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Kahului

$140+ Cheap flights from Chicago (CHI) to Kahului (OGG)

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 1/13. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — OGG
Jan 3 — Jan 101
Sat 1/3
Sat 1/10
1 adult, Economy
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Find cheap flights from Chicago to Kahului with Cheapflights

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Cheapflights Tip: The best prices from Chicago to Kahului are usually found in October or September, booked 27 days in advance, depart on a Monday or Tuesday and return on a Wednesday

Cheap flight deals from Chicago to Kahului

Cheapest flights from Chicago to Kahului
Explore the most affordable flight options available from Chicago to Kahului. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 4, 2025.

This KAYAK deal was found by Cheapflights users on 12/3. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/152:05 pmORD - OGG
1 stop12h 15mAlaska Airlines
Wed 1/2111:59 pmOGG - ORD
1 stop10h 30mAlaska Airlines
Deal found 12/3$533
This Alaska Airlines deal was found by Cheapflights users on 12/1. 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.
Tue 12/168:55 amORD - OGG
1 stop18h 45mAlaska Airlines
Wed 12/2411:59 pmOGG - ORD
1 stop16h 03mAlaska Airlines
Deal found 12/1$537
This Alaska Airlines deal was found by Cheapflights users on 12/1. 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.
Tue 12/168:55 amORD - OGG
1 stop18h 45mAlaska Airlines
Mon 12/2211:59 pmOGG - ORD
1 stop20h 00mAlaska Airlines
Deal found 12/1$539
This Kiwi.com deal was found by Cheapflights users on 12/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/156:50 amORD - OGG
2 stops35h 39mMultiple Airlines
Thu 12/254:07 pmOGG - ORD
1 stop33h 58mMultiple Airlines
Deal found 12/1$540
This Alaska Airlines deal was found by Cheapflights users on 12/1. 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.
Mon 12/152:05 pmORD - OGG
1 stop12h 15mAlaska Airlines
Wed 12/2411:59 pmOGG - ORD
1 stop10h 38mAlaska Airlines
Deal found 12/1$547
This Alaska Airlines deal was found by Cheapflights users on 12/1. 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.
Tue 12/163:05 pmORD - OGG
1 stop12h 35mAlaska Airlines
Thu 12/2511:59 pmOGG - ORD
1 stop20h 00mAlaska Airlines
Deal found 12/1$548
This Alaska Airlines deal was found by Cheapflights users on 12/1. 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.
Mon 12/152:05 pmORD - OGG
1 stop12h 15mAlaska Airlines
Mon 12/2211:59 pmOGG - ORD
1 stop20h 00mAlaska Airlines
Deal found 12/1$549
This Alaska Airlines deal was found by Cheapflights users on 12/1. 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.
Tue 12/168:00 amORD - OGG
2 stops18h 20mAlaska Airlines
Tue 12/2311:59 pmOGG - ORD
1 stop16h 03mAlaska Airlines
Deal found 12/1$557
This Alaska Airlines deal was found by Cheapflights users on 12/1. 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.
Mon 12/152:05 pmORD - OGG
1 stop12h 15mAlaska Airlines
Thu 12/2511:59 pmOGG - ORD
1 stop16h 03mAlaska Airlines
Deal found 12/1$558
This Kiwi.com deal was found by Cheapflights users on 12/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/141:52 pmORD - OGG
2 stops26h 27mMultiple Airlines
Thu 12/254:07 pmOGG - ORD
1 stop33h 58mMultiple Airlines
Deal found 12/1$563
This Southwest deal was found by Cheapflights users on 12/3. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/155:15 amMDW - OGG
2 stops14h 50mSouthwest
Wed 1/219:25 pmOGG - MDW
1 stop11h 45mSouthwest
Deal found 12/3$594
This Southwest deal was found by Cheapflights users on 12/3. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/235:10 amMDW - OGG
2 stops13h 40mSouthwest
Tue 1/209:35 pmOGG - MDW
1 stop15h 00mSouthwest
Deal found 12/3$617

