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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 2/9. Fares are subject to change and may not be available on all flights or dates of travel.
OGG — CHI
Dec 24 — Dec 311
Wed 12/24
Wed 12/31
1 adult, Economy
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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 November 24, 2025.

This Delta deal was found by Cheapflights users on 11/24. 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.
Tue 12/1610:00 pmOGG - ORD
1 stop11h 33mDelta
Wed 12/316:45 amORD - OGG
1 stop12h 39mDelta
Deal found 11/24$432
This Delta deal was found by Cheapflights users on 11/24. 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 12/185:10 pmOGG - ORD
1 stop11h 29mDelta
Wed 12/316:45 amORD - OGG
1 stop12h 39mDelta
Deal found 11/24$461
This Delta deal was found by Cheapflights users on 11/24. 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.
Tue 12/1610:00 pmOGG - ORD
1 stop11h 33mDelta
Tue 12/307:25 amORD - OGG
1 stop16h 01mDelta
Deal found 11/24$473
This Delta deal was found by Cheapflights users on 11/24. 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.
Sat 12/2011:40 pmOGG - ORD
1 stop14h 20mDelta
Wed 12/316:45 amORD - OGG
1 stop12h 39mDelta
Deal found 11/24$493
This Delta deal was found by Cheapflights users on 11/24. 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 12/185:10 pmOGG - MDW
1 stop12h 44mDelta
Wed 12/316:00 amMDW - OGG
1 stop13h 24mDelta
Deal found 11/24$502
This Delta deal was found by Cheapflights users on 11/24. 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 12/185:10 pmOGG - ORD
1 stop11h 29mDelta
Tue 12/307:25 amORD - OGG
1 stop16h 01mDelta
Deal found 11/24$502
This Alaska Airlines deal was found by Cheapflights users on 11/24. 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 12/1810:38 amOGG - ORD
2 stops14h 24mAlaska Airlines
Wed 12/318:39 amORD - OGG
1 stop16h 58mAlaska Airlines
Deal found 11/24$519
This Kiwi.com deal was found by Cheapflights users on 11/24. 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 12/167:45 pmOGG - ORD
2 stops30h 20mMultiple Airlines
Wed 12/316:02 pmORD - OGG
1 stop22h 25mMultiple Airlines
Deal found 11/24$523
This Alaska Airlines deal was found by Cheapflights users on 11/24. 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 12/1911:59 pmOGG - ORD
1 stop20h 00mAlaska Airlines
Wed 12/318:39 amORD - OGG
1 stop16h 58mAlaska Airlines
Deal found 11/24$527
This Delta deal was found by Cheapflights users on 11/24. 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 12/1710:00 pmOGG - ORD
1 stop11h 33mDelta
Wed 12/316:35 amORD - OGG
2 stops16h 51mDelta
Deal found 11/24$528
This Delta deal was found by Cheapflights users on 11/24. 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.
Sat 12/2011:40 pmOGG - ORD
1 stop14h 20mDelta
Tue 12/307:25 amORD - OGG
1 stop16h 01mDelta
Deal found 11/24$534
This Delta deal was found by Cheapflights users on 11/24. 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 12/225:05 pmOGG - MDW
1 stop12h 00mDelta
Tue 12/306:00 amMDW - OGG
1 stop13h 24mDelta
Deal found 11/24$543

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 November 24, 2025.

Round-trip from

$372
(Kiwi.com)

One-way from

$181
(Kiwi.com)

Good round-trip deal

$350 or less

Good one-way deal

$371 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 November 24, 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 1/15

11:59 pm-2:29 pm

1 stop10h 30m

Chicago O'Hare Intl

Thu 1/22

9:00 am-10:59 pm

1 stop17h 59m

$372

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Mon 3/2

11:54 pm-2:58 pm

1 stop11h 04m

Chicago O'Hare Intl

Wed 3/4

3:07 pm-11:46 pm

1 stop12h 39m

$382

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Mon 3/2

7:48 pm-2:58 pm

2 stops15h 10m

Chicago O'Hare Intl

Wed 3/4

3:07 pm-11:46 pm

1 stop12h 39m

$387

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Thu 1/15

9:05 pm-4:44 pm

2 stops15h 39m

Chicago O'Hare Intl

Thu 1/22

7:30 am-7:15 pm

2 stops15h 45m

$392

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Thu 1/15

2:02 pm-8:52 am

2 stops14h 50m

Chicago Midway

Thu 1/22

6:00 am-3:37 pm

1 stop13h 37m

$425

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Thu 1/15

9:35 pm-1:45 pm

1 stop12h 10m

Chicago Midway

Thu 1/22

5:05 am-12:50 pm

1 stop11h 45m

$469

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Thu 12/18

5:10 pm-9:54 am

1 stop12h 44m

Chicago Midway

Wed 12/31

6:00 am-3:24 pm

1 stop13h 24m

$502

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Fri 12/19

11:59 pm-11:59 pm

1 stop20h 00m

Chicago O'Hare Intl

Wed 12/31

8:39 am-9:37 pm

1 stop16h 58m

$527

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Wed 12/17

10:00 pm-1:33 pm

1 stop11h 33m

Chicago O'Hare Intl

Wed 12/31

6:35 am-7:26 pm

2 stops16h 51m

$528

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Mon 3/2

5:00 pm-9:58 am

1 stop12h 58m

Chicago Midway

Wed 3/4

12:46 pm-12:30 pm

2 stops27h 44m

$529

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/23

Showing 1-10 of 35 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 November 24, 2025.

A simple way to save on the total cost of your ticket is to fly from Maui to Chicago in the evening. If you’re flexible enough to do this you can expect to save up to 13% on your trip compared to booking a flight in the afternoon.

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 30m. Fly via Hawaiian Airlines, 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 Delta. According to our data, you can fly for as low as $190. Users have also found prices from $190 and $190 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 $251. On average you can expect to pay $679. The most popular route, (Kahului - Chicago O'Hare Intl), can usually be booked for $362.

  • 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
Hammond
Porter
Benton Harbor
Merrillville

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 November 24, 2025.
AirlineCheapestAverageFlexibilityOn-time
Hawaiian AirlinesCheapest$322Average$715FlexibilityNo cancel feeOn-time85%
United AirlinesCheapest$432Average$902FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$455Average$729FlexibilityNo cancel feeOn-time71%
Alaska AirlinesCheapest$468Average$635FlexibilityNo cancel feeOn-time75%

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