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$202+ 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 4/16. Fares are subject to change and may not be available on all flights or dates of travel.
OGG — CHI
Feb 19 — Feb 261
Thu 2/19
Thu 2/26
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 January 20, 2026.

This Expedia deal was found by Cheapflights users on 1/18. 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.
Tue 3/311:54 pm
OGG
-
ORD
1 stop20h 05m
Alaska Airlines
Mon 3/98:20 am
ORD
-
OGG
1 stop19h 26m
Alaska Airlines
Deal found 1/18$393
This Alaska Airlines deal was found by Cheapflights users on 1/18. 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 3/311:54 pm
OGG
-
ORD
1 stop20h 05m
Multiple Airlines
Mon 3/98:20 am
ORD
-
OGG
2 stops26h 56m
Multiple Airlines
Deal found 1/18$398
This Kiwi.com deal was found by Cheapflights users on 1/19. 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.
Wed 3/253:10 pm
OGG
-
ORD
1 stop32h 39m
Multiple Airlines
Mon 4/67:45 pm
ORD
-
OGG
2 stops39h 31m
Multiple Airlines
Deal found 1/19$462
This American Airlines deal was found by Cheapflights users on 1/19. 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 4/69:45 am
ORD
-
OGG
1 stop13h 38m
American Airlines
Deal found 1/19$468
This Expedia deal was found by Cheapflights users on 1/19. 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.
Mon 3/3011:02 pm
OGG
-
ORD
1 stop10h 19m
Alaska Airlines
Mon 4/138:20 am
ORD
-
OGG
1 stop18h 42m
Alaska Airlines
Deal found 1/19$497
This Expedia deal was found by Cheapflights users on 1/19. 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.
Mon 3/3011:02 pm
OGG
-
ORD
1 stop10h 19m
Multiple Airlines
Mon 4/138:20 am
ORD
-
OGG
2 stops17h 05m
Multiple Airlines
Deal found 1/19$516
This Southwest deal was found by Cheapflights users on 1/18. 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.
Tue 3/39:25 pm
OGG
-
MDW
1 stop11h 35m
Southwest
Mon 3/96:05 am
MDW
-
OGG
1 stop11h 30m
Southwest
Deal found 1/18$532
This Delta deal was found by Cheapflights users on 1/20. 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 3/114:00 pm
OGG
-
ORD
1 stop11h 30m
Delta
Mon 3/167:10 am
ORD
-
OGG
2 stops16h 15m
Delta
Deal found 1/20$532
This Southwest deal was found by Cheapflights users on 1/19. 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 2/69:25 pm
OGG
-
MDW
1 stop10h 30m
Southwest
Mon 2/98:10 am
MDW
-
OGG
1 stop12h 15m
Southwest
Deal found 1/19$568
This Alaska Airlines deal was found by Cheapflights users on 1/19. 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.
Fri 2/611:00 pm
OGG
-
ORD
1 stop11h 38m
Alaska Airlines
Mon 2/99:00 am
ORD
-
OGG
1 stop17h 59m
Alaska Airlines
Deal found 1/19$568
This Southwest deal was found by Cheapflights users on 1/19. 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 3/2510:00 am
OGG
-
MDW
1 stop14h 55m
Southwest
Mon 4/65:00 am
MDW
-
OGG
1 stop12h 30m
Southwest
Deal found 1/19$571
This Alaska Airlines deal was found by Cheapflights users on 1/19. 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.
Fri 2/611:00 pm
OGG
-
ORD
1 stop11h 38m
Multiple Airlines
Mon 2/99:00 am
ORD
-
OGG
2 stops25h 17m
Multiple Airlines
Deal found 1/19$573

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 20, 2026.

Round-trip from

$393
(Expedia)

One-way from

$202
(Alaska Airlines)

Good round-trip deal

$419 or less

Good one-way deal

$299 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 20, 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 3/3

11:54 pm-11:59 pm

1 stop20h 05m

Chicago O'Hare Intl

Mon 3/9

8:20 am-6:16 am

2 stops26h 56m

$398

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Wed 3/25

3:10 pm-4:49 am

1 stop32h 39m

Chicago O'Hare Intl

Mon 4/6

7:45 pm-6:16 am

2 stops39h 31m

$462

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Wed 3/25

1:46 pm-7:25 am

1 stop12h 39m

Chicago O'Hare Intl

Mon 4/6

9:45 am-6:23 pm

1 stop13h 38m

$468

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Tue 3/3

9:25 pm-1:00 pm

1 stop11h 35m

Chicago Midway

Mon 3/9

6:05 am-12:35 pm

1 stop11h 30m

$532

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Wed 3/11

4:00 pm-8:30 am

1 stop11h 30m

Chicago O'Hare Intl

Mon 3/16

7:10 am-6:25 pm

2 stops16h 15m

$532

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Fri 2/6

11:00 pm-2:38 pm

1 stop11h 38m

Chicago O'Hare Intl

Mon 2/9

9:00 am-10:59 pm

1 stop17h 59m

$568

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Fri 2/6

9:25 pm-11:55 am

1 stop10h 30m

Chicago Midway

Mon 2/9

8:10 am-4:25 pm

1 stop12h 15m

$568

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Fri 2/6

6:00 am-11:50 pm

2 stops13h 50m

Chicago O'Hare Intl

Mon 2/9

9:00 am-8:30 pm

2 stops15h 30m

$579

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Wed 3/25

12:59 pm-8:53 am

2 stops14h 54m

Chicago Midway

Mon 4/6

6:00 am-3:13 pm

1 stop14h 13m

$592

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Wed 3/25

8:25 pm-3:05 pm

2 stops13h 40m

Chicago O'Hare Intl

Mon 4/6

6:15 am-4:35 pm

2 stops15h 20m

$632

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/18

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 20, 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 11h 30m. Fly via American Airlines, Southwest, or Delta 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 $201. On average you can expect to pay $748. The most popular route, (Kahului - Chicago O'Hare Intl), can usually be booked for $398.

  • 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 20, 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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