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$200+ 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 1/15. Fares are subject to change and may not be available on all flights or dates of travel.
OGG — CHI
Nov 13 — Nov 201
Thu 11/13
Thu 11/20
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 October 14, 2025.

This Delta deal was found by Cheapflights users on 10/14. 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.
Tue 11/410:09 pmOGG - ORD
1 stop11h 21mDelta
Thu 11/137:47 amORD - OGG
1 stop16h 20mDelta
Deal found 10/14$424
This Kiwi.com deal was found by Cheapflights users on 10/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/304:29 pmOGG - ORD
2 stops25h 31mMultiple Airlines
Mon 11/39:22 pmORD - OGG
1 stop20h 18mMultiple Airlines
Deal found 10/14$479
This Southwest deal was found by Cheapflights users on 10/12. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/2212:45 pmOGG - MDW
2 stops12h 20mSouthwest
Sat 11/296:05 amMDW - OGG
1 stop11h 15mSouthwest
Deal found 10/12$557
This Alaska Airlines deal was found by Cheapflights users on 10/13. 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 12/111:50 pmOGG - ORD
1 stop20h 00mAlaska Airlines
Sun 12/78:59 pmORD - OGG
1 stop30h 41mAlaska Airlines
Deal found 10/13$634
This Alaska Airlines deal was found by Cheapflights users on 10/13. 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.
Tue 10/2810:59 pmOGG - ORD
1 stop20h 00mAlaska Airlines
Sat 11/18:59 pmORD - OGG
1 stop30h 51mAlaska Airlines
Deal found 10/13$712
This Alaska Airlines deal was found by Cheapflights users on 10/14. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/306:00 amOGG - ORD
2 stops13h 24mAlaska Airlines
Mon 11/38:00 amORD - OGG
2 stops16h 25mAlaska Airlines
Deal found 10/14$724
This Delta deal was found by Cheapflights users on 10/13. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/15:10 pmOGG - ORD
2 stops16h 40mDelta
Sun 12/76:45 amORD - OGG
2 stops17h 33mDelta
Deal found 10/13$749
This Delta deal was found by Cheapflights users on 10/13. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/2812:35 pmOGG - ORD
2 stops18h 42mDelta
Sat 11/17:10 amORD - OGG
2 stops16h 33mDelta
Deal found 10/13$894
This Delta deal was found by Cheapflights users on 10/12. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/278:15 pmOGG - MDW
2 stops17h 10mDelta
Fri 10/319:35 amMDW - OGG
2 stops13h 43mDelta
Deal found 10/12$897

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 October 14, 2025.

Round-trip from

$422
(Alaska Airlines)

One-way from

$200
(Kissandfly.com)

Good round-trip deal

$710 or less

Good one-way deal

$359 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 October 14, 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 3/3

9:48 am-5:04 am

2 stops15h 16m

Chicago O'Hare Intl

Wed 3/4

9:00 am-10:48 pm

1 stop17h 48m

$422

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Tue 11/4

10:09 pm-1:30 pm

1 stop11h 21m

Chicago O'Hare Intl

Thu 11/13

7:47 am-8:07 pm

1 stop16h 20m

$424

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Thu 10/30

4:29 pm-11:00 pm

2 stops25h 31m

Chicago O'Hare Intl

Mon 11/3

9:22 pm-1:40 pm

1 stop20h 18m

$479

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Sat 11/22

12:45 pm-5:05 am

2 stops12h 20m

Chicago Midway

Sat 11/29

6:05 am-1:20 pm

1 stop11h 15m

$557

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Mon 12/1

11:50 pm-11:50 pm

1 stop20h 00m

Chicago O'Hare Intl

Sun 12/7

8:59 pm-11:40 pm

1 stop30h 41m

$634

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Mon 10/27

8:15 pm-6:25 pm

2 stops17h 10m

Chicago Midway

Fri 10/31

9:35 am-6:18 pm

2 stops13h 43m

$897

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Thu 1/15

11:59 pm-2:29 pm

1 stop10h 30m

$200

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Thu 1/15

11:59 pm-2:29 pm

1 stop10h 30m

$202

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Mon 11/24

11:50 pm-11:32 pm

1 stop19h 42m

$212

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Mon 1/12

11:59 pm-11:37 pm

1 stop19h 38m

$213

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/14

Showing 1-10 of 21 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 $212). 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 October 14, 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 21m. Fly via Alaska Airlines, Delta, 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 Hawaiian Airlines. According to our data, you can fly for as low as $200. Users have also found prices from $202 and $231 on Alaska Airlines 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 $839. The most popular route, (Kahului - Chicago O'Hare Intl), can usually be booked for $436.

  • 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 $212). 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
Merrillville
Lansing
Hammond
Porter
Benton Harbor
Chesterton

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 October 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
Hawaiian AirlinesCheapest$322Average$715FlexibilityNo cancel feeOn-time85%
American AirlinesCheapest$429Average$729FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$432Average$902FlexibilityNo cancel feeOn-time69%
Alaska AirlinesCheapest$468Average$637FlexibilityNo cancel feeOn-time75%

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