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$192+ 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 1/12. Fares are subject to change and may not be available on all flights or dates of travel.
OGG — CHI
Dec 13 — Dec 201
Sat 12/13
Sat 12/20
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 November 13, 2025.

This American Airlines deal was found by Cheapflights users on 11/12. 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 11/263:01 pmOGG - ORD
1 stop10h 55mAmerican Airlines
Thu 11/277:29 amORD - OGG
1 stop12h 01mAmerican Airlines
Deal found 11/12$599
This Delta deal was found by Cheapflights users on 11/13. 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.
Thu 12/188:59 pmOGG - ORD
1 stop11h 41mDelta
Mon 12/227:25 amORD - OGG
2 stops18h 14mDelta
Deal found 11/13$704
This Southwest deal was found by Cheapflights users on 11/10. 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 11/269:25 pmOGG - MDW
1 stop16h 30mSouthwest
Sun 11/305:35 amMDW - OGG
1 stop11h 50mSouthwest
Deal found 11/10$713
This Cheapflightsfares deal was found by Cheapflights users on 11/13. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/1411:59 pmOGG - ORD
1 stop9h 55mAlaska Airlines
Sun 11/166:00 amORD - OGG
1 stop12h 12mAlaska Airlines
Deal found 11/13$762
This Southwest deal was found by Cheapflights users on 11/10. 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 11/278:55 pmOGG - MDW
1 stop11h 35mSouthwest
Sun 11/3010:55 pmMDW - OGG
1 stop17h 30mSouthwest
Deal found 11/10$768
This Southwest deal was found by Cheapflights users on 11/13. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/149:25 pmOGG - ORD
1 stop12h 05mSouthwest
Mon 11/177:15 amORD - OGG
2 stops13h 20mSouthwest
Deal found 11/13$768
This Alaska Airlines deal was found by Cheapflights users on 11/13. 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.
Thu 12/183:52 pmOGG - ORD
1 stop24h 10mAlaska Airlines
Mon 12/228:58 pmORD - OGG
1 stop28h 39mAlaska Airlines
Deal found 11/13$773
This Kiwi.com deal was found by Cheapflights users on 11/13. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/284:03 pmOGG - ORD
1 stop28h 56mMultiple Airlines
Tue 12/24:58 pmORD - OGG
2 stops47h 21mMultiple Airlines
Deal found 11/13$808
This Alaska Airlines deal was found by Cheapflights users on 11/12. 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 11/2610:48 amOGG - ORD
2 stops15h 40mAlaska Airlines
Thu 11/278:20 amORD - OGG
1 stop35h 20mAlaska Airlines
Deal found 11/12$839
This Delta deal was found by Cheapflights users on 11/11. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/205:10 pmOGG - MDW
1 stop12h 42mDelta
Wed 11/266:00 amMDW - OGG
2 stops16h 56mDelta
Deal found 11/11$1,252

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 November 13, 2025.

Round-trip from

$423
(Alaska Airlines)

One-way from

$192
(Alaska Airlines)

Good round-trip deal

$350 or less

Good one-way deal

$371 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 November 13, 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 12/9

4:04 pm-6:05 am

1 stop34h 01m

Chicago O'Hare Intl

Sat 12/13

9:06 pm-12:19 pm

1 stop19h 13m

$413

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Tue 3/3

6:48 am-11:59 pm

2 stops13h 11m

Chicago O'Hare Intl

Wed 3/4

8:20 am-11:46 pm

1 stop19h 26m

$423

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Tue 3/10

6:01 am-11:59 pm

2 stops12h 58m

Chicago O'Hare Intl

Wed 3/11

8:20 am-10:46 pm

1 stop19h 26m

$442

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Wed 11/26

3:01 pm-5:56 am

1 stop10h 55m

Chicago O'Hare Intl

Thu 11/27

7:29 am-3:30 pm

1 stop12h 01m

$574

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Tue 4/28

12:45 pm-6:05 pm

2 stops24h 20m

Chicago Midway

Thu 4/30

1:00 pm-11:01 am

2 stops27h 01m

$670

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Wed 11/26

9:25 pm-5:55 pm

1 stop16h 30m

Chicago Midway

Sun 11/30

5:35 am-1:25 pm

1 stop11h 50m

$713

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Thu 11/27

9:45 pm-4:35 pm

2 stops14h 50m

Chicago Midway

Sun 11/30

5:35 am-1:25 pm

1 stop11h 50m

$718

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Thu 12/4

4:04 pm-12:13 am

1 stop28h 09m

$192

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Mon 1/12

11:59 pm-11:37 pm

1 stop19h 38m

$192

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Thu 12/18

11:59 pm-8:02 pm

1 stop16h 03m

$202

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/12

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 $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 November 13, 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 13h 11m. 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 Alaska Airlines. According to our data, you can fly for as low as $192. Users have also found prices from $227 and $236 on Delta and Southwest, 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 $679. The most popular route, (Kahului - Chicago O'Hare Intl), can usually be booked for $404.

  • 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
Hammond
Porter
Benton Harbor
Merrillville

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 November 13, 2025.
AirlineCheapestAverageFlexibilityOn-time
Hawaiian AirlinesCheapest$322Average$715FlexibilityNo cancel feeOn-time85%
United AirlinesCheapest$432Average$902FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$455Average$729FlexibilityNo cancel feeOn-time71%
Alaska AirlinesCheapest$468Average$635FlexibilityNo cancel feeOn-time75%

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