Find flight deals from Chicago to Kahului

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Kahului (OGG). 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 December 4, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$423
(Delta)

One-way from

$140
(Alaska Airlines)

Popular in

December

Cheapest in

October

Average price

$953

Good round-trip deal

$906 or less

Good one-way deal

$457 or less
Provider with most accurate pricing for Chicago (CHI)-Kahului flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Kahului flights.
Search Deals
From Chicago (CHI) to Kahului
Search Deals
One-way flight from Chicago (CHI) to Kahului
Search Deals
Highest demand for flights based on searches. 1% potential increase in price ($10 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($19 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals
Price to beat on a round-trip flight from Chicago (CHI) to Kahului.
Search Deals
Price to beat on a one-way flight from Chicago (CHI) to Kahului.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Kahului 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 December 4, 2025.
Use the filters below to find and compare flights from Chicago to Kahului that are best for you.

Fly from

Chicago

Fly to

Kahului

Route

Depart

Return

Price

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Mon 1/19

6:00 am-3:37 pm

1 stop13h 37m

Kahului

Thu 1/29

2:02 pm-9:08 am

2 stops15h 06m

$426

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Wed 1/21

1:49 pm-12:28 pm

2 stops26h 39m

Kahului

Thu 1/29

5:10 pm-9:53 am

1 stop12h 43m

$427

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Sun 1/11

6:45 am-3:37 pm

1 stop12h 52m

Kahului

Mon 1/19

2:02 pm-8:52 am

2 stops14h 50m

$428

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Thu 1/15

6:45 am-3:37 pm

1 stop12h 52m

Kahului

Thu 1/22

2:02 pm-8:52 am

2 stops14h 50m

$428

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Tue 1/20

1:49 pm-12:28 pm

2 stops26h 39m

Kahului

Mon 1/26

5:10 pm-9:53 am

1 stop12h 43m

$429

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Thu 1/22

6:00 am-3:37 pm

1 stop13h 37m

Kahului

Mon 1/26

2:02 pm-9:08 am

2 stops15h 06m

$430

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Mon 1/19

6:00 am-7:15 pm

2 stops17h 15m

Kahului

Wed 1/28

9:05 pm-5:55 pm

2 stops16h 50m

$432

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Tue 1/20

1:49 pm-12:28 pm

2 stops26h 39m

Kahului

Thu 1/29

2:02 pm-9:08 am

2 stops15h 06m

$433

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Sun 1/25

8:35 pm-1:10 pm

2 stops20h 35m

Kahului

Sun 2/1

9:25 pm-1:10 pm

1 stop11h 45m

$434

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Fri 2/20

5:00 am-4:25 pm

2 stops15h 25m

Kahului

Thu 2/26

7:00 pm-12:15 pm

2 stops13h 15m

$441

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/3

Showing 1-10 of 44 results
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Compare providers for flights from Chicago to Kahului

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 Chicago to Kahului in December.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars
CheapfaremartPrice Accuracy-Trust Score*1 star

*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 Chicago-Kahului flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Chicago-Kahului flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Chicago-Kahului flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago-Kahului flights, Cheapflights users trust eDreams the most. eDreams 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 Chicago-Kahului 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 Chicago to Kahului

Have a flexible travel schedule? Discover the best time to fly to Kahului from Chicago 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 Chicago to Kahului

How far ahead should I book a flight from Chicago to Kahului?

Use this chart to determine the optimal time to book a round-trip flight from Chicago to Kahului. Price data was last updated on November 28, 2025.

To ensure you get the cheapest price possible for a flight from Chicago to Kahului, you should look to book at least 27 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

What is the cheapest month to book a flight from Chicago to Kahului?

Currently, January is the cheapest month in which you can book a flight from Chicago to Kahului (average of $380). Flying from Chicago to Kahului in July is currently the most expensive (average of $633). 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 CHI to OGG?

Find hourly flight availability from Chicago to Kahului. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated December 4, 2025.

