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$196+ Cheap flights from Chicago (CHI) to Maui

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 10/22. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — OGG
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
1 adult, Economy
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Cheap flight deals from Chicago to Maui

Keep the following information in mind while searching for Chicago to Maui flight deals. Data was last updated September 15, 2025.

Round-trip from

$438
(Alaska Airlines)

One-way from

$196
(Alaska Airlines)

Popular in

March

Cheapest in

November

Average price

$607

Good round-trip deal

$893 or less

Good one-way deal

$467 or less
From Chicago (CHI) to Maui
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One-way flight from Chicago (CHI) to Maui
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Highest demand for flights based on searches. 9% potential increase in price ($78 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($20 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Price to beat on a round-trip flight from Chicago (CHI) to Maui.
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Price to beat on a one-way flight from Chicago (CHI) to Maui.
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Find flight deals from Chicago to Maui

Cheapest flights from Chicago to Maui
Explore the most affordable flight options available from Chicago to Maui. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 15, 2025.

This Alaska Airlines deal was found by Cheapflights users on 9/15. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/189:20 amORD - OGG
2 stops17h 49mAlaska Airlines
Sun 11/2311:50 pmOGG - ORD
1 stop16h 03mAlaska Airlines
Deal found 9/15$438
This Alaska Airlines deal was found by Cheapflights users on 9/15. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/108:59 pmORD - OGG
1 stop29h 51mAlaska Airlines
Fri 11/214:40 pmOGG - ORD
1 stop26h 52mAlaska Airlines
Deal found 9/15$453
This Hawaiian Airlines deal was found by Cheapflights users on 9/15. 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 Hawaiian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/172:54 pmORD - OGG
1 stop11h 56mHawaiian Airlines
Sun 11/2311:50 pmOGG - ORD
1 stop10h 35mHawaiian Airlines
Deal found 9/15$454
This Alaska Airlines deal was found by Cheapflights users on 9/13. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/99:20 amORD - OGG
1 stop17h 30mAlaska Airlines
Thu 11/206:00 amOGG - ORD
2 stops13h 59mAlaska Airlines
Deal found 9/13$459
This Alaska Airlines deal was found by Cheapflights users on 9/13. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/23:05 pmORD - OGG
1 stop12h 35mAlaska Airlines
Thu 12/116:48 amOGG - ORD
2 stops13h 02mAlaska Airlines
Deal found 9/13$460
This Alaska Airlines deal was found by Cheapflights users on 9/13. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/82:54 pmORD - OGG
1 stop11h 56mAlaska Airlines
Fri 11/1411:59 pmOGG - ORD
1 stop9h 55mAlaska Airlines
Deal found 9/13$461
This Alaska Airlines deal was found by Cheapflights users on 9/15. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/158:59 pmORD - OGG
1 stop29h 51mAlaska Airlines
Sun 11/2311:50 pmOGG - ORD
1 stop16h 03mAlaska Airlines
Deal found 9/15$462
This Delta deal was found by Cheapflights users on 9/12. 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 10/308:57 amORD - OGG
2 stops13h 35mDelta
Wed 11/51:35 pmOGG - ORD
2 stops16h 08mDelta
Deal found 9/12$463
This Alaska Airlines deal was found by Cheapflights users on 9/13. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/82:54 pmORD - OGG
1 stop11h 56mAlaska Airlines
Wed 11/197:20 pmOGG - ORD
2 stops14h 34mAlaska Airlines
Deal found 9/13$466
This Alaska Airlines deal was found by Cheapflights users on 9/15. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/18:49 pmORD - OGG
1 stop21h 57mAlaska Airlines
Wed 12/106:00 amOGG - ORD
2 stops13h 50mAlaska Airlines
Deal found 9/15$467
This Alaska Airlines deal was found by Cheapflights users on 9/13. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/27:59 pmORD - OGG
2 stops23h 09mAlaska Airlines
Wed 12/106:00 amOGG - ORD
2 stops13h 50mAlaska Airlines
Deal found 9/13$472
This Southwest deal was found by Cheapflights users on 9/13. 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.
Mon 11/175:25 amMDW - OGG
1 stop11h 40mSouthwest
Wed 11/269:25 pmOGG - MDW
1 stop13h 00mSouthwest
Deal found 9/13$479

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Maui 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 September 15, 2025.
Use the filters below to find and compare flights from Chicago to Maui that are best for you.

