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$158+ 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
Mar 29 — Apr 51
Sun 3/29
Sun 4/5
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 February 27, 2026.

This deal was found by Cheapflights users on 2/25. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/122:37 pm
OGG
-
ORD
1 stop10h 43m
Alaska Airlines
Tue 5/192:10 pm
ORD
-
OGG
1 stop12h 20m
Alaska Airlines
Deal found 2/25$414
This Southwest deal was found by Cheapflights users on 2/24. 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.
Tue 3/248:25 pm
OGG
-
ORD
1 stop12h 55m
Southwest
Tue 3/316:15 am
ORD
-
OGG
1 stop11h 15m
Southwest
Deal found 2/24$464
This Delta deal was found by Cheapflights users on 2/24. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/244:00 pm
OGG
-
MDW
2 stops15h 29m
Delta
Tue 3/316:00 am
MDW
-
OGG
1 stop14h 13m
Delta
Deal found 2/24$471
This Delta deal was found by Cheapflights users on 2/24. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/189:09 pm
OGG
-
ORD
1 stop11h 16m
Delta
Wed 3/259:50 am
ORD
-
OGG
1 stop13h 35m
Delta
Deal found 2/24$496
This Alaska Airlines deal was found by Cheapflights users on 2/25. 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.
Fri 5/1510:30 pm
OGG
-
ORD
1 stop15h 20m
Alaska Airlines
Wed 5/209:00 am
ORD
-
OGG
2 stops16h 45m
Alaska Airlines
Deal found 2/25$519
This American Airlines deal was found by Cheapflights users on 2/26. 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.
Mon 5/113:03 pm
OGG
-
ORD
1 stop10h 44m
American Airlines
Thu 5/141:18 pm
ORD
-
OGG
1 stop11h 38m
American Airlines
Deal found 2/26$531
This Expedia deal was found by Cheapflights users on 2/26. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/1110:40 am
OGG
-
ORD
2 stops15h 00m
Multiple Airlines
Thu 5/149:00 am
ORD
-
OGG
1 stop17h 30m
Multiple Airlines
Deal found 2/26$534
This Alaska Airlines deal was found by Cheapflights users on 2/26. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/119:52 pm
OGG
-
ORD
2 stops16h 11m
Alaska Airlines
Thu 5/149:00 am
ORD
-
OGG
2 stops16h 45m
Alaska Airlines
Deal found 2/26$538
This Southwest deal was found by Cheapflights users on 2/26. 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.
Mon 5/118:25 pm
OGG
-
MDW
1 stop12h 35m
Southwest
Thu 5/145:10 am
MDW
-
OGG
1 stop13h 00m
Southwest
Deal found 2/26$551
This deal was found by Cheapflights users on 2/25. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/158:00 am
OGG
-
ORD
1 stop10h 59m
Alaska Airlines
Tue 5/192:10 pm
ORD
-
OGG
1 stop12h 20m
Alaska Airlines
Deal found 2/25$557
This Alaska Airlines deal was found by Cheapflights users on 2/25. 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.
Fri 5/154:45 pm
OGG
-
ORD
2 stops15h 37m
Multiple Airlines
Wed 5/209:00 am
ORD
-
OGG
2 stops16h 45m
Multiple Airlines
Deal found 2/25$561
This Southwest deal was found by Cheapflights users on 2/24. 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.
Wed 3/188:25 pm
OGG
-
MDW
1 stop9h 45m
Southwest
Wed 3/255:55 am
MDW
-
OGG
2 stops13h 55m
Southwest
Deal found 2/24$567

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 27, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$414

One-way from

$158
(Kiwi.com)

Good round-trip deal

$597 or less

Good one-way deal

$342 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 February 27, 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

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Fri 5/15

10:30 pm-6:50 pm

1 stop15h 20m

Chicago O'Hare Intl

Wed 5/20

9:00 am-8:45 pm

2 stops16h 45m

$519

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Mon 5/11

3:03 pm-6:47 am

1 stop10h 44m

Chicago O'Hare Intl

Thu 5/14

1:18 pm-7:56 pm

1 stop11h 38m

$531

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Mon 5/11

8:25 pm-2:00 pm

1 stop12h 35m

Chicago Midway

Thu 5/14

5:10 am-1:10 pm

1 stop13h 00m

$551

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Fri 5/15

10:00 pm-5:56 pm

2 stops14h 56m

Chicago Midway

Wed 5/20

9:23 am-7:35 pm

2 stops15h 12m

$564

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Tue 3/24

8:35 pm-1:45 pm

2 stops12h 10m

Chicago Midway

Tue 3/31

5:55 am-2:15 pm

2 stops13h 20m

$582

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Thu 3/19

11:02 pm-11:59 pm

1 stop19h 57m

Chicago O'Hare Intl

Tue 3/24

8:20 am-10:02 pm

1 stop18h 42m

$594

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Wed 3/11

8:25 pm-1:15 pm

1 stop11h 50m

Chicago O'Hare Intl

Mon 3/16

7:00 am-2:15 pm

1 stop12h 15m

$714

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Sun 7/26

11:00 pm-11:39 pm

1 stop19h 39m

Chicago O'Hare Intl

Wed 8/19

6:00 am-3:09 pm

1 stop14h 09m

$717

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Wed 3/18

4:00 pm-5:54 pm

2 stops20h 54m

Chicago Midway

Mon 3/23

6:34 pm-11:30 am

2 stops21h 56m

$735

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Sat 3/14

10:00 am-5:55 am

1 stop14h 55m

Chicago Midway

Wed 3/18

5:45 am-12:35 pm

1 stop11h 50m

$759

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/24

Showing 1-10 of 37 resultsSorted by cheapest first
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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*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust 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 27, 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 February 27, 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?

    Alaska Airlines, American Airlines, and Southwest can get you from Kahului to Chicago in just under 10h 44m. Your travel time can differ by up to 4h 36m. 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 $1,197, our data indicates the cheapest price to be $232. The most popular route (Kahului - Chicago O'Hare Intl), is priced around $631.

  • 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

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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 February 27, 2026.
AirlineCheapestAverageFlexibilityOn-time
Hawaiian AirlinesCheapest$322Average$715FlexibilityNo cancel feeOn-time85%
American AirlinesCheapest$455Average$733FlexibilityNo cancel feeOn-time71%
Alaska AirlinesCheapest$468Average$715FlexibilityNo cancel feeOn-time75%

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