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$234+ 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 5/26. Fares are subject to change and may not be available on all flights or dates of travel.
OGG — CHI
Jun 1 — Jun 81
Mon 6/1
Mon 6/8
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 May 2, 2026.

This CheapOair deal was found by Cheapflights users on 4/27. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/218:00 am
OGG
-
ORD
1 stop10h 59m
Alaska Airlines
Wed 5/277:40 am
ORD
-
OGG
1 stop13h 10m
Alaska Airlines
Deal found 4/27$510
This Delta deal was found by Cheapflights users on 4/27. 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 5/2110:00 pm
OGG
-
ORD
2 stops15h 05m
Delta
Wed 5/277:00 am
ORD
-
OGG
2 stops17h 35m
Delta
Deal found 4/27$541
This Alaska Airlines deal was found by Cheapflights users on 4/28. 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 6/210:30 pm
OGG
-
ORD
1 stop15h 20m
Alaska Airlines
Mon 6/87:59 pm
ORD
-
OGG
1 stop30h 31m
Alaska Airlines
Deal found 4/28$551
This American Airlines deal was found by Cheapflights users on 4/30. 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 5/215:45 pm
OGG
-
ORD
1 stop13h 27m
American Airlines
Wed 5/273:20 pm
ORD
-
OGG
1 stop11h 02m
American Airlines
Deal found 4/30$577
This CheapOair deal was found by Cheapflights users on 4/27. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/218:00 am
OGG
-
ORD
1 stop10h 59m
Multiple Airlines
Wed 5/277:40 am
ORD
-
OGG
2 stops17h 33m
Multiple Airlines
Deal found 4/27$581
This Alaska Airlines deal was found by Cheapflights users on 4/30. 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 8/312:34 pm
OGG
-
ORD
1 stop10h 48m
Alaska Airlines
Tue 9/12:18 pm
ORD
-
OGG
1 stop12h 20m
Alaska Airlines
Deal found 4/30$584
This Alaska Airlines deal was found by Cheapflights users on 4/30. 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 8/319:15 am
OGG
-
ORD
2 stops16h 07m
Multiple Airlines
Tue 9/12:18 pm
ORD
-
OGG
1 stop12h 20m
Multiple Airlines
Deal found 4/30$590
This Southwest deal was found by Cheapflights users on 4/29. 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 5/78:55 pm
OGG
-
MDW
1 stop11h 10m
Southwest
Tue 5/126:45 am
MDW
-
OGG
1 stop10h 50m
Southwest
Deal found 4/29$644
This Delta deal was found by Cheapflights users on 4/29. 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 6/119:50 pm
OGG
-
MDW
2 stops15h 41m
Delta
Thu 6/189:17 am
MDW
-
OGG
2 stops15h 12m
Delta
Deal found 4/29$816
This Southwest deal was found by Cheapflights users on 5/1. 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 5/168:25 pm
OGG
-
MDW
1 stop10h 00m
Southwest
Wed 5/206:10 am
MDW
-
OGG
1 stop12h 00m
Southwest
Deal found 5/1$820
This Delta deal was found by Cheapflights users on 4/28. 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 7/1910:00 pm
OGG
-
MDW
2 stops15h 18m
Delta
Thu 7/309:19 am
MDW
-
OGG
2 stops15h 15m
Delta
Deal found 4/28$852
This Southwest deal was found by Cheapflights users on 4/28. 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.
Sun 7/198:55 pm
OGG
-
MDW
1 stop10h 35m
Southwest
Thu 7/305:20 am
MDW
-
OGG
1 stop12h 20m
Southwest
Deal found 4/28$855

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 May 2, 2026.

Round-trip from

$510
(CheapOair)

One-way from

$234
(WAYA)

Good one-way deal

$467 or less
From Maui to Chicago (CHI)
Search Deals
One-way 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 May 2, 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

Thu 5/21

10:00 pm-6:05 pm

2 stops15h 05m

Chicago O'Hare Intl

Wed 5/27

7:00 am-7:35 pm

2 stops17h 35m

$541

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Mon 8/31

2:34 pm-6:22 am

1 stop10h 48m

Chicago O'Hare Intl

Tue 9/1

2:18 pm-9:38 pm

1 stop12h 20m

$584

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Mon 8/31

10:51 am-6:22 am

2 stops14h 31m

Chicago O'Hare Intl

Tue 9/1

9:00 am-6:24 pm

2 stops14h 24m

$604
Quickest round-trip

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Wed 7/1

2:38 pm-5:46 am

1 stop10h 08m

Chicago O'Hare Intl

Tue 7/7

6:00 am-11:46 am

1 stop10h 46m

$674

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Sat 5/16

2:05 pm-5:40 am

1 stop10h 35m

Chicago O'Hare Intl

Wed 5/20

6:20 am-12:43 pm

1 stop11h 23m

$674

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Fri 5/15

8:48 pm-4:56 pm

2 stops15h 08m

Chicago O'Hare Intl

Tue 5/19

2:10 pm-9:30 pm

1 stop12h 20m

$680

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Thu 6/11

9:50 pm-6:29 pm

2 stops15h 39m

Chicago O'Hare Intl

Thu 6/18

6:30 am-7:29 pm

2 stops17h 59m

$685

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Thu 6/11

9:50 pm-6:31 pm

2 stops15h 41m

Chicago Midway

Thu 6/18

9:17 am-7:29 pm

2 stops15h 12m

$816

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Sat 5/16

8:25 pm-11:25 am

1 stop10h 00m

Chicago Midway

Wed 5/20

6:10 am-1:10 pm

1 stop12h 00m

$820

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Sun 7/19

8:55 pm-12:30 pm

1 stop10h 35m

Chicago Midway

Thu 7/30

5:45 am-2:50 pm

2 stops14h 05m

$861

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/1

Showing 1-10 of 33 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 May 2, 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 10h. Fly via Delta, Alaska Airlines, 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 $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 $335. On average you can expect to pay $488. The most popular route, (Kahului - Chicago O'Hare Intl), can usually be booked for $577.

  • 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
Benton Harbor
Lansing
Merrillville
Hammond
Porter

Browse thousands of different options on Cheapflights for your next trip

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Top 2 airlines flying from Maui to Chicago

Discover the top 2 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 May 2, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$461Average$729FlexibilityNo cancel feeOn-time71%
Alaska AirlinesCheapest$465Average$683FlexibilityNo cancel feeOn-time75%

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