Thu 10/16
Thu 10/23
1 adult, Economy
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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 September 16, 2025.

Round-trip from

$423
(Alaska Airlines)

One-way from

$190
(Hawaiian Airlines)

Popular in

June

Cheapest in

January

Average price

$466

Good round-trip deal

$280 or less

Good one-way deal

$346 or less
From Kahului to Chicago (CHI)
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One-way flight from Kahului to Chicago (CHI)
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Highest demand for flights based on searches. 26% potential increase in price ($233 potential increase over avg. RT price).
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Cheapest flight prices on average. 9% potential price decrease ($56 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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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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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 September 16, 2025.

This Alaska Airlines deal was found by Cheapflights users on 9/14. 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 11/511:59 pmOGG - ORD
1 stop15h 56mAlaska Airlines
Sun 11/98:59 pmORD - OGG
1 stop29h 51mAlaska Airlines
Deal found 9/14$423
This American Airlines deal was found by Cheapflights users on 9/15. 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 11/267:00 pmOGG - ORD
1 stop11h 36mAmerican Airlines
Sun 11/305:18 amORD - OGG
1 stop11h 59mAmerican Airlines
Deal found 9/15$479
This Alaska Airlines deal was found by Cheapflights users on 9/15. 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.
Fri 11/214:40 pmOGG - ORD
1 stop26h 52mAlaska Airlines
Fri 11/288:49 pmORD - OGG
1 stop28h 41mAlaska Airlines
Deal found 9/15$483
This Delta deal was found by Cheapflights users on 9/14. 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 11/51:35 pmOGG - ORD
2 stops14h 15mDelta
Sun 11/95:32 amORD - OGG
2 stops17h 49mDelta
Deal found 9/14$582
This Alaska Airlines deal was found by Cheapflights users on 9/14. 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.
Sat 11/2211:50 pmOGG - ORD
1 stop19h 42mAlaska Airlines
Sat 11/298:20 amORD - OGG
1 stop17h 10mAlaska Airlines
Deal found 9/14$605
This Kiwi.com deal was found by Cheapflights users on 9/15. 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.
Tue 9/302:55 pmOGG - ORD
1 stop22h 19mMultiple Airlines
Sat 10/48:56 pmORD - OGG
2 stops41h 53mMultiple Airlines
Deal found 9/15$638
This KAYAK deal was found by Cheapflights users on 9/14. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/1911:59 pmOGG - ORD
1 stop16h 04mAlaska Airlines
Wed 12/318:39 amORD - OGG
1 stop17h 00mAlaska Airlines
Deal found 9/14$647
This Kiwi.com deal was found by Cheapflights users on 9/14. 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.
Sat 11/2211:50 pmOGG - ORD
1 stop19h 42mMultiple Airlines
Sat 11/296:02 pmORD - OGG
2 stops32h 25mMultiple Airlines
Deal found 9/14$652
This Alaska Airlines deal was found by Cheapflights users on 9/15. 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 11/2610:30 pmOGG - ORD
2 stops14h 36mAlaska Airlines
Sun 11/308:49 pmORD - OGG
1 stop28h 41mAlaska Airlines
Deal found 9/15$674
This Southwest deal was found by Cheapflights users on 9/14. 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 9/158:30 pmOGG - MDW
1 stop10h 45mSouthwest
Mon 9/225:15 amMDW - OGG
1 stop12h 10mSouthwest
Deal found 9/14$759
This Southwest deal was found by Cheapflights users on 9/14. 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 9/188:25 pmOGG - MDW
1 stop10h 20mSouthwest
Thu 9/255:35 amMDW - OGG
1 stop12h 25mSouthwest
Deal found 9/14$769
This Southwest deal was found by Cheapflights users on 9/14. 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 12/199:35 pmOGG - MDW
1 stop12h 05mSouthwest
Wed 12/315:25 amMDW - OGG
1 stop11h 40mSouthwest
Deal found 9/14$813

