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$180+ 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 12/11. Fares are subject to change and may not be available on all flights or dates of travel.
OGG — CHI
Dec 6 — Dec 131
Sat 12/6
Sat 12/13
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 6, 2025.

This Alaska Airlines deal was found by Cheapflights users on 11/5. 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 12/183:52 pmOGG - ORD
1 stop24h 10mAlaska Airlines
Sun 1/48:58 pmORD - OGG
1 stop28h 39mAlaska Airlines
Deal found 11/5$383
This Delta deal was found by Cheapflights users on 11/5. 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 11/2610:20 pmOGG - ORD
1 stop11h 26mDelta
Sun 11/305:23 amORD - OGG
1 stop14h 05mDelta
Deal found 11/5$464
This Delta deal was found by Cheapflights users on 11/5. 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 12/181:55 pmOGG - ORD
2 stops14h 45mDelta
Sun 1/47:25 amORD - OGG
2 stops14h 53mDelta
Deal found 11/5$535
This Orbitz deal was found by Cheapflights users on 11/5. 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 Orbitz 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
Sun 1/48:00 amORD - OGG
2 stops18h 16mAlaska Airlines
Deal found 11/5$554
This Kiwi.com deal was found by Cheapflights users on 11/5. 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.
Fri 12/194:07 pmOGG - ORD
2 stops19h 53mMultiple Airlines
Sun 1/410:49 pmORD - OGG
1 stop17h 49mMultiple Airlines
Deal found 11/5$557
This Delta deal was found by Cheapflights users on 11/5. 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.
Fri 12/1911:40 pmOGG - ORD
2 stops14h 44mDelta
Sun 1/47:25 amORD - OGG
2 stops14h 53mDelta
Deal found 11/5$565
This Alaska Airlines deal was found by Cheapflights users on 11/5. 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 11/2011:15 amOGG - ORD
2 stops13h 46mAlaska Airlines
Wed 11/268:20 amORD - OGG
1 stop17h 10mAlaska Airlines
Deal found 11/5$638
This Kiwi.com deal was found by Cheapflights users on 11/5. 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.
Fri 11/214:03 pmOGG - ORD
1 stop28h 56mMultiple Airlines
Tue 11/258:39 pmORD - OGG
2 stops43h 44mMultiple Airlines
Deal found 11/5$661
This Kiwi.com deal was found by Cheapflights users on 11/4. 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.
Thu 11/203:52 pmOGG - ORD
2 stops35h 51mMultiple Airlines
Mon 11/248:18 pmORD - OGG
1 stop20h 05mMultiple Airlines
Deal found 11/4$694
This Southwest deal was found by Cheapflights users on 11/5. 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 11/209:25 pmOGG - MDW
1 stop11h 05mSouthwest
Wed 11/265:00 amMDW - OGG
1 stop11h 25mSouthwest
Deal found 11/5$738
This Delta deal was found by Cheapflights users on 11/5. 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.
Fri 11/215:10 pmOGG - MDW
1 stop12h 43mDelta
Tue 11/259:34 amMDW - OGG
2 stops14h 33mDelta
Deal found 11/5$911
This Delta deal was found by Cheapflights users on 11/4. 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 11/205:10 pmOGG - MDW
1 stop12h 42mDelta
Mon 11/246:00 amMDW - OGG
1 stop13h 28mDelta
Deal found 11/4$918

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 6, 2025.

Round-trip from

$383
(Alaska Airlines)

One-way from

$180
(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 6, 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 11/26

10:20 pm-1:46 pm

1 stop11h 26m

Chicago O'Hare Intl

Sun 11/30

5:23 am-3:28 pm

1 stop14h 05m

$464

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Thu 12/18

10:38 am-6:05 am

2 stops15h 27m

Chicago O'Hare Intl

Sun 1/4

10:49 pm-12:38 pm

1 stop17h 49m

$464

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Fri 12/19

11:59 pm-11:59 pm

1 stop20h 00m

Chicago O'Hare Intl

Sun 1/4

8:00 am-10:16 pm

2 stops18h 16m

$554

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Fri 12/19

4:07 pm-4:00 pm

2 stops19h 53m

Chicago O'Hare Intl

Sun 1/4

10:49 pm-12:38 pm

1 stop17h 49m

$557

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Fri 12/19

11:40 pm-6:24 pm

2 stops14h 44m

Chicago O'Hare Intl

Sun 1/4

7:25 am-6:18 pm

2 stops14h 53m

$565

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Thu 11/20

11:15 am-5:01 am

2 stops13h 46m

Chicago O'Hare Intl

Wed 11/26

8:20 am-9:30 pm

1 stop17h 10m

$638

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Fri 11/21

4:03 pm-12:59 am

1 stop28h 56m

Chicago O'Hare Intl

Tue 11/25

8:39 pm-12:23 pm

2 stops43h 44m

$661

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Thu 11/20

3:52 pm-7:43 am

2 stops35h 51m

Chicago O'Hare Intl

Mon 11/24

8:18 pm-12:23 pm

1 stop20h 05m

$694

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Wed 11/12

3:52 pm-11:44 pm

2 stops27h 52m

Chicago O'Hare Intl

Sun 11/16

9:22 pm-1:40 pm

1 stop20h 18m

$699

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Fri 11/21

1:31 pm-5:01 am

1 stop11h 30m

Chicago O'Hare Intl

Tue 11/25

8:49 pm-3:40 pm

1 stop22h 51m

$713

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/6

Showing 1-10 of 30 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 $220). Flying from Maui to Chicago in February is currently the most expensive (average of $815). 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 6, 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 11h 05m. Fly via Delta, 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 Alaska Airlines. According to our data, you can fly for as low as $183. Users have also found prices from $223 and $223 on Southwest and Delta, 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 $419.

  • 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 $220). Flying from Maui to Chicago in February is currently the most expensive (average of $815). 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

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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 6, 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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