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$191+ 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 2/19. Fares are subject to change and may not be available on all flights or dates of travel.
OGG — CHI
Feb 13 — Feb 201
Fri 2/13
Fri 2/20
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 14, 2026.

Round-trip from

$404
(Alaska Airlines)

One-way from

$191
(Kiwi.com)

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 14, 2026.

This Alaska Airlines 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/1210:41 pm
OGG
-
ORD
1 stop15h 05m
Alaska Airlines
Wed 5/209:00 am
ORD
-
OGG
1 stop17h 30m
Alaska Airlines
Deal found 1/11$404
This Alaska Airlines deal was found by Cheapflights users on 1/12. 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 2/112:03 pm
OGG
-
ORD
1 stop29h 56m
Alaska Airlines
Wed 2/183:07 pm
ORD
-
OGG
1 stop12h 39m
Alaska Airlines
Deal found 1/12$412
This Alaska Airlines 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/1210:41 pm
OGG
-
ORD
1 stop15h 05m
Alaska Airlines
Mon 5/187:59 pm
ORD
-
OGG
1 stop30h 31m
Alaska Airlines
Deal found 1/11$413
This Expedia deal was found by Cheapflights users on 1/12. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/1111:59 pm
OGG
-
ORD
1 stop10h 59m
Multiple Airlines
Wed 2/188:20 am
ORD
-
OGG
2 stops18h 01m
Multiple Airlines
Deal found 1/12$418
This American Airlines deal was found by Cheapflights users on 1/12. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/251:46 pm
OGG
-
ORD
1 stop12h 39m
American Airlines
Mon 4/61:40 pm
ORD
-
OGG
1 stop12h 32m
American Airlines
Deal found 1/12$422
This Alaska Airlines deal was found by Cheapflights users on 1/13. 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 2/1611:54 pm
OGG
-
ORD
1 stop20h 05m
Alaska Airlines
Wed 2/183:07 pm
ORD
-
OGG
1 stop12h 39m
Alaska Airlines
Deal found 1/13$423
This Alaska Airlines deal was found by Cheapflights users on 1/13. 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 2/1611:54 pm
OGG
-
ORD
1 stop20h 05m
Multiple Airlines
Wed 2/188:20 am
ORD
-
OGG
2 stops18h 01m
Multiple Airlines
Deal found 1/13$429
This Alaska Airlines 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/129:00 pm
OGG
-
ORD
2 stops17h 03m
Multiple Airlines
Wed 5/209:00 am
ORD
-
OGG
1 stop17h 30m
Multiple Airlines
Deal found 1/11$431
This Alaska Airlines 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/1210:41 pm
OGG
-
ORD
1 stop15h 05m
Alaska Airlines
Sat 5/169:00 am
ORD
-
OGG
1 stop17h 30m
Alaska Airlines
Deal found 1/11$435
This Alaska Airlines 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/129:00 pm
OGG
-
ORD
2 stops17h 03m
Multiple Airlines
Mon 5/187:59 pm
ORD
-
OGG
1 stop30h 31m
Multiple Airlines
Deal found 1/11$441
This Alaska Airlines 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/122:37 pm
OGG
-
ORD
1 stop11h 03m
Alaska Airlines
Sun 5/177:59 pm
ORD
-
OGG
1 stop30h 31m
Alaska Airlines
Deal found 1/11$455
This Alaska Airlines 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/129:00 pm
OGG
-
ORD
2 stops17h 03m
Multiple Airlines
Sat 5/167:59 pm
ORD
-
OGG
1 stop30h 31m
Multiple Airlines
Deal found 1/11$461

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 14, 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

Wed 2/11

2:03 pm-11:59 pm

1 stop29h 56m

Chicago O'Hare Intl

Wed 2/18

3:07 pm-11:46 pm

1 stop12h 39m

$412

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Tue 5/12

10:41 pm-6:46 pm

1 stop15h 05m

Chicago O'Hare Intl

Mon 5/18

7:59 pm-9:30 pm

1 stop30h 31m

$413

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Tue 5/12

9:59 pm-2:16 pm

1 stop11h 17m

Chicago O'Hare Intl

Mon 5/18

7:00 am-1:24 pm

1 stop11h 24m

$422

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Mon 2/16

11:54 pm-11:59 pm

1 stop20h 05m

Chicago O'Hare Intl

Wed 2/18

8:20 am-10:21 pm

2 stops18h 01m

$429

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Tue 5/12

9:00 pm-7:03 pm

2 stops17h 03m

Chicago O'Hare Intl

Wed 5/20

9:00 am-9:30 pm

1 stop17h 30m

$431

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Tue 5/12

9:00 pm-7:03 pm

2 stops17h 03m

Chicago O'Hare Intl

Tue 5/19

9:00 am-9:30 pm

1 stop17h 30m

$431

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Tue 5/12

10:41 pm-6:46 pm

1 stop15h 05m

Chicago O'Hare Intl

Sat 5/16

9:00 am-9:30 pm

1 stop17h 30m

$435

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Tue 5/12

9:00 pm-7:03 pm

2 stops17h 03m

Chicago O'Hare Intl

Mon 5/18

7:59 pm-9:30 pm

1 stop30h 31m

$441

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Tue 5/12

2:37 pm-6:40 am

1 stop11h 03m

Chicago O'Hare Intl

Sun 5/17

7:59 pm-9:30 pm

1 stop30h 31m

$455

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Tue 5/12

9:00 pm-7:03 pm

2 stops17h 03m

Chicago O'Hare Intl

Sat 5/16

7:59 pm-9:30 pm

1 stop30h 31m

$461

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/12

Showing 1-10 of 34 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 14, 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.

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 January 14, 2026.

The most flights from zzFUK to CHI are scheduled on a Monday (2 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (1 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 11h 17m. Fly via Alaska Airlines, American Airlines, or Southwest 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 $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 $756. The most popular route, (Kahului - Chicago O'Hare Intl), can usually be booked for $418.

  • 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 14, 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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