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$172+ 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 2/2. Fares are subject to change and may not be available on all flights or dates of travel.
OGG — CHI
Jan 17 — Jan 241
Sat 1/17
Sat 1/24
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 18, 2025.

This Southwest deal was found by Cheapflights users on 12/17. 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 12/179:35 pmOGG - MDW
1 stop11h 30mSouthwest
Sun 12/215:40 amMDW - OGG
1 stop11h 45mSouthwest
Deal found 12/17$859
This Alaska Airlines deal was found by Cheapflights users on 12/17. 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 12/1711:59 pmOGG - ORD
1 stop10h 38mAlaska Airlines
Sun 12/218:39 amORD - OGG
1 stop16h 58mAlaska Airlines
Deal found 12/17$879
This Alaska Airlines deal was found by Cheapflights users on 12/17. 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 12/1711:59 pmOGG - ORD
1 stop10h 38mAlaska Airlines
Mon 12/228:39 amORD - OGG
1 stop16h 58mAlaska Airlines
Deal found 12/17$994
This Delta deal was found by Cheapflights users on 12/17. 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 12/178:59 pmOGG - ORD
2 stops14h 21mDelta
Mon 12/222:15 pmORD - OGG
1 stop32h 03mDelta
Deal found 12/17$1,035
This Delta deal was found by Cheapflights users on 12/17. 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
Sun 12/217:25 amORD - OGG
2 stops18h 14mDelta
Deal found 12/17$1,126
This Delta deal was found by Cheapflights users on 12/17. 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 12/171:55 pmOGG - MDW
2 stops15h 24mDelta
Mon 12/226:00 amMDW - OGG
1 stop13h 24mDelta
Deal found 12/17$1,251

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 18, 2025.

Round-trip from

$343
(Alaska Airlines)

One-way from

$172
(Alaska Airlines)

Good round-trip deal

$554 or less

Good one-way deal

$292 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 18, 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 1/13

11:59 pm-11:37 pm

1 stop19h 38m

Chicago O'Hare Intl

Tue 1/20

9:00 am-10:59 pm

1 stop17h 59m

$343

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Thu 1/15

11:59 pm-2:29 pm

1 stop10h 30m

Chicago O'Hare Intl

Mon 1/19

9:00 am-10:59 pm

1 stop17h 59m

$361

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Tue 1/13

4:05 pm-2:29 pm

2 stops18h 24m

Chicago O'Hare Intl

Tue 1/20

9:00 am-10:59 pm

1 stop17h 59m

$369

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Thu 1/15

9:00 pm-2:29 pm

2 stops13h 29m

Chicago O'Hare Intl

Mon 1/19

9:00 am-10:59 pm

1 stop17h 59m

$388

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Wed 2/18

11:54 pm-11:59 pm

1 stop20h 05m

Chicago O'Hare Intl

Sun 2/22

8:20 am-11:46 pm

1 stop19h 26m

$393

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Wed 2/18

11:54 pm-11:59 pm

1 stop20h 05m

Chicago O'Hare Intl

Sun 2/22

8:20 am-10:21 pm

2 stops18h 01m

$420

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Thu 1/15

5:10 pm-1:08 pm

2 stops15h 58m

Chicago O'Hare Intl

Mon 1/19

5:30 am-7:15 pm

2 stops17h 45m

$432

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Wed 5/13

1:50 pm-5:13 am

1 stop10h 23m

Chicago O'Hare Intl

Wed 5/20

7:15 am-9:09 pm

1 stop18h 54m

$479

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Sat 2/28

6:20 pm-2:58 pm

2 stops16h 38m

Chicago O'Hare Intl

Sun 3/8

8:20 am-10:46 pm

1 stop19h 26m

$520

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Sat 2/28

11:54 pm-2:58 pm

1 stop11h 04m

Chicago O'Hare Intl

Sun 3/8

3:07 pm-10:46 pm

1 stop12h 39m

$534

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/16

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 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 18, 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 12% 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 12h 20m. Fly via Alaska Airlines, Southwest, 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 Southwest. According to our data, you can fly for as low as $210. Users have also found prices from $211 and $230 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 $783. The most popular route, (Kahului - Chicago O'Hare Intl), can usually be booked for $369.

  • 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

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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 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
Hawaiian AirlinesCheapest$322Average$715FlexibilityNo cancel feeOn-time85%
United AirlinesCheapest$424Average$963FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$455Average$733FlexibilityNo cancel feeOn-time71%
Alaska AirlinesCheapest$468Average$635FlexibilityNo cancel feeOn-time75%

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