One of the essential ways to save on airfare from Chicago to Kahului is to remain as flexible as possible. Flights that are in the morning tend to be the most expensive. A flight in the afternoon could potentially save you up to 42% on airfare.

What is the cheapest day to fly from Chicago to Kahului?

Use this chart to determine the cheapest time to fly round-trip from Chicago to Kahului. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Chicago to Kahului flight should consider departing on Tuesday afternoons when fares are most often at their lowest. Monday evenings flights should be avoided if possible as fares are typically the most expensive at this time.

How much does it cost to fly round-trip from Chicago to Kahului?

What’s the top layover airport for flights from Chicago to Kahului?

Share of 1-stop round-trip flights from Chicago to Kahului chosen by Cheapflights users in the past 12 months, using the same layover each way.

San Diego (SAN) – chosen by Cheapflights users on 67% of 1-stop itineraries from Chicago to Kahului on Cheapflights.

What’s the cheapest layover airport for flights from Chicago to Kahului?

Average round-trip fare for 1-stop flights from Chicago to Kahului, chosen by Cheapflights users in the past 12 months, with the same layover each way.

Seattle (SEA) is the most affordable 1-stop option, with an average round-trip price of $514.

What’s the fastest layover option from Chicago to Kahului?

Shortest average travel time for 1-stop one-way flights from Chicago to Kahului, based on itineraries clicked by Cheapflights users over the past 12 months, grouped by layover airport.

Flights via Seattle (SEA) have the shortest average one-way travel time for 1-stop routes: 12h 45m.

Which airport typically offers the quickest layover for flights from Chicago to Kahului?

Average layover duration for 1-stop one-way flights from Chicago to Kahului, chosen by Cheapflights users in the last 12 months, grouped by stopover airport.

Flights via Seattle (SEA) offer the fastest connection on this route, with an average layover time of 2h 05m.

Reviews of airlines servicing Kahului

Get insights into the airlines that provide service to Kahului. 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 Kahului. Reviews last updated December 4, 2025.
Read through reviews of airlines operating flights from Chicago to Kahului, such as Alaska Airlines, Southwest, and Hawaiian Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
11,400 reviews

Comfort

7.8

Overall

8.0

Boarding

8.1

Crew

8.5

Food

7.1

Entertainment

7.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Nov 2025

PDX - BNA

My family especially liked the leg room and comfortable seats.
Alaska Airlines
8.0
Very good
11,400 reviews
Alaska Airlines
8.0
Very good
11,400 reviews

Comfort

7.8

Overall

8.0

Boarding

8.1

Crew

8.5

Food

7.1

Entertainment

7.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Nov 2025

PDX - BNA

My family especially liked the leg room and comfortable seats.
Southwest
8.0
Very good
4,252 reviews
Alaska Airlines
8.0
Very good
11,400 reviews

Comfort

7.8

Overall

8.0

Boarding

8.1

Crew

8.5

Food

7.1

Entertainment

7.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Nov 2025

PDX - BNA

My family especially liked the leg room and comfortable seats.
Hawaiian Airlines
7.8
Good
2,815 reviews
Alaska Airlines
8.0
Very good
11,400 reviews

Comfort

7.8

Overall

8.0

Boarding

8.1

Crew

8.5

Food

7.1

Entertainment

7.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Nov 2025

PDX - BNA

My family especially liked the leg room and comfortable seats.
United Airlines
7.4
Good
9,066 reviews
Alaska Airlines
8.0
Very good
11,400 reviews

Comfort

7.8

Overall

8.0

Boarding

8.1

Crew

8.5

Food

7.1

Entertainment

7.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Nov 2025

PDX - BNA

My family especially liked the leg room and comfortable seats.
American Airlines
7.2
Good
11,044 reviews
Alaska Airlines
8.0
Very good
11,400 reviews

Comfort

7.8

Overall

8.0

Boarding

8.1

Crew

8.5

Food

7.1

Entertainment

7.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Nov 2025

PDX - BNA

My family especially liked the leg room and comfortable seats.

Related info for your journey

Find useful and relevant information for your journey from Chicago to Kahului. 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 into for flights to Kahului from Chicago?

