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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 1/26. Fares are subject to change and may not be available on all flights or dates of travel.
OGG — CHI
Feb 1 — Feb 81
Sun 2/1
Sun 2/8
1 adult, Economy
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Cheap flight deals from Maui to Chicago

Best flights from Maui to Chicago
Discover carefully curated flight deals from Maui to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated January 2, 2026.

This Delta deal was found by Cheapflights users on 12/31. 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 1/209:05 pmOGG - ORD
1 stop12h 33mDelta
Mon 1/265:30 amORD - OGG
2 stops17h 45mDelta
Deal found 12/31$411
This Kiwi.com deal was found by Cheapflights users on 12/31. 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.
Mon 2/2311:54 pmOGG - ORD
1 stop11h 04mHawaiian Airlines
Mon 3/23:07 pmORD - OGG
1 stop12h 39mHawaiian Airlines
Deal found 12/31$418
This Alaska Airlines deal was found by Cheapflights users on 12/30. 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 1/2211:59 pmOGG - ORD
1 stop10h 30mAlaska Airlines
Sun 1/259:00 amORD - OGG
1 stop33h 36mAlaska Airlines
Deal found 12/30$441
This Alaska Airlines deal was found by Cheapflights users on 12/31. 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 1/2211:59 pmOGG - ORD
1 stop19h 38mMultiple Airlines
Sun 1/253:35 pmORD - OGG
2 stops25h 52mMultiple Airlines
Deal found 12/31$477
This Alaska Airlines deal was found by Cheapflights users on 12/31. 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 2/2311:54 pmOGG - ORD
1 stop11h 04mAlaska Airlines
Mon 3/27:00 amORD - OGG
2 stops20h 46mAlaska Airlines
Deal found 12/31$463
This Delta deal was found by Cheapflights users on 1/2. 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 1/2710:00 pmOGG - MDW
2 stops15h 29mDelta
Thu 2/56:00 amMDW - OGG
1 stop13h 37mDelta
Deal found 1/2$487
This Delta deal was found by Cheapflights users on 12/31. 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 1/2010:00 pmOGG - MDW
2 stops16h 36mDelta
Mon 1/266:00 amMDW - OGG
1 stop13h 37mDelta
Deal found 12/31$487
This Alaska Airlines deal was found by Cheapflights users on 12/31. 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 1/1911:59 pmOGG - ORD
1 stop10h 30mAlaska Airlines
Mon 1/269:00 amORD - OGG
1 stop33h 36mAlaska Airlines
Deal found 12/31$495
This Delta deal was found by Cheapflights users on 12/31. 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 1/199:05 pmOGG - MDW
2 stops17h 31mDelta
Mon 1/266:00 amMDW - OGG
1 stop13h 37mDelta
Deal found 12/31$504
This Delta deal was found by Cheapflights users on 12/31. 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 1/199:05 pmOGG - ORD
2 stops16h 50mDelta
Mon 1/265:30 amORD - OGG
2 stops17h 45mDelta
Deal found 12/31$509
This Delta deal was found by Cheapflights users on 1/2. 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 1/2710:00 pmOGG - ORD
2 stops17h 21mDelta
Thu 2/57:30 amORD - OGG
2 stops15h 45mDelta
Deal found 1/2$549
This Delta deal was found by Cheapflights users on 12/31. 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 1/1410:00 pmOGG - MDW
2 stops16h 32mDelta
Wed 1/216:00 amMDW - OGG
2 stops17h 15mDelta
Deal found 12/31$678
This Delta deal was found by Cheapflights users on 12/31. 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 1/155:10 pmOGG - MDW
1 stop13h 17mDelta
Mon 1/196:00 amMDW - OGG
1 stop13h 37mDelta
Deal found 12/31$891
This Delta deal was found by Cheapflights users on 1/2. 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 1/175:10 pmOGG - MDW
1 stop13h 17mDelta
Wed 1/216:00 amMDW - OGG
2 stops17h 15mDelta
Deal found 1/2$923

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 January 2, 2026.

Round-trip from

$406
(Delta)

One-way from

$191
(Alaska Airlines)

Good round-trip deal

$485 or less

Good one-way deal

$239 or less
From Maui to Chicago (CHI)
Search Deals
One-way flight from Maui to Chicago (CHI)
Search Deals
Price to beat on a round-trip flight from Maui to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Maui to Chicago (CHI).
Search Deals

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 2, 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

Tue 1/20

9:05 pm-1:38 pm

1 stop12h 33m

Chicago O'Hare Intl

Mon 1/26

5:30 am-7:15 pm

2 stops17h 45m

$411

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Mon 2/23

11:54 pm-2:58 pm

1 stop11h 04m

Chicago O'Hare Intl

Mon 3/2

3:07 pm-11:46 pm

1 stop12h 39m

$418

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Thu 1/22

11:59 pm-2:29 pm

1 stop10h 30m

Chicago O'Hare Intl

Sun 1/25

9:00 am-2:36 pm

1 stop33h 36m

$441

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Mon 2/23

11:54 pm-2:58 pm

1 stop11h 04m

Chicago O'Hare Intl

Mon 3/2

7:00 am-11:46 pm

2 stops20h 46m

$463

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Thu 1/22

11:59 pm-11:37 pm

1 stop19h 38m

Chicago O'Hare Intl

Sun 1/25

3:35 pm-1:27 pm

2 stops25h 52m

$477

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Tue 1/27

10:00 pm-5:29 pm

2 stops15h 29m

Chicago Midway

Thu 2/5

6:00 am-3:37 pm

1 stop13h 37m

$487

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Tue 1/20

10:00 pm-6:36 pm

2 stops16h 36m

Chicago Midway

Mon 1/26

6:00 am-3:37 pm

1 stop13h 37m

$487

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Mon 1/19

11:59 pm-2:29 pm

1 stop10h 30m

Chicago O'Hare Intl

Mon 1/26

9:00 am-2:36 pm

1 stop33h 36m

$495

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Mon 1/19

9:05 pm-6:36 pm

2 stops17h 31m

Chicago Midway

Mon 1/26

6:00 am-3:37 pm

1 stop13h 37m

$504

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Mon 1/19

9:05 pm-5:55 pm

2 stops16h 50m

Chicago O'Hare Intl

Mon 1/26

5:30 am-7:15 pm

2 stops17h 45m

$509

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/31

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 January 2, 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.

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 Delta, Hawaiian Airlines, or Alaska Airlines 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 $408.

  • 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 January 2, 2026.
AirlineCheapestAverageFlexibilityOn-time
Hawaiian AirlinesCheapest$322Average$715FlexibilityNo cancel feeOn-time85%
American AirlinesCheapest$455Average$733FlexibilityNo cancel feeOn-time71%
Alaska AirlinesCheapest$468Average$637FlexibilityNo cancel feeOn-time75%
United AirlinesCheapest$793Average$1,193FlexibilityNo cancel feeOn-time69%

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