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$189+ Cheap flights from Maui 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 11/5. Fares are subject to change and may not be available on all flights or dates of travel.
OGG — CHI
Aug 22 — Aug 291
Fri 8/22
Fri 8/29
1 adult, Economy
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Cheap flight deals from Maui to Chicago

Keep the following information in mind while searching for Maui to Chicago flight deals. Data was last updated August 17, 2025.

Round-trip from

$423
(Alaska Airlines)

One-way from

$189
(Alaska Airlines)

Good one-way deal

$517 or less
From Maui to Chicago (CHI)
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One-way flight from Maui to Chicago (CHI)
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Price to beat on a one-way flight from Maui to Chicago (CHI).
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Find flight deals from Maui to Chicago

Cheapest flights from Maui to Chicago
Explore the most affordable flight options available from Maui to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 17, 2025.

This Alaska Airlines deal was found by Cheapflights users on 8/15. 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.
Wed 10/1511:09 pmOGG - ORD
1 stop14h 50mAlaska Airlines
Mon 10/208:20 amORD - OGG
1 stop18h 45mAlaska Airlines
Deal found 8/15$423
This Alaska Airlines deal was found by Cheapflights users on 8/16. 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 9/168:00 amOGG - ORD
1 stop11h 03mAlaska Airlines
Mon 9/227:00 amORD - OGG
1 stop18h 39mAlaska Airlines
Deal found 8/16$461
This Alaska Airlines deal was found by Cheapflights users on 8/15. 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 10/711:09 pmOGG - ORD
1 stop10h 41mAlaska Airlines
Mon 10/137:59 pmORD - OGG
1 stop31h 06mAlaska Airlines
Deal found 8/15$482
This Kiwi.com deal was found by Cheapflights users on 8/16. 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.
Tue 9/1611:20 amOGG - ORD
2 stops29h 12mMultiple Airlines
Mon 9/227:09 pmORD - OGG
1 stop19h 36mMultiple Airlines
Deal found 8/16$498
This Delta deal was found by Cheapflights users on 8/16. 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 11/128:59 pmOGG - ORD
2 stops17h 39mDelta
Sun 11/166:00 amORD - OGG
2 stops15h 56mDelta
Deal found 8/16$513
This Alaska Airlines deal was found by Cheapflights users on 8/16. 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 11/136:00 amOGG - ORD
2 stops14h 24mAlaska Airlines
Sun 11/169:20 amORD - OGG
2 stops16h 45mAlaska Airlines
Deal found 8/16$519
This Southwest deal was found by Cheapflights users on 8/16. 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 9/168:30 pmOGG - ORD
2 stops15h 15mSouthwest
Mon 9/226:15 amORD - OGG
2 stops13h 20mSouthwest
Deal found 8/16$543
This Trip.com deal was found by Cheapflights users on 8/15. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/2811:09 pmOGG - ORD
1 stop19h 06mMultiple Airlines
Thu 10/26:20 amORD - OGG
1 stop12h 05mMultiple Airlines
Deal found 8/15$556
This Alaska Airlines deal was found by Cheapflights users on 8/15. 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 9/2810:38 pmOGG - ORD
1 stop27h 25mAlaska Airlines
Thu 10/21:01 pmORD - OGG
2 stops14h 10mAlaska Airlines
Deal found 8/15$612
This Delta deal was found by Cheapflights users on 8/15. 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 8/2812:52 pmOGG - MDW
2 stops14h 58mDelta
Wed 9/36:00 amMDW - OGG
2 stops14h 48mDelta
Deal found 8/15$979
This Delta deal was found by Cheapflights users on 8/17. 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 9/112:22 pmOGG - MDW
2 stops15h 13mDelta
Fri 9/56:00 amMDW - OGG
2 stops14h 13mDelta
Deal found 8/17$992
This Delta deal was found by Cheapflights users on 8/15. 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 10/151:30 pmOGG - MDW
2 stops14h 25mDelta
Mon 10/209:20 amMDW - OGG
2 stops13h 58mDelta
Deal found 8/15$1,066

Cheapflights Fare Finder

 
Customize your flight search to find flights from Maui 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 August 17, 2025.
Use the filters below to find and compare flights from Maui to Chicago that are best for you.

