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$220+ 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 10/6. Fares are subject to change and may not be available on all flights or dates of travel.
OGG — CHI
Jul 8 — Jul 151
Tue 7/8
Tue 7/15
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 July 3, 2025.

Round-trip from

$465
(American Airlines)

One-way from

$220
(Alaska Airlines)

Popular in

June

Cheapest in

January

Average price

$711

Good one-way deal

$653 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. 23% potential increase in price ($187 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease ($33 potential savings vs. average RT price).
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Average for round-trip flights in July 2025
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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 July 3, 2025.

This American Airlines deal was found by Cheapflights users on 7/3. 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.
Wed 9/31:14 pmOGG - ORD
1 stop11h 47mAmerican Airlines
Sat 9/66:00 amORD - OGG
1 stop10h 44mAmerican Airlines
Deal found 7/3$465
This Delta deal was found by Cheapflights users on 7/3. 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.
Wed 9/39:10 pmOGG - ORD
1 stop11h 07mDelta
Sat 9/66:10 amORD - OGG
2 stops15h 58mDelta
Deal found 7/3$471
This Southwest deal was found by Cheapflights users on 7/2. 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.
Fri 8/228:30 pmOGG - MDW
1 stop15h 00mSouthwest
Sun 9/78:20 amMDW - OGG
1 stop13h 10mSouthwest
Deal found 7/2$524
This Alaska Airlines deal was found by Cheapflights users on 7/2. 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.
Sun 8/2410:38 pmOGG - ORD
1 stop27h 25mAlaska Airlines
Sat 9/612:05 pmORD - OGG
1 stop14h 33mAlaska Airlines
Deal found 7/2$550
This Southwest deal was found by Cheapflights users on 7/1. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/38:45 pmOGG - ORD
1 stop13h 35mSouthwest
Tue 8/196:15 amORD - OGG
1 stop11h 10mSouthwest
Deal found 7/1$669
This Hawaiian Airlines deal was found by Cheapflights users on 7/2. 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 Hawaiian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/2312:45 pmOGG - ORD
1 stop13h 18mHawaiian Airlines
Sun 9/76:20 amORD - OGG
1 stop12h 05mHawaiian Airlines
Deal found 7/2$685
This Delta deal was found by Cheapflights users on 7/1. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/222:10 pmOGG - MDW
2 stops13h 35mDelta
Thu 7/249:25 amMDW - OGG
2 stops15h 08mDelta
Deal found 7/1$1,120

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 July 3, 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 9/3

1:14 pm-6:01 am

1 stop11h 47m

Chicago O'Hare Intl

Sat 9/6

6:00 am-11:44 am

1 stop10h 44m

$465

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Wed 9/3

9:10 pm-1:17 pm

1 stop11h 07m

Chicago O'Hare Intl

Sat 9/6

6:10 am-5:08 pm

2 stops15h 58m

$471

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Fri 8/22

8:30 pm-4:30 pm

1 stop15h 00m

Chicago Midway

Sun 9/7

8:20 am-4:30 pm

1 stop13h 10m

$524

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Sun 8/24

10:38 pm-7:03 am

1 stop27h 25m

Chicago O'Hare Intl

Tue 9/9

2:07 pm-8:39 pm

1 stop11h 32m

$550

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Sun 8/3

8:45 pm-3:20 pm

1 stop13h 35m

Chicago O'Hare Intl

Tue 8/19

6:15 am-12:25 pm

1 stop11h 10m

$669

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Sat 8/23

12:45 pm-7:03 am

1 stop13h 18m

Chicago O'Hare Intl

Sun 9/7

6:20 am-1:25 pm

1 stop12h 05m

$685

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Tue 7/22

2:10 pm-8:45 am

2 stops13h 35m

Chicago Midway

Thu 7/24

9:25 am-7:33 pm

2 stops15h 08m

$1,120

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Mon 10/6

11:09 pm-11:59 pm

1 stop19h 50m

$220

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Wed 9/10

8:30 pm-1:25 pm

1 stop11h 55m

$233

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Wed 9/10

9:29 pm-12:31 pm

1 stop10h 02m

$233

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/3

Showing 1-10 of 15 results
1
2

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 July 3, 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.

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

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 July 3, 2025.
Read through reviews of airlines operating flights from Kahului to Chicago, such as Alaska Airlines, Southwest, and Delta. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Food

7.1

Crew

8.5

Comfort

7.8

Entertainment

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Food

7.1

Crew

8.5

Comfort

7.8

Entertainment

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Southwest
8.0
Very good
4,266 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Food

7.1

Crew

8.5

Comfort

7.8

Entertainment

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Delta
8.0
Very good
7,982 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Food

7.1

Crew

8.5

Comfort

7.8

Entertainment

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Hawaiian Airlines
7.8
Good
2,545 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Food

7.1

Crew

8.5

Comfort

7.8

Entertainment

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
United Airlines
7.4
Good
8,861 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Food

7.1

Crew

8.5

Comfort

7.8

Entertainment

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

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.

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

    Currently priced at $465, American Airlines will fly you from Kahului to Chicago and back. In addition to American Airlines, many other airlines offer competitively priced options for your trip. Search Cheapflights for deals from Delta and Southwest - these airlines can fly you to your destination from $471 and $524, respectively. American Airlines is priced at 23% 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?

    $220 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 Southwest and American Airlines, with prices starting from $233 and $233, 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 $812, our data indicates the cheapest price to be $561. The most popular route (Kahului - Chicago O'Hare Intl), is priced around $465.

  • 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 Kahului?

Book flights to Kahului if you plan to visit one of these locations
Merrillville
Lansing
Benton Harbor
Porter
Hammond
Valparaiso
Chesterton

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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 July 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
Hawaiian AirlinesCheapest$322Average$715FlexibilityNo cancel feeOn-time85%
American AirlinesCheapest$349Average$501FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$478Average$827FlexibilityNo cancel feeOn-time69%
Alaska AirlinesCheapest$508Average$715FlexibilityNo cancel feeOn-time75%

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