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$175+ 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 3/25. Fares are subject to change and may not be available on all flights or dates of travel.
OGG — CHI
Jan 26 — Feb 21
Mon 1/26
Mon 2/2
1 adult, Economy
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Cheap 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 December 27, 2025.

This Alaska Airlines deal was found by Cheapflights users on 12/26. 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 12/313:52 pmOGG - ORD
1 stop18h 45mAlaska Airlines
Tue 1/63:37 pmORD - OGG
1 stop26h 59mAlaska Airlines
Deal found 12/26$762
This Alaska Airlines deal was found by Cheapflights users on 12/26. 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 12/313:52 pmOGG - ORD
1 stop18h 45mAlaska Airlines
Mon 1/58:58 pmORD - OGG
1 stop21h 54mAlaska Airlines
Deal found 12/26$763
This Alaska Airlines deal was found by Cheapflights users on 12/26. 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 12/313:52 pmOGG - ORD
1 stop18h 45mMultiple Airlines
Tue 1/68:39 amORD - OGG
2 stops17h 37mMultiple Airlines
Deal found 12/26$768
This Alaska Airlines deal was found by Cheapflights users on 12/26. 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 12/313:52 pmOGG - ORD
1 stop18h 45mMultiple Airlines
Mon 1/56:00 amORD - OGG
2 stops16h 01mMultiple Airlines
Deal found 12/26$788
This Southwest deal was found by Cheapflights users on 12/27. 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 12/319:25 pmOGG - ORD
1 stop12h 05mSouthwest
Mon 1/57:15 amORD - OGG
2 stops13h 20mSouthwest
Deal found 12/27$798
This United Airlines deal was found by Cheapflights users on 12/26. 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.
Wed 12/3110:45 pmOGG - ORD
1 stop16h 10mUnited Airlines
Mon 1/59:20 amORD - OGG
Nonstop9h 24mUnited Airlines
Deal found 12/26$1,272
This United Airlines deal was found by Cheapflights users on 12/26. 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.
Wed 12/315:15 pmOGG - ORD
Nonstop7h 59mUnited Airlines
Tue 1/612:45 pmORD - OGG
1 stop12h 01mUnited Airlines
Deal found 12/26$1,294

Find flight deals from Maui to Chicago

Keep the following information in mind while searching for Maui to Chicago flight deals. Data was last updated December 27, 2025.

Round-trip from

$411
(Alaska Airlines)

One-way from

$175
(Kiwi.com)

Good round-trip deal

$485 or less

Good one-way deal

$242 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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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 December 27, 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

Thu 1/29

11:59 pm-11:37 pm

1 stop19h 38m

Chicago O'Hare Intl

Tue 2/3

9:00 am-10:59 pm

1 stop17h 59m

$411

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Thu 1/22

11:59 pm-2:29 pm

1 stop10h 30m

Chicago O'Hare Intl

Sun 1/25

6:06 pm-11:20 pm

1 stop33h 14m

$417

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Thu 1/29

11:59 pm-2:29 pm

1 stop10h 30m

Chicago O'Hare Intl

Tue 2/3

3:44 pm-10:40 am

2 stops22h 56m

$418

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Thu 1/29

10:00 pm-5:44 pm

2 stops15h 44m

Chicago O'Hare Intl

Tue 2/3

7:05 am-7:15 pm

2 stops16h 10m

$451

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Wed 2/18

11:54 pm-11:59 pm

1 stop20h 05m

Chicago O'Hare Intl

Sun 2/22

3:07 pm-2:40 pm

2 stops27h 33m

$472

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Sat 1/24

9:00 pm-2:29 pm

2 stops13h 29m

Chicago O'Hare Intl

Sat 1/31

3:44 pm-10:59 pm

1 stop35h 15m

$478

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Sat 1/24

11:59 pm-2:29 pm

1 stop10h 30m

Chicago O'Hare Intl

Sat 1/31

3:44 pm-10:59 pm

1 stop35h 15m

$499

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Thu 1/22

9:00 pm-5:10 pm

2 stops16h 10m

Chicago O'Hare Intl

Sun 1/25

8:00 am-6:06 pm

2 stops14h 06m

$568

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Thu 1/8

11:55 am-9:32 pm

1 stop29h 37m

Chicago O'Hare Intl

Mon 1/12

10:37 pm-12:29 pm

2 stops41h 52m

$723

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Sun 1/11

11:59 pm-2:29 pm

1 stop10h 30m

Chicago O'Hare Intl

Thu 1/15

3:44 pm-2:36 pm

1 stop26h 52m

$726

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/25

Showing 1-10 of 29 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, November is the cheapest month in which you can book a flight from Maui to Chicago (average of $222). Flying from Maui to Chicago in February is currently the most expensive (average of $812). 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 December 27, 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.

Weekly flight availability from Maui to Chicago

Explore weekly flight availability from Maui 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 December 27, 2025.

The most flights from zzFUK 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).

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 44m. Fly via Alaska Airlines or Delta to get the fastest option. The distance from Maui to Chicago is about 4175 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 Southwest. According to our data, you can fly for as low as $210. Users have also found prices from $211 and $212 on Delta and American 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 $780. The most popular route, (Kahului - Chicago O'Hare Intl), can usually be booked for $388.

  • 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, November is the cheapest month in which you can book a flight from Maui to Chicago (average of $222). Flying from Maui to Chicago in February is currently the most expensive (average of $812). 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
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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 December 27, 2025.
AirlineCheapestAverageFlexibilityOn-time
Hawaiian AirlinesCheapest$322Average$715FlexibilityNo cancel feeOn-time85%
American AirlinesCheapest$455Average$733FlexibilityNo cancel feeOn-time71%
Alaska AirlinesCheapest$468Average$635FlexibilityNo cancel feeOn-time75%
United AirlinesCheapest$793Average$1,193FlexibilityNo cancel feeOn-time69%

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