HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$234+ 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 5/14. Fares are subject to change and may not be available on all flights or dates of travel.
OGG — CHI
Mar 19 — Mar 261
Wed 3/19
Wed 3/26
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Kahului to Chicago with Cheapflights

1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”
2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.
3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 March 14, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$533
(Alaska Airlines)

One-way from

$234
(American Airlines)

Popular in

June

Cheapest in

January

Average price

$557

Good round-trip deal

$559 or less

Good one-way deal

$315 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
Highest demand for flights based on searches. 20% potential increase in price ($150 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($25 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 2025
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

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 March 14, 2025.

This Alaska Airlines deal was found by Cheapflights users on 3/13. 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 8/1510:30 amOGG - ORD
1 stop26h 48mAlaska Airlines
Thu 8/215:50 pmORD - OGG
1 stop20h 25mAlaska Airlines
Deal found 3/13$533
This Southwest deal was found by Cheapflights users on 3/13. 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 8/1510:05 amOGG - MDW
2 stops14h 05mSouthwest
Thu 8/215:35 amMDW - OGG
1 stop12h 25mSouthwest
Deal found 3/13$689
This Delta deal was found by Cheapflights users on 3/13. 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 6/59:01 pmOGG - ORD
2 stops16h 19mDelta
Thu 7/248:55 amORD - OGG
2 stops16h 42mDelta
Deal found 3/13$772
This Southwest deal was found by Cheapflights users on 3/12. 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 4/116:00 amOGG - ORD
2 stops12h 40mSouthwest
Sat 4/196:15 amORD - OGG
2 stops15h 30mSouthwest
Deal found 3/12$819
This United Airlines deal was found by Cheapflights users on 3/13. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/118:00 amOGG - ORD
1 stop17h 25mUnited Airlines
Thu 4/179:50 pmORD - OGG
2 stops19h 06mUnited Airlines
Deal found 3/13$917
This United deal was found by Cheapflights users on 3/13. 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 United is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/165:10 pmOGG - ORD
Nonstop7h 55mMultiple Airlines
Sat 8/235:50 pmORD - OGG
1 stop20h 25mMultiple Airlines
Deal found 3/13$983
This Delta deal was found by Cheapflights users on 3/12. 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.
Fri 4/118:57 pmOGG - MDW
2 stops16h 36mDelta
Thu 4/176:04 amMDW - OGG
2 stops18h 37mDelta
Deal found 3/12$1,359

Find flights from Kahului to Chicago within your budget

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 14, 2025.

Fly from

Kahului

Fly to

Chicago

Route

Depart

Return

Price

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Fri 8/15

10:30 am-6:18 pm

1 stop26h 48m

Chicago O'Hare Intl

Thu 8/21

5:50 pm-9:15 am

1 stop20h 25m

$533

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Fri 8/15

10:05 am-5:10 am

2 stops14h 05m

Chicago Midway

Thu 8/21

5:35 am-1:00 pm

1 stop12h 25m

$689

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Thu 6/5

9:01 pm-6:20 pm

2 stops16h 19m

Chicago O'Hare Intl

Thu 7/24

8:55 am-8:37 pm

2 stops16h 42m

$772

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Fri 4/11

6:00 am-11:40 pm

2 stops12h 40m

Chicago O'Hare Intl

Sat 4/19

6:15 am-4:45 pm

2 stops15h 30m

$819

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Fri 4/11

8:00 am-6:25 am

1 stop17h 25m

Chicago O'Hare Intl

Thu 4/17

9:50 pm-11:56 am

2 stops19h 06m

$917

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Sat 8/16

5:10 pm-6:05 am

Nonstop7h 55m

Chicago O'Hare Intl

Sat 8/23

5:50 pm-9:15 am

1 stop20h 25m

$983

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Fri 4/11

8:57 pm-6:33 pm

2 stops16h 36m

Chicago Midway

Thu 4/17

6:04 am-7:41 pm

2 stops18h 37m

$1,359

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Tue 5/20

9:20 pm-1:30 pm

1 stop11h 10m

$234

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Mon 5/19

9:46 pm-11:56 pm

1 stop21h 10m

$236

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Thu 5/15

1:49 pm-5:10 am

1 stop10h 21m

$262

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/13

Showing 1-10 of 14 results
1
2

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
eDreamsPrice 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.

Travel insights for flights from Kahului to Chicago

Get recent, data-driven insights about flights from Kahului to Chicago including ideal travel times, pricing trends, and more.

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 $327). 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 March 14, 2025.

It’s optimal to fly from Kahului to Chicago in the evening. By choosing this option you can save up to 25% on the cost of your flight, compared to a flight in the afternoon.

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 14, 2025.

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).

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 March 14, 2025.
To help decide which airline to fly from Kahului to Chicago, see what other customers have to say about Southwest, Alaska Airlines and Delta. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,292 reviews

Overall

8.1

Boarding

8.2

Food

7.1

Comfort

8.1

Crew

8.7

Entertainment

7.6

Reviews

1 / 20

8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

Southwest
8.1
Very good
4,292 reviews
Southwest
8.1
Very good
4,292 reviews

Overall

8.1

Boarding

8.2

Food

7.1

Comfort

8.1

Crew

8.7

Entertainment

7.6

Reviews

1 / 20

8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

Alaska Airlines
8.0
Very good
9,734 reviews
Southwest
8.1
Very good
4,292 reviews

Overall

8.1

Boarding

8.2

Food

7.1

Comfort

8.1

Crew

8.7

Entertainment

7.6

Reviews

1 / 20

8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

Delta
8.0
Very good
7,944 reviews
Southwest
8.1
Very good
4,292 reviews

Overall

8.1

Boarding

8.2

Food

7.1

Comfort

8.1

Crew

8.7

Entertainment

7.6

Reviews

1 / 20

8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

United Airlines
7.4
Good
8,623 reviews
Southwest
8.1
Very good
4,292 reviews

Overall

8.1

Boarding

8.2

Food

7.1

Comfort

8.1

Crew

8.7

Entertainment

7.6

Reviews

1 / 20

8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

American Airlines
7.2
Good
10,000 reviews
Southwest
8.1
Very good
4,292 reviews

Overall

8.1

Boarding

8.2

Food

7.1

Comfort

8.1

Crew

8.7

Entertainment

7.6

Reviews

1 / 20

8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

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 4 different airlines.

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

    Currently priced at $533, Alaska Airlines will fly you from Kahului to Chicago and back. In addition to Alaska Airlines, many other airlines offer competitively priced options for your trip. Search Cheapflights for deals from Southwest and Delta - these airlines can fly you to your destination from $695 and $772, respectively. Alaska Airlines is priced at 6% 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?

    $234 is the cheapest one-way deal found within the past few days, from American Airlines. You may also be able to find cheap deals on Alaska Airlines and Delta, with prices starting from $246 and $262, 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 $1,208, our data indicates the cheapest price to be $239. The most popular route (Kahului - Chicago O'Hare Intl), is priced around $541.

  • 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 $327). 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
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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 March 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$312Average$541FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$349Average$538FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$432Average$739FlexibilityNo cancel feeOn-time69%
Alaska AirlinesCheapest$495Average$791FlexibilityNo cancel feeOn-time75%
100% Free
Cheapflights is completely free to use, so you can start saving the moment you arrive.
Book with Flexibility
Our users can plan ahead with confidence and find flights with no change fees
Travel Smart
Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.