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$231+ 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 9/10. Fares are subject to change and may not be available on all flights or dates of travel.
OGG — CHI
jul. 5 — jul. 121
sáb. 7/5
sáb. 7/12
1 adult, Economy
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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 junio 30, 2025.

Round-trip from

$533
(Alaska Airlines)

One-way from

$231
(American Airlines)

Good one-way deal

$653 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 one-way flight from Maui to Chicago (CHI).
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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 junio 30, 2025.

This Alaska Airlines deal was found by Cheapflights users on 6/29. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 10/28:00 amOGG - ORD
1 stop11h 03mAlaska Airlines
jue. 10/98:20 amORD - OGG
2 stops15h 22mAlaska Airlines
Deal found 6/29$511
This Delta deal was found by Cheapflights users on 6/29. 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.
sáb. 10/49:07 pmOGG - ORD
1 stop15h 08mDelta
dom. 10/127:30 amORD - OGG
1 stop15h 16mDelta
Deal found 6/29$553
This Southwest deal was found by Cheapflights users on 6/29. 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.
vie. 10/38:30 pmOGG - MDW
1 stop10h 30mSouthwest
sáb. 10/115:00 amMDW - OGG
1 stop13h 15mSouthwest
Deal found 6/29$638
This Delta deal was found by Cheapflights users on 6/28. 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.
dom. 7/138:58 pmOGG - MDW
2 stops15h 41mDelta
jue. 7/179:25 amMDW - OGG
2 stops15h 08mDelta
Deal found 6/28$1,211

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 junio 30, 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

mié. 8/13

9:00 pm-4:59 pm

2 stops14h 59m

Chicago O'Hare Intl

dom. 8/17

7:00 am-8:39 pm

1 stop18h 39m

$533

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

vie. 10/3

8:30 pm-12:00 pm

1 stop10h 30m

Chicago Midway

sáb. 10/11

5:00 am-1:15 pm

1 stop13h 15m

$638

KahuluiChicago

OGG - ORD

OGGORD

Kahului

jue. 7/17

8:45 pm-3:20 pm

1 stop13h 35m

Chicago O'Hare Intl

lun. 7/21

6:15 am-4:30 pm

2 stops15h 15m

$813

KahuluiChicago

OGG - ORD

OGGORD

Kahului

mié. 7/16

2:40 pm-11:52 am

1 stop16h 12m

Chicago O'Hare Intl

lun. 7/21

4:50 pm-1:19 pm

1 stop25h 29m

$854

KahuluiChicago

OGG - ORD

OGGORD

Kahului

mié. 7/16

11:15 am-5:40 am

1 stop13h 25m

Chicago O'Hare Intl

sáb. 7/26

6:00 am-1:40 pm

1 stop12h 40m

$874

KahuluiChicago

OGG - ORD

OGGORD

Kahului

jue. 7/17

10:18 pm-7:14 pm

1 stop15h 56m

Chicago O'Hare Intl

lun. 7/21

6:13 am-8:48 pm

1 stop19h 35m

$881

KahuluiChicago

OGG - ORD

OGGORD

Kahului

lun. 7/28

10:15 am-10:16 am

2 stops19h 01m

Chicago O'Hare Intl

lun. 8/4

6:15 pm-7:33 pm

2 stops30h 18m

$898

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

sáb. 10/4

12:15 pm-8:53 am

2 stops15h 38m

Chicago Midway

dom. 10/12

6:00 am-6:49 pm

2 stops17h 49m

$1,018

KahuluiChicago

OGG - ORD

OGGORD

Kahului

mié. 9/10

1:14 pm-6:01 am

1 stop11h 47m

$231

KahuluiChicago

OGG - ORD

OGGORD

Kahului

vie. 9/12

8:00 am-12:03 am

1 stop11h 03m

$234

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/30

Showing 1-10 of 17 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, August is the cheapest month in which you can book a flight from Maui to Chicago (average of $245). Flying from Maui to Chicago in March is currently the most expensive (average of $321). 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 junio 30, 2025.

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.

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated junio 30, 2025.
Peruse reviews from past customers who have flown with Alaska Airlines, Southwest, and Delta from Maui to Chicago to help guide your decision. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Entertainment

7.1

Overall

8.0

Boarding

8.1

Crew

8.5

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Entertainment

7.1

Overall

8.0

Boarding

8.1

Crew

8.5

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Southwest
8.0
Very good
4,278 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Entertainment

7.1

Overall

8.0

Boarding

8.1

Crew

8.5

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Delta
8.0
Very good
7,969 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Entertainment

7.1

Overall

8.0

Boarding

8.1

Crew

8.5

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Hawaiian Airlines
7.8
Good
2,533 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Entertainment

7.1

Overall

8.0

Boarding

8.1

Crew

8.5

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Qatar Airways
7.4
Good
3,596 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Entertainment

7.1

Overall

8.0

Boarding

8.1

Crew

8.5

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

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.

  • What are the cheapest airlines to fly from Maui to Chicago one-way?

    For one-way options, check prices for American Airlines. According to our data, you can fly for as low as $231. Users have also found prices from $234 and $236 on Alaska Airlines and Delta, respectively.

  • What are the cheapest flights from Maui to Chicago?

    The cheapest flight price from Maui to Chicago is $561. On average you can expect to pay $812. The most popular route, (Kahului - Chicago O'Hare Intl), can usually be booked for $517.

  • 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, August is the cheapest month in which you can book a flight from Maui to Chicago (average of $245). Flying from Maui to Chicago in March is currently the most expensive (average of $321). 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 Maui?

Book flights to Maui if you plan to visit one of these locations
Merrillville
Lansing
Benton Harbor
Porter
Hammond
Valparaiso
Chesterton

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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 junio 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
Hawaiian AirlinesCheapest$322Average$715FlexibilityNo cancel feeOn-time85%
American AirlinesCheapest$349Average$501FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$478Average$827FlexibilityNo cancel feeOn-time69%
Alaska AirlinesCheapest$508Average$715FlexibilityNo cancel feeOn-time75%

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