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$188+ 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 4/17. Fares are subject to change and may not be available on all flights or dates of travel.
OGG — CHI
Apr 16 — Apr 231
Thu 4/16
Thu 4/23
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 March 17, 2026.

This Alaska Airlines deal was found by Cheapflights users on 3/14. 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.
Sun 5/310:51 pm
OGG
-
ORD
1 stop33h 22m
Alaska Airlines
Sat 5/93:52 pm
ORD
-
OGG
1 stop34h 00m
Alaska Airlines
Deal found 3/14$502
This Delta deal was found by Cheapflights users on 3/14. 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.
Sun 5/39:15 pm
OGG
-
ORD
1 stop14h 24m
Delta
Sat 5/910:15 am
ORD
-
OGG
2 stops14h 20m
Delta
Deal found 3/14$534
This Delta deal was found by Cheapflights users on 3/17. 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.
Fri 5/18:00 pm
OGG
-
ORD
1 stop10h 51m
Delta
Fri 5/87:12 am
ORD
-
OGG
1 stop15h 36m
Delta
Deal found 3/17$562
This Alaska Airlines deal was found by Cheapflights users on 3/14. 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 4/1612:44 pm
OGG
-
ORD
1 stop25h 18m
Alaska Airlines
Mon 4/207:59 pm
ORD
-
OGG
1 stop31h 03m
Alaska Airlines
Deal found 3/14$576
This Kiwi.com deal was found by Cheapflights users on 3/17. 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.
Tue 9/11:10 pm
OGG
-
ORD
1 stop12h 50m
Multiple Airlines
Wed 9/91:03 pm
ORD
-
OGG
1 stop13h 33m
Multiple Airlines
Deal found 3/17$586
This Kiwi.com deal was found by Cheapflights users on 3/17. 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.
Tue 9/110:59 pm
OGG
-
ORD
1 stop9h 55m
Multiple Airlines
Tue 9/86:00 am
ORD
-
OGG
1 stop12h 25m
Multiple Airlines
Deal found 3/17$587
This Kiwi.com deal was found by Cheapflights users on 3/17. 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 9/36:00 am
OGG
-
ORD
2 stops12h 59m
Multiple Airlines
Wed 9/91:03 pm
ORD
-
OGG
1 stop13h 33m
Multiple Airlines
Deal found 3/17$592
This Southwest deal was found by Cheapflights users on 3/17. 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 9/310:00 am
OGG
-
MDW
1 stop14h 55m
Southwest
Thu 9/107:10 am
MDW
-
OGG
1 stop10h 40m
Southwest
Deal found 3/17$631
This Southwest deal was found by Cheapflights users on 3/17. 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 5/18:25 pm
OGG
-
MDW
1 stop10h 50m
Southwest
Fri 5/86:40 am
MDW
-
OGG
1 stop10h 55m
Southwest
Deal found 3/17$669
This Southwest deal was found by Cheapflights users on 3/17. 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 4/18:25 pm
OGG
-
MDW
1 stop9h 45m
Southwest
Sun 4/57:00 am
MDW
-
OGG
1 stop12h 15m
Southwest
Deal found 3/17$734
This Southwest deal was found by Cheapflights users on 3/13. 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.
Sat 3/2811:15 am
OGG
-
MDW
2 stops12h 45m
Southwest
Wed 4/16:30 am
MDW
-
OGG
2 stops14h 55m
Southwest
Deal found 3/13$770
This Southwest deal was found by Cheapflights users on 3/15. 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.
Sat 3/2111:15 am
OGG
-
MDW
2 stops17h 25m
Southwest
Wed 3/255:55 am
MDW
-
OGG
1 stop13h 20m
Southwest
Deal found 3/15$800

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 March 17, 2026.

Round-trip from

$502
(Alaska Airlines)

One-way from

$188
(Kiwi.com)

Good round-trip deal

$655 or less

Good one-way deal

$302 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 March 17, 2026.
Use the filters below to find and compare flights from Maui to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Sun 5/3

9:15 pm-4:39 pm

1 stop14h 24m

Chicago O'Hare Intl

Sat 5/9

10:15 am-7:35 pm

2 stops14h 20m

$534

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Thu 4/16

12:44 pm-7:02 pm

1 stop25h 18m

Chicago O'Hare Intl

Mon 4/20

7:59 pm-10:02 pm

1 stop31h 03m

$576

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Tue 9/1

7:00 pm-1:54 pm

2 stops13h 54m

Chicago O'Hare Intl

Wed 9/9

6:00 am-1:25 pm

1 stop12h 25m

$594

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Wed 9/2

9:48 am-7:00 am

2 stops16h 12m

Chicago O'Hare Intl

Tue 9/8

2:54 pm-10:01 pm

1 stop12h 07m

$594

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Thu 4/16

12:44 pm-11:59 pm

1 stop30h 15m

Chicago O'Hare Intl

Mon 4/20

7:59 pm-4:31 pm

2 stops25h 32m

$601

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Thu 9/3

10:00 am-5:55 am

1 stop14h 55m

Chicago Midway

Thu 9/10

7:10 am-12:50 pm

1 stop10h 40m

$631
Quickest round-trip

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Fri 5/1

8:25 pm-12:15 pm

1 stop10h 50m

Chicago Midway

Fri 5/8

6:40 am-12:35 pm

1 stop10h 55m

$669

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Wed 4/1

8:25 pm-11:10 am

1 stop9h 45m

Chicago Midway

Sun 4/5

7:00 am-2:15 pm

1 stop12h 15m

$734

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Sat 3/28

11:15 am-5:00 am

2 stops12h 45m

Chicago Midway

Wed 4/1

6:30 am-4:25 pm

2 stops14h 55m

$770

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Fri 3/27

7:00 pm-11:55 am

2 stops11h 55m

Chicago Midway

Tue 3/31

10:00 am-4:25 pm

1 stop11h 25m

$820

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/17

Showing 1-10 of 32 resultsSorted by cheapest first
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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 March 17, 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.

Weekly flight availability from Maui to Chicago

Explore weekly flight availability from Maui to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated March 17, 2026.

The most flights from zzFUK to CHI are scheduled on a Monday (2 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (2 on average).

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 14h 24m. Fly via Delta, Alaska Airlines, 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 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 $265. On average you can expect to pay $564. The most popular route, (Kahului - Chicago O'Hare Intl), can usually be booked for $512.

  • 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

Browse thousands of different options on Cheapflights for your next trip

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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 March 17, 2026.
AirlineCheapestAverageFlexibilityOn-time
Hawaiian AirlinesCheapest$322Average$629FlexibilityNo cancel feeOn-time85%
American AirlinesCheapest$461Average$818FlexibilityNo cancel feeOn-time71%
Alaska AirlinesCheapest$468Average$683FlexibilityNo cancel feeOn-time75%

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