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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 5/6. Fares are subject to change and may not be available on all flights or dates of travel.
OGG — CHI
Apr 11 — Apr 181
Sat 4/11
Sat 4/18
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 12, 2026.

This Kiwi.com deal was found by Cheapflights users on 3/9. 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.
Wed 4/153:10 pm
OGG
-
ORD
1 stop33h 40m
Multiple Airlines
Mon 4/207:35 am
ORD
-
OGG
2 stops32h 42m
Multiple Airlines
Deal found 3/9$406
This Southwest deal was found by Cheapflights users on 3/10. 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 4/208:55 pm
OGG
-
MDW
1 stop14h 40m
Southwest
Mon 4/2710:05 am
MDW
-
OGG
1 stop11h 00m
Southwest
Deal found 3/10$445
This American Airlines deal was found by Cheapflights users on 3/10. 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.
Mon 4/203:03 pm
OGG
-
ORD
1 stop10h 44m
American Airlines
Mon 4/271:18 pm
ORD
-
OGG
1 stop11h 38m
American Airlines
Deal found 3/10$448
This Southwest deal was found by Cheapflights users on 3/10. 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 4/168:55 pm
OGG
-
MDW
1 stop11h 10m
Southwest
Mon 4/206:40 am
MDW
-
OGG
1 stop10h 55m
Southwest
Deal found 3/10$451
This Kiwi.com deal was found by Cheapflights users on 3/10. 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 4/1611:45 am
OGG
-
ORD
2 stops37h 05m
Multiple Airlines
Mon 4/207:56 pm
ORD
-
OGG
1 stop20h 21m
Multiple Airlines
Deal found 3/10$453
This Alaska Airlines deal was found by Cheapflights users on 3/8. 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 5/710:51 pm
OGG
-
ORD
1 stop19h 52m
Alaska Airlines
Mon 5/117:59 pm
ORD
-
OGG
1 stop29h 53m
Alaska Airlines
Deal found 3/8$454
This Expedia deal was found by Cheapflights users on 3/10. 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 4/2710:51 pm
OGG
-
ORD
1 stop15h 12m
Alaska Airlines
Wed 5/68:50 am
ORD
-
OGG
2 stops18h 30m
Alaska Airlines
Deal found 3/10$458
This American Airlines deal was found by Cheapflights users on 3/10. 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.
Thu 4/169:48 pm
OGG
-
ORD
1 stop10h 19m
American Airlines
Mon 4/205:00 am
ORD
-
OGG
1 stop14h 01m
American Airlines
Deal found 3/10$460
This Delta deal was found by Cheapflights users on 3/10. 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.
Thu 4/1610:30 pm
OGG
-
ORD
2 stops14h 34m
Delta
Tue 4/217:15 am
ORD
-
OGG
1 stop15h 21m
Delta
Deal found 3/10$468
This Delta deal was found by Cheapflights users on 3/10. 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.
Mon 4/279:15 pm
OGG
-
ORD
2 stops17h 37m
Delta
Wed 5/68:50 am
ORD
-
OGG
2 stops15h 42m
Delta
Deal found 3/10$476
This Southwest deal was found by Cheapflights users on 3/10. 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 4/168:55 pm
OGG
-
MDW
1 stop11h 10m
Southwest
Tue 4/217:55 am
MDW
-
OGG
2 stops13h 10m
Southwest
Deal found 3/10$486
This Alaska Airlines deal was found by Cheapflights users on 3/9. 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 4/1611:02 pm
OGG
-
ORD
1 stop19h 57m
Alaska Airlines
Mon 4/204:10 pm
ORD
-
OGG
1 stop34h 52m
Alaska Airlines
Deal found 3/9$492

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 12, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$406
(Kiwi.com)

One-way from

$195
(Alaska Airlines)

Good round-trip deal

$657 or less

Good one-way deal

$302 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 12, 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
Quickest round-trip

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Mon 4/20

8:55 pm-4:35 pm

1 stop14h 40m

Chicago Midway

Mon 4/27

10:05 am-4:05 pm

1 stop11h 00m

$445

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Thu 5/7

10:51 pm-11:43 pm

1 stop19h 52m

Chicago O'Hare Intl

Mon 5/11

7:59 pm-8:52 pm

1 stop29h 53m

$454

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Thu 4/16

11:02 pm-7:02 pm

1 stop15h 00m

Chicago O'Hare Intl

Mon 4/20

4:10 pm-10:02 pm

1 stop34h 52m

$492

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Thu 4/16

11:02 pm-11:59 pm

1 stop19h 57m

Chicago O'Hare Intl

Mon 4/20

7:59 pm-2:07 pm

2 stops23h 08m

$496

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Mon 4/20

10:30 pm-6:04 pm

2 stops14h 34m

Chicago O'Hare Intl

Mon 4/27

7:15 am-5:36 pm

1 stop15h 21m

$499

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Thu 5/7

10:00 pm-4:29 pm

2 stops13h 29m

Chicago O'Hare Intl

Mon 5/11

7:12 am-5:48 pm

1 stop15h 36m

$509

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Thu 4/16

8:25 pm-2:20 pm

2 stops12h 55m

Chicago Midway

Mon 4/20

6:55 am-4:05 pm

2 stops14h 10m

$539

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Thu 4/16

6:00 am-11:55 pm

2 stops12h 55m

Chicago Midway

Tue 4/21

7:55 am-4:05 pm

2 stops13h 10m

$568

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Thu 5/7

8:55 pm-5:55 pm

1 stop16h 00m

Chicago Midway

Mon 5/11

6:55 am-4:05 pm

2 stops14h 10m

$630

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Thu 4/9

8:55 pm-1:05 pm

1 stop11h 10m

Chicago Midway

Sat 4/18

6:55 am-4:35 pm

2 stops14h 40m

$799

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/8

Showing 1-10 of 31 resultsSorted by cheapest first
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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 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 12, 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.

Weekly flight availability from Kahului to Chicago

Explore weekly flight availability from Kahului to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated March 12, 2026.

The most flights from OGG to CHI are scheduled on a Monday (2 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (2 on average).

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 2 daily outbound flights to Chicago from 3 different airlines.

  • How long is the flight from Kahului to Chicago?

    Southwest, Alaska Airlines, and Delta can get you from Kahului to Chicago in just under 14h 34m. Your travel time can differ by up to 5h 18m. 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.

  • 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 $941, our data indicates the cheapest price to be $265. The most popular route (Kahului - Chicago O'Hare Intl), is priced around $493.

  • 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?

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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 March 12, 2026.
AirlineCheapestAverageFlexibilityOn-time
Hawaiian AirlinesCheapest$322Average$629FlexibilityNo cancel feeOn-time85%
American AirlinesCheapest$455Average$733FlexibilityNo cancel feeOn-time71%
Alaska AirlinesCheapest$468Average$683FlexibilityNo cancel feeOn-time75%

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