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$254+ 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 5/19. Fares are subject to change and may not be available on all flights or dates of travel.
OGG — CHI
Apr 29 — May 61
Tue 4/29
Tue 5/6
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 April 24, 2025.

Round-trip from

$540
(Alaska Airlines)

One-way from

$254
(Delta)

Good round-trip deal

$700 or less

Good one-way deal

$395 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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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 April 24, 2025.

This Alaska Airlines deal was found by Cheapflights users on 4/21. 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 5/299:46 pmOGG - ORD
1 stop21h 10mAlaska Airlines
Tue 6/37:51 pmORD - OGG
1 stop31h 22mAlaska Airlines
Deal found 4/21$522
This Delta deal was found by Cheapflights users on 4/22. 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.
Mon 6/29:30 pmOGG - ORD
1 stop11h 00mDelta
Tue 6/108:29 amORD - OGG
2 stops15h 59mDelta
Deal found 4/22$594
This Hawaiian Airlines deal was found by Cheapflights users on 4/23. 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 Hawaiian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/411:15 amOGG - ORD
1 stop13h 25mHawaiian Airlines
Mon 8/116:00 amORD - OGG
1 stop14h 10mHawaiian Airlines
Deal found 4/23$615
This United Airlines deal was found by Cheapflights users on 4/23. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/37:00 amOGG - ORD
1 stop17h 18mUnited Airlines
Wed 8/136:30 amORD - OGG
1 stop14h 52mUnited Airlines
Deal found 4/23$664
This Southwest deal was found by Cheapflights users on 4/23. 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.
Mon 8/48:30 pmOGG - MDW
1 stop12h 25mSouthwest
Mon 8/115:35 amMDW - OGG
1 stop12h 25mSouthwest
Deal found 4/23$763
This Delta deal was found by Cheapflights users on 4/22. 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 5/78:50 pmOGG - MDW
2 stops15h 55mDelta
Sun 5/116:00 amMDW - OGG
2 stops18h 25mDelta
Deal found 4/22$846
This Southwest deal was found by Cheapflights users on 4/23. 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 7/198:45 pmOGG - ORD
2 stops12h 20mSouthwest
Wed 7/237:00 amORD - OGG
2 stops15h 05mSouthwest
Deal found 4/23$984
This United deal was found by Cheapflights users on 4/23. 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 United is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/195:10 pmOGG - ORD
Nonstop7h 55mMultiple Airlines
Wed 7/236:00 amORD - OGG
1 stop14h 10mMultiple Airlines
Deal found 4/23$1,050

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 April 24, 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

Thu 5/29

9:46 pm-11:56 pm

1 stop21h 10m

Chicago O'Hare Intl

Tue 6/3

7:51 pm-10:13 pm

1 stop31h 22m

$522

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Mon 6/2

9:30 pm-1:30 pm

1 stop11h 00m

Chicago O'Hare Intl

Tue 6/10

8:29 am-7:28 pm

2 stops15h 59m

$594

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Tue 4/29

8:25 pm-3:25 pm

1 stop14h 00m

Chicago O'Hare Intl

Tue 5/6

6:15 am-12:25 pm

1 stop11h 10m

$615

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Wed 5/7

8:50 pm-5:45 pm

2 stops15h 55m

Chicago Midway

Sun 5/11

6:00 am-7:25 pm

2 stops18h 25m

$846

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Sat 7/19

8:45 pm-1:40 pm

2 stops11h 55m

Chicago Midway

Wed 7/23

8:05 am-5:05 pm

1 stop14h 00m

$943

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Sat 7/19

5:10 pm-6:05 am

Nonstop7h 55m

Chicago O'Hare Intl

Wed 7/23

6:00 am-3:10 pm

1 stop14h 10m

$1,050

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Mon 5/19

8:50 pm-5:45 pm

2 stops15h 55m

$255

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Mon 5/19

12:00 pm-11:47 am

2 stops18h 47m

$255

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Mon 5/19

9:45 pm-11:59 pm

2 stops21h 14m

$265

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Mon 5/19

8:25 pm-11:45 am

1 stop10h 20m

$327

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/23

Showing 1-10 of 13 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 April 24, 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.

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 April 24, 2025.
Get a feel of what it's like to fly with Alaska Airlines, Southwest and Delta from Maui to Chicago by reading reviews from past customers. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
9,918 reviews

Crew

8.5

Food

7.1

Boarding

8.2

Entertainment

7.1

Overall

8.0

Comfort

7.9

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Alaska Airlines
8.0
Very good
9,918 reviews
Alaska Airlines
8.0
Very good
9,918 reviews

Crew

8.5

Food

7.1

Boarding

8.2

Entertainment

7.1

Overall

8.0

Comfort

7.9

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Southwest
8.0
Very good
4,286 reviews
Alaska Airlines
8.0
Very good
9,918 reviews

Crew

8.5

Food

7.1

Boarding

8.2

Entertainment

7.1

Overall

8.0

Comfort

7.9

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Delta
8.0
Very good
7,920 reviews
Alaska Airlines
8.0
Very good
9,918 reviews

Crew

8.5

Food

7.1

Boarding

8.2

Entertainment

7.1

Overall

8.0

Comfort

7.9

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
United Airlines
7.4
Good
8,685 reviews
Alaska Airlines
8.0
Very good
9,918 reviews

Crew

8.5

Food

7.1

Boarding

8.2

Entertainment

7.1

Overall

8.0

Comfort

7.9

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
American Airlines
7.2
Good
10,000 reviews
Alaska Airlines
8.0
Very good
9,918 reviews

Crew

8.5

Food

7.1

Boarding

8.2

Entertainment

7.1

Overall

8.0

Comfort

7.9

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >

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 Delta. According to our data, you can fly for as low as $254. Users have also found prices from $265 and $319 on Alaska Airlines and United Airlines, respectively.

  • What are the cheapest flights from Maui to Chicago?

    The cheapest flight price from Maui to Chicago is $316. On average you can expect to pay $868. The most popular route, (Kahului - Chicago O'Hare Intl), can usually be booked for $594.

  • 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
Hammond
Benton Harbor
Porter
Lansing
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 April 24, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$282Average$541FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$349Average$538FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$432Average$734FlexibilityNo cancel feeOn-time69%
Alaska AirlinesCheapest$495Average$715FlexibilityNo cancel feeOn-time75%

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