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$181+ 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 11/24. Fares are subject to change and may not be available on all flights or dates of travel.
OGG — CHI
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
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 September 15, 2025.

Round-trip from

$421
(Alaska Airlines)

One-way from

$181
(American Airlines)

Good round-trip deal

$280 or less

Good one-way deal

$346 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 round-trip 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 September 15, 2025.

This Alaska Airlines deal was found by Cheapflights users on 9/14. 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 11/511:59 pmOGG - ORD
1 stop15h 56mAlaska Airlines
Sun 11/98:59 pmORD - OGG
1 stop29h 51mAlaska Airlines
Deal found 9/14$423
This Alaska Airlines deal was found by Cheapflights users on 9/13. 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.
Thu 10/236:00 amOGG - ORD
2 stops12h 59mAlaska Airlines
Sun 10/267:59 pmORD - OGG
1 stop22h 33mAlaska Airlines
Deal found 9/13$488
This Alaska Airlines deal was found by Cheapflights users on 9/13. 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.
Mon 10/611:09 pmOGG - ORD
1 stop19h 50mAlaska Airlines
Wed 10/158:20 amORD - OGG
1 stop18h 45mAlaska Airlines
Deal found 9/13$535
This Alaska Airlines deal was found by Cheapflights users on 9/13. 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.
Tue 10/79:45 pmOGG - ORD
1 stop26h 16mAlaska Airlines
Wed 10/158:20 amORD - OGG
1 stop18h 45mAlaska Airlines
Deal found 9/13$552
This Delta deal was found by Cheapflights users on 9/14. 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 11/51:35 pmOGG - ORD
2 stops14h 15mDelta
Sun 11/95:32 amORD - OGG
2 stops17h 49mDelta
Deal found 9/14$582
This Alaska Airlines deal was found by Cheapflights users on 9/13. 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.
Wed 10/89:45 pmOGG - ORD
1 stop26h 16mAlaska Airlines
Tue 10/147:59 pmORD - OGG
1 stop31h 06mAlaska Airlines
Deal found 9/13$611
This Kiwi.com deal was found by Cheapflights users on 9/13. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/710:50 amOGG - ORD
1 stop28h 58mMultiple Airlines
Fri 10/177:51 pmORD - OGG
2 stops42h 58mMultiple Airlines
Deal found 9/13$617
This Kiwi.com deal was found by Cheapflights users on 9/13. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/72:58 pmOGG - ORD
2 stops24h 50mMultiple Airlines
Sat 10/117:25 amORD - OGG
1 stop31h 24mMultiple Airlines
Deal found 9/13$630
This Kiwi.com deal was found by Cheapflights users on 9/13. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/72:58 pmOGG - ORD
2 stops24h 50mMultiple Airlines
Tue 10/146:40 amORD - OGG
1 stop32h 24mMultiple Airlines
Deal found 9/13$634
This Southwest deal was found by Cheapflights users on 9/13. 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.
Wed 10/88:30 pmOGG - MDW
1 stop10h 45mSouthwest
Tue 10/146:05 amMDW - OGG
1 stop11h 20mSouthwest
Deal found 9/13$748
This Southwest deal was found by Cheapflights users on 9/14. 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 9/158:30 pmOGG - MDW
1 stop10h 45mSouthwest
Mon 9/225:15 amMDW - OGG
1 stop12h 10mSouthwest
Deal found 9/14$759
This Southwest deal was found by Cheapflights users on 9/14. 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 9/188:25 pmOGG - MDW
1 stop10h 20mSouthwest
Thu 9/255:35 amMDW - OGG
1 stop12h 25mSouthwest
Deal found 9/14$769

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 September 15, 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

Tue 3/3

9:48 am-5:04 am

2 stops15h 16m

Chicago O'Hare Intl

Wed 3/4

9:00 am-10:48 pm

1 stop17h 48m

$421

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Wed 11/5

11:59 pm-7:55 pm

1 stop15h 56m

Chicago O'Hare Intl

Sun 11/9

8:59 pm-10:50 pm

1 stop29h 51m

$423

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Wed 2/11

6:00 am-11:10 pm

2 stops13h 10m

Chicago O'Hare Intl

Mon 2/16

9:00 am-10:48 pm

1 stop17h 48m

$447

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Sat 1/31

11:20 pm-1:59 pm

1 stop10h 39m

Chicago O'Hare Intl

Sat 2/7

9:00 am-10:48 pm

1 stop17h 48m

$475

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Thu 10/23

6:00 am-11:59 pm

2 stops12h 59m

Chicago O'Hare Intl

Sun 10/26

7:59 pm-1:32 pm

1 stop22h 33m

$488

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Wed 10/8

8:30 pm-12:15 pm

1 stop10h 45m

Chicago Midway

Tue 10/14

6:05 am-12:25 pm

1 stop11h 20m

$748

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Fri 12/19

9:35 pm-1:40 pm

1 stop12h 05m

Chicago Midway

Wed 12/31

5:25 am-1:05 pm

1 stop11h 40m

$813

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Fri 12/19

9:35 pm-1:40 pm

1 stop12h 05m

Chicago Midway

Tue 12/30

5:00 am-12:25 pm

1 stop11h 25m

$848

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Thu 10/9

12:26 pm-8:55 am

2 stops15h 29m

Chicago Midway

Wed 10/15

6:00 am-3:38 pm

2 stops14h 38m

$1,186

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Sat 10/11

11:55 am-8:55 am

2 stops16h 00m

Chicago Midway

Sat 10/18

9:20 am-6:18 pm

2 stops13h 58m

$1,280

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/12

Showing 1-10 of 25 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 September 15, 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 September 15, 2025.
Peruse reviews from past customers who have flown with United 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
8,931 reviews

Boarding

7.7

Food

6.6

Entertainment

7.1

Crew

8.1

Overall

7.4

Comfort

7.3

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
8,931 reviews
United Airlines
7.4
Good
8,931 reviews

Boarding

7.7

Food

6.6

Entertainment

7.1

Crew

8.1

Overall

7.4

Comfort

7.3

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.

  • How long is the flight from Maui to Chicago?

    There are many flights that can get you from Maui to Chicago in 10h 45m. Fly via Alaska Airlines or Southwest to get the fastest option. The distance from Maui to Chicago is about 4184 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

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

    For one-way options, check prices for American Airlines. According to our data, you can fly for as low as $181. Users have also found prices from $212 and $212 on Alaska Airlines and Hawaiian Airlines, respectively.

  • What are the cheapest flights from Maui to Chicago?

    The cheapest flight price from Maui to Chicago is $280. On average you can expect to pay $817. The most popular route, (Kahului - Chicago O'Hare Intl), can usually be booked for $441.

  • 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

Browse thousands of different options on Cheapflights for your next trip

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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 September 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
Hawaiian AirlinesCheapest$322Average$715FlexibilityNo cancel feeOn-time85%
American AirlinesCheapest$399Average$709FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$432Average$863FlexibilityNo cancel feeOn-time69%
Alaska AirlinesCheapest$468Average$635FlexibilityNo cancel feeOn-time75%

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