    Located just 2.7 mi from the city center, Kahului is the airport most travelers will use when flying to Kahului from Chicago. Booking flights from Chicago to Kahului (OGG) should be relatively easy as there are 0 daily inbound flights from Chicago from 6 different airlines.

  • How long is the flight from Chicago to Kahului?

    Delta and Alaska Airlines can get you from Chicago to Kahului in just under 13h 37m. Your travel time can differ by up to 11h 40m. Chicago and Kahului are separated by a distance of 4184 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the cheapest airlines flying from Chicago to Kahului round-trip?

    Currently priced at $298, Delta will fly you from Chicago to Kahului and back. In addition to Delta, many other airlines offer competitively priced options for your trip. Search Cheapflights for deals from Hawaiian Airlines and Alaska Airlines - these airlines can fly you to your destination from $307 and $401, respectively. These flights start at 60% lower than the current average price 3 months from now.

  • What are the cheapest airlines to fly from Chicago to Kahului one-way?

    For one-way options, check prices for Delta. According to our data, you can fly for as low as $202. Users have also found prices from $202 and $230 on Hawaiian Airlines and American Airlines, respectively.

  • What are the cheapest flights from Chicago to Kahului?

    While on average a flight from Chicago to Kahului is generally $868, our data shows the cheapest flight currently is $432. When looking at the most popular route, (Chicago O'Hare Intl - Kahului), you can expect to pay $282 for that flight.

  • Where are the most common layover locations when flying from Chicago to Kahului?

    The most popular layover on flights from Chicago to Kahului is Seattle. Phoenix follows Seattle in terms of the most common layover location on Chicago to Kahului flights.

  • What are some popular things to do or see while on a layover in Seattle?

    The majority of Seattle visitors spend their time at Pike Place Market, Space Needle, and Seattle Waterfront. Pike Place Market, Space Needle, and Seattle Waterfront are located about 11.2 mi, 12.0 mi, and 10.9 mi, respectively from Seattle/Tacoma Intl. Those landing in Seattle looking to spend some time exploring during their layover can rent a car for about $48 per day.

  • What are some popular points of interest to see during a layover in Phoenix?

    The majority of Phoenix visitors spend their time at Chase Field, Desert Ridge Marketplace, and Phoenix Symphony Hall. Travelers on a layover in Phoenix can visit Chase Field, Desert Ridge Marketplace, and Phoenix Symphony Hall, by traveling 4.0 mi, 16.7 mi, and 4.3 mi, respectively after landing at Phoenix Sky Harbor Intl. Those landing in Phoenix looking to spend some time exploring during their layover can rent a car for about $51 per day.

  • Where are the least popular layover locations for Chicago to Kahului flights?

    The least popular layover on flights from Chicago to Kahului is Los Angeles.

  • Can I find deals for flights from Chicago to Kahului that include hotel bookings?

    Yes. In addition to deals on Chicago to Kahului flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Kahului?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Kahului.

  • Can I find deals for business class flights from Chicago to Kahului?

    Yes. Cheapflights offers flight deals from Chicago to Kahului 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 Chicago to Kahului?

    Currently, January is the cheapest month in which you can book a flight from Chicago to Kahului (average of $380). Flying from Chicago to Kahului in July is currently the most expensive (average of $633). 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 Kahului?

Book flights to Kahului if you plan to visit one of these locations
Wailea

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Alternative routes for Chicago to Kahului

See prices for flight routes from nearby airports that may be better suited for you.
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Top 6 airlines flying from Chicago to Kahului

Discover the top 6 airlines that operate flights from Chicago to Kahului. 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 December 4, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$355Average$575FlexibilityNo cancel feeOn-timeN/A
Hawaiian AirlinesCheapest$357Average$680FlexibilityNo cancel feeOn-time85%
Alaska AirlinesCheapest$398Average$652FlexibilityNo cancel feeOn-time75%
American AirlinesCheapest$426Average$754FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$568Average$763FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$714Average$1,070FlexibilityNo cancel feeOn-time69%

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