Fly from

Maui

Fly to

Chicago

Route

Depart

Return

Price

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Wed 10/15

11:09 pm-6:59 pm

1 stop14h 50m

Chicago O'Hare Intl

Mon 10/20

8:20 am-10:05 pm

1 stop18h 45m

$423

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Wed 11/12

11:59 pm-6:59 pm

1 stop15h 00m

Chicago O'Hare Intl

Sun 11/16

7:59 pm-10:50 pm

1 stop30h 51m

$423

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Thu 11/13

11:59 pm-1:54 pm

1 stop9h 55m

Chicago O'Hare Intl

Sun 11/16

7:59 pm-10:50 pm

1 stop30h 51m

$423

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Tue 9/16

8:00 am-12:03 am

1 stop11h 03m

Chicago O'Hare Intl

Mon 9/22

7:00 am-8:39 pm

1 stop18h 39m

$461

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Tue 10/7

11:09 pm-2:50 pm

1 stop10h 41m

Chicago O'Hare Intl

Mon 10/13

7:59 pm-10:05 pm

1 stop31h 06m

$482

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Tue 9/16

11:20 am-9:32 pm

2 stops29h 12m

Chicago O'Hare Intl

Mon 9/22

7:09 pm-9:45 am

1 stop19h 36m

$498

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Wed 11/12

8:59 pm-6:38 pm

2 stops17h 39m

Chicago O'Hare Intl

Sun 11/16

6:00 am-5:56 pm

2 stops15h 56m

$513

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Tue 9/16

8:30 pm-4:45 pm

2 stops15h 15m

Chicago O'Hare Intl

Mon 9/22

6:15 am-2:35 pm

2 stops13h 20m

$543

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Thu 8/28

12:52 pm-8:50 am

2 stops14h 58m

Chicago Midway

Wed 9/3

6:00 am-3:48 pm

2 stops14h 48m

$979

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Mon 9/1

12:22 pm-8:35 am

2 stops15h 13m

Chicago Midway

Fri 9/5

6:00 am-3:13 pm

2 stops14h 13m

$992

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/15

Showing 1-10 of 27 results
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Best time to book a flight from Maui to Chicago

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

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

Currently, August is the cheapest month in which you can book a flight from Maui to Chicago (average of $245). Flying from Maui 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 FUK to CHI?

Find hourly flight availability from Maui 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 August 17, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Maui to Chicago as you normally would.

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 August 17, 2025.
Peruse reviews from past customers who have flown with United Airlines and American Airlines from Maui to Chicago to help guide your decision. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
8,919 reviews

Crew

8.1

Food

6.6

Comfort

7.3

Entertainment

7.1

Overall

7.4

Boarding

7.7

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!
United Airlines
7.4
Good
8,919 reviews
United Airlines
7.4
Good
8,919 reviews

Crew

8.1

Food

6.6

Comfort

7.3

Entertainment

7.1

Overall

7.4

Boarding

7.7

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!
American Airlines
7.2
Good
10,000 reviews
United Airlines
7.4
Good
8,919 reviews

Crew

8.1

Food

6.6

Comfort

7.3

Entertainment

7.1

Overall

7.4

Boarding

7.7

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!

Related info for your journey

Find useful and relevant information for your journey from Maui to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

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

    For one-way options, check prices for Alaska Airlines. According to our data, you can fly for as low as $189. Users have also found prices from $194 and $276 on Hawaiian Airlines and Southwest, respectively.

  • What are the cheapest flights from Maui to Chicago?

    The cheapest flight price from Maui to Chicago is $501. On average you can expect to pay $606. The most popular route, (Kahului - Chicago O'Hare Intl), can usually be booked for $409.

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

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

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

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

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

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

    Currently, August is the cheapest month in which you can book a flight from Maui to Chicago (average of $245). Flying from Maui 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 Chicago?

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

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Top 4 airlines flying from Maui to Chicago

Discover the top 4 airlines that operate flights from Maui 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 August 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
Hawaiian AirlinesCheapest$322Average$715FlexibilityNo cancel feeOn-time85%
American AirlinesCheapest$349Average$455FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$432Average$847FlexibilityNo cancel feeOn-time69%
Alaska AirlinesCheapest$468Average$637FlexibilityNo cancel feeOn-time75%

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