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$171+ 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 3/4. Fares are subject to change and may not be available on all flights or dates of travel.
OGG — CHI
Feb 10 — Feb 171
Tue 2/10
Tue 2/17
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 January 11, 2026.

Round-trip from

$361
(SmartFares)

One-way from

$171
(Alaska Airlines)

Good round-trip deal

$447 or less

Good one-way deal

$239 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 January 11, 2026.

This SmartFares deal was found by Cheapflights users on 1/11. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/2511:08 pmOGG - ORD
1 stop11h 03mHawaiian Airlines
Wed 3/43:07 pmORD - OGG
1 stop12h 39mHawaiian Airlines
Deal found 1/11$361
This Alaska Airlines deal was found by Cheapflights users on 1/10. 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 2/911:59 pmOGG - ORD
1 stop19h 38mAlaska Airlines
Mon 2/168:20 amORD - OGG
1 stop19h 26mAlaska Airlines
Deal found 1/10$393
This SmartFares deal was found by Cheapflights users on 1/11. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/257:48 pmOGG - ORD
2 stops15h 10mMultiple Airlines
Wed 3/42:07 pmORD - OGG
1 stop11h 57mMultiple Airlines
Deal found 1/11$399
This Alaska Airlines deal was found by Cheapflights users on 1/8. 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 1/2911:59 pmOGG - ORD
1 stop10h 30mAlaska Airlines
Sun 2/12:06 pmORD - OGG
1 stop11h 54mAlaska Airlines
Deal found 1/8$419
This Alaska Airlines deal was found by Cheapflights users on 1/10. 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 2/99:00 pmOGG - ORD
2 stops22h 37mMultiple Airlines
Mon 2/168:20 amORD - OGG
1 stop19h 26mMultiple Airlines
Deal found 1/10$431
This Alaska Airlines deal was found by Cheapflights users on 1/8. 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 1/296:00 amOGG - ORD
2 stops13h 50mMultiple Airlines
Sun 2/12:06 pmORD - OGG
1 stop11h 54mMultiple Airlines
Deal found 1/8$470
This Delta deal was found by Cheapflights users on 1/11. 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 2/2510:00 pmOGG - MDW
2 stops15h 37mDelta
Wed 3/49:34 amMDW - OGG
2 stops13h 41mDelta
Deal found 1/11$574
This Delta deal was found by Cheapflights users on 1/10. 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 2/95:10 pmOGG - ORD
2 stops16h 03mDelta
Mon 2/167:40 amORD - OGG
2 stops15h 35mDelta
Deal found 1/10$585
This Kiwi.com deal was found by Cheapflights users on 1/11. 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 8/251:10 pmOGG - ORD
1 stop12h 50mMultiple Airlines
Tue 9/86:00 amORD - OGG
1 stop12h 15mMultiple Airlines
Deal found 1/11$653
This Southwest deal was found by Cheapflights users on 1/11. 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 8/258:35 pmOGG - MDW
1 stop12h 00mSouthwest
Tue 9/86:00 amMDW - OGG
2 stops12h 45mSouthwest
Deal found 1/11$670
This Delta deal was found by Cheapflights users on 1/11. 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 1/262:02 pmOGG - MDW
2 stops19h 07mDelta
Fri 1/306:00 amMDW - OGG
1 stop13h 37mDelta
Deal found 1/11$875
This Delta deal was found by Cheapflights users on 1/9. 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.
Sun 1/255:10 pmOGG - MDW
1 stop12h 43mDelta
Thu 1/296:00 amMDW - OGG
1 stop13h 37mDelta
Deal found 1/9$917

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 January 11, 2026.
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

Mon 2/9

11:59 pm-11:37 pm

1 stop19h 38m

Chicago O'Hare Intl

Mon 2/16

8:20 am-11:46 pm

1 stop19h 26m

$393

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Thu 1/29

11:59 pm-2:29 pm

1 stop10h 30m

Chicago O'Hare Intl

Sun 2/1

2:06 pm-10:00 pm

1 stop11h 54m

$419

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Mon 2/9

9:00 pm-11:37 pm

2 stops22h 37m

Chicago O'Hare Intl

Mon 2/16

8:20 am-11:46 pm

1 stop19h 26m

$431

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Thu 1/29

6:00 am-11:50 pm

2 stops13h 50m

Chicago O'Hare Intl

Sun 2/1

2:06 pm-10:00 pm

1 stop11h 54m

$470

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Wed 2/25

10:00 pm-5:37 pm

2 stops15h 37m

Chicago Midway

Wed 3/4

9:34 am-7:15 pm

2 stops13h 41m

$574

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Mon 2/9

5:10 pm-1:13 pm

2 stops16h 03m

Chicago O'Hare Intl

Mon 2/16

7:40 am-7:15 pm

2 stops15h 35m

$585

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Mon 1/26

11:59 pm-11:37 pm

1 stop19h 38m

Chicago O'Hare Intl

Fri 1/30

8:00 am-6:06 pm

2 stops14h 06m

$686

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Mon 1/26

11:59 pm-11:37 pm

1 stop19h 38m

Chicago O'Hare Intl

Fri 1/30

2:06 pm-10:00 pm

1 stop11h 54m

$695

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Sun 1/25

6:00 am-11:37 pm

2 stops13h 37m

Chicago O'Hare Intl

Thu 1/29

9:00 am-10:59 pm

1 stop17h 59m

$699

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Mon 1/26

2:02 pm-1:09 pm

2 stops19h 07m

Chicago Midway

Fri 1/30

6:00 am-3:37 pm

1 stop13h 37m

$875

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/8

Showing 1-10 of 31 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 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 January 11, 2026.

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.

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 15h 37m. Fly via Alaska Airlines or Delta 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 Delta. According to our data, you can fly for as low as $211. Users have also found prices from $212 and $232 on American Airlines and Alaska Airlines, respectively.

  • What are the cheapest flights from Maui to Chicago?

    The cheapest flight price from Maui to Chicago is $221. On average you can expect to pay $733. The most popular route, (Kahului - Chicago O'Hare Intl), can usually be booked for $350.

  • 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.

See more FAQs

Traveling to a place near Chicago?

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

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Top 3 airlines flying from Maui to Chicago

Discover the top 3 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 January 11, 2026.
AirlineCheapestAverageFlexibilityOn-time
Hawaiian AirlinesCheapest$322Average$715FlexibilityNo cancel feeOn-time85%
American AirlinesCheapest$455Average$733FlexibilityNo cancel feeOn-time71%
Alaska AirlinesCheapest$468Average$683FlexibilityNo cancel feeOn-time75%

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