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$186+ 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 3/2. Fares are subject to change and may not be available on all flights or dates of travel.
OGG — CHI
Jan 15 — Jan 221
Thu 1/15
Thu 1/22
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 16, 2025.

This American Airlines deal was found by Cheapflights users on 12/14. 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 12/177:00 pmOGG - ORD
1 stop12h 44mAmerican Airlines
Wed 12/315:15 amORD - OGG
1 stop14h 07mAmerican Airlines
Deal found 12/14$808
This Delta deal was found by Cheapflights users on 12/14. 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 - ORD
2 stops14h 45mDelta
Wed 12/316:45 amORD - OGG
1 stop12h 39mDelta
Deal found 12/14$813
This United Airlines deal was found by Cheapflights users on 12/15. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/215:15 pmOGG - ORD
Nonstop7h 59mUnited Airlines
Thu 1/18:20 pmORD - OGG
2 stops20h 34mUnited Airlines
Deal found 12/15$860
This Alaska Airlines deal was found by Cheapflights users on 12/15. 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 12/186:48 amOGG - ORD
2 stops13h 11mMultiple Airlines
Mon 12/228:39 amORD - OGG
1 stop16h 58mMultiple Airlines
Deal found 12/15$868
This Southwest deal was found by Cheapflights users on 12/15. 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 12/189:35 pmOGG - MDW
1 stop10h 40mSouthwest
Mon 12/227:50 amMDW - OGG
1 stop12h 30mSouthwest
Deal found 12/15$873
This Delta deal was found by Cheapflights users on 12/14. 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 12/256:00 amOGG - ORD
2 stops13h 59mDelta
Wed 12/316:00 amORD - OGG
1 stop16h 18mDelta
Deal found 12/14$918
This Delta deal was found by Cheapflights users on 12/15. 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.
Sun 12/2111:40 pmOGG - ORD
2 stops17h 54mDelta
Thu 1/17:25 amORD - OGG
2 stops18h 14mDelta
Deal found 12/15$949
This American Airlines deal was found by Cheapflights users on 12/14. 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.
Thu 12/2511:11 pmOGG - ORD
1 stop11h 13mAmerican Airlines
Wed 12/315:15 amORD - OGG
1 stop14h 07mAmerican Airlines
Deal found 12/14$958
This Alaska Airlines deal was found by Cheapflights users on 12/15. 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 12/1811:59 pmOGG - ORD
1 stop10h 38mAlaska Airlines
Mon 12/228:39 amORD - OGG
1 stop16h 58mAlaska Airlines
Deal found 12/15$1,016
This United Airlines deal was found by Cheapflights users on 12/14. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/258:00 amOGG - ORD
1 stop17h 27mUnited Airlines
Wed 12/319:20 amORD - OGG
Nonstop9h 24mUnited Airlines
Deal found 12/14$1,023
This Delta deal was found by Cheapflights users on 12/15. 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 12/1811:15 pmOGG - MDW
2 stops15h 03mDelta
Mon 12/229:29 amMDW - OGG
2 stops13h 57mDelta
Deal found 12/15$1,406

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 16, 2025.

Round-trip from

$421
(American Airlines)

One-way from

$186
(Kiwi.com)

Good round-trip deal

$554 or less

Good one-way deal

$292 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 December 16, 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-11:37 pm

1 stop19h 38m

Chicago O'Hare Intl

Mon 1/19

9:00 am-10:59 pm

1 stop17h 59m

$381

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Thu 2/19

11:54 pm-2:58 pm

1 stop11h 04m

Chicago O'Hare Intl

Wed 3/4

8:20 am-10:21 pm

2 stops18h 01m

$439

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Thu 1/15

11:59 pm-2:29 pm

1 stop10h 30m

Chicago O'Hare Intl

Mon 1/19

6:06 pm-3:35 pm

2 stops25h 29m

$487

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Thu 2/19

1:53 pm-8:40 am

2 stops14h 47m

Chicago O'Hare Intl

Wed 3/4

7:40 am-7:15 pm

2 stops15h 35m

$495

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Sat 2/28

11:54 pm-2:58 pm

1 stop11h 04m

Chicago O'Hare Intl

Sun 3/8

8:20 am-10:46 pm

1 stop19h 26m

$535

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

$541

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Thu 2/19

1:53 pm-9:06 am

2 stops15h 13m

Chicago Midway

Wed 3/4

6:00 am-8:26 pm

2 stops18h 26m

$657

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Sat 2/28

12:45 pm-5:05 am

2 stops12h 20m

Chicago Midway

Sun 3/8

7:10 am-4:35 pm

2 stops14h 25m

$695

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Thu 1/15

2:25 pm-6:46 pm

2 stops24h 21m

Chicago O'Hare Intl

Mon 1/19

8:02 pm-12:57 pm

2 stops20h 55m

$782

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Sat 2/28

5:10 pm-9:56 am

1 stop12h 46m

Chicago Midway

Sun 3/8

10:49 am-6:40 pm

1 stop12h 51m

$892

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/13

Showing 1-10 of 29 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 16, 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, Delta, 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 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 $519.

  • 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 December 16, 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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