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 September 16, 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

Wed 11/5

11:59 pm-7:55 pm

1 stop15h 56m

Chicago O'Hare Intl

Sun 11/9

8:59 pm-10:50 pm

1 stop29h 51m

$423

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Tue 3/3

2:10 pm-5:04 am

1 stop10h 54m

Chicago O'Hare Intl

Wed 3/4

9:00 am-10:48 pm

1 stop17h 48m

$436

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Wed 2/11

6:00 am-11:10 pm

2 stops13h 10m

Chicago O'Hare Intl

Mon 2/16

9:00 am-10:48 pm

1 stop17h 48m

$447

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Sat 1/31

11:20 pm-1:59 pm

1 stop10h 39m

Chicago O'Hare Intl

Sat 2/7

9:00 am-10:48 pm

1 stop17h 48m

$475

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Fri 12/19

9:35 pm-1:40 pm

1 stop12h 05m

Chicago Midway

Wed 12/31

5:25 am-1:05 pm

1 stop11h 40m

$813

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Fri 12/19

9:35 pm-1:40 pm

1 stop12h 05m

Chicago Midway

Tue 12/30

5:00 am-12:25 pm

1 stop11h 25m

$848

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Wed 11/26

8:59 pm-4:39 pm

2 stops15h 40m

Chicago Midway

Sun 11/30

6:00 am-3:28 pm

1 stop13h 28m

$1,078

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Tue 9/30

12:15 pm-8:40 am

2 stops15h 25m

Chicago Midway

Sat 10/4

6:00 am-6:42 pm

2 stops17h 42m

$1,245

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Sat 10/11

11:55 am-8:55 am

2 stops16h 00m

Chicago Midway

Sat 10/18

9:20 am-6:18 pm

2 stops13h 58m

$1,280

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Tue 12/16

11:53 pm-11:50 pm

1 stop19h 57m

$190

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/15

Showing 1-10 of 23 results
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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, August is the cheapest month in which you can book a flight from Kahului to Chicago (average of $245). Flying from Kahului to Chicago in March is currently the most expensive (average of $321). 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 September 16, 2025.

It’s optimal to fly from Kahului to Chicago in the evening. By choosing this option you can save up to 22% on the cost of your flight, compared to a flight in the afternoon.

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated September 16, 2025.
Read through reviews of airlines operating flights from Kahului to Chicago, such as United Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
8,924 reviews

Entertainment

7.1

Crew

8.1

Boarding

7.7

Food

6.6

Comfort

7.3

Overall

7.4

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!
United Airlines
7.4
Good
8,924 reviews
United Airlines
7.4
Good
8,924 reviews

Entertainment

7.1

Crew

8.1

Boarding

7.7

Food

6.6

Comfort

7.3

Overall

7.4

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!

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 and Southwest can get you from Kahului to Chicago in just under 12h 05m. Your travel time can differ by up to 3h 51m. 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 United Airlines - these airlines can fly you to your destination from $399 and $432, respectively. Hawaiian Airlines is priced at 51% 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?

    $190 is the cheapest one-way deal found within the past few days, from Alaska Airlines. You may also be able to find cheap deals on Hawaiian Airlines and Southwest, with prices starting from $212 and $240, 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 $255. The most popular route (Kahului - Chicago O'Hare Intl), is priced around $441.

  • 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, August is the cheapest month in which you can book a flight from Kahului to Chicago (average of $245). Flying from Kahului to Chicago in March is currently the most expensive (average of $321). 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

Traveling to a place near Chicago?

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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 September 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
Hawaiian AirlinesCheapest$322Average$715FlexibilityNo cancel feeOn-time85%
American AirlinesCheapest$399Average$709FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$432Average$863FlexibilityNo cancel feeOn-time69%
Alaska AirlinesCheapest$468Average$635FlexibilityNo cancel feeOn-time75%

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