Fly from

Chicago

Fly to

Maui

Route

Depart

Return

Price

ChicagoKahului

ORD - OGG

ORDOGG

Chicago O'Hare Intl

Thu 12/4

3:05 pm-11:40 pm

1 stop12h 35m

Kahului

Sun 12/7

6:00 am-11:50 pm

2 stops13h 50m

$459

ChicagoKahului

ORD - OGG

ORDOGG

Chicago O'Hare Intl

Thu 10/30

8:57 am-5:32 pm

2 stops13h 35m

Kahului

Wed 11/5

1:35 pm-9:43 am

2 stops16h 08m

$463

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Mon 11/17

5:25 am-1:05 pm

1 stop11h 40m

Kahului

Wed 11/26

9:25 pm-2:25 pm

1 stop13h 00m

$479

ChicagoKahului

ORD - OGG

ORDOGG

Chicago O'Hare Intl

Wed 10/22

8:20 am-9:37 pm

2 stops18h 17m

Kahului

Wed 10/29

6:16 pm-1:09 pm

2 stops13h 53m

$485

ChicagoKahului

ORD - OGG

ORDOGG

Chicago O'Hare Intl

Fri 10/24

8:20 am-10:05 pm

1 stop18h 45m

Kahului

Thu 10/30

6:00 am-12:24 am

2 stops13h 24m

$487

ChicagoKahului

ORD - OGG

ORDOGG

Chicago O'Hare Intl

Sat 11/15

7:00 am-10:50 pm

2 stops19h 50m

Kahului

Sun 11/23

11:50 pm-7:53 pm

1 stop16h 03m

$490

ChicagoKahului

ORD - OGG

ORDOGG

Chicago O'Hare Intl

Fri 11/14

9:20 am-10:05 pm

2 stops16h 45m

Kahului

Fri 11/21

11:50 pm-11:32 pm

1 stop19h 42m

$490

ChicagoKahului

ORD - OGG

ORDOGG

Chicago O'Hare Intl

Wed 10/15

7:59 pm-10:05 pm

1 stop31h 06m

Kahului

Wed 10/29

10:59 pm-1:54 pm

1 stop9h 55m

$491

ChicagoKahului

ORD - OGG

ORDOGG

Chicago O'Hare Intl

Mon 11/3

2:54 pm-10:50 pm

1 stop11h 56m

Kahului

Mon 11/10

11:59 pm-1:54 pm

1 stop9h 55m

$495

ChicagoKahului

ORD - OGG

ORDOGG

Chicago O'Hare Intl

Mon 11/3

2:54 pm-10:50 pm

1 stop11h 56m

Kahului

Mon 11/10

11:59 pm-1:54 pm

1 stop9h 55m

$495

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

Showing 1-10 of 50 results
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Best time to book a flight from Chicago to Maui

Have a flexible travel schedule? Discover the best time to fly to Maui from Chicago 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 Chicago to Maui

What is the cheapest month to book a flight from Chicago to Maui?

Currently, November is the cheapest month in which you can book a flight from Chicago to Maui (average of $391). Flying from Chicago to Maui in June is currently the most expensive (average of $576). 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 CHI to FUK?

Find hourly flight availability from Chicago to Maui. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 15, 2025.

When flying from Chicago to Maui, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Reviews of airlines servicing Maui

Get insights into the airlines that provide service to Maui. 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 Maui. Reviews last updated September 15, 2025.
Get a feel of what it's like to fly with Alaska Airlines, Southwest, and Hawaiian Airlines from Chicago to Maui by reading reviews from past customers. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Boarding

8.1

Comfort

7.8

Crew

8.5

Overall

8.0

Entertainment

7.0

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Boarding

8.1

Comfort

7.8

Crew

8.5

Overall

8.0

Entertainment

7.0

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
Southwest
8.0
Very good
4,242 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Boarding

8.1

Comfort

7.8

Crew

8.5

Overall

8.0

Entertainment

7.0

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
Hawaiian Airlines
7.8
Good
2,723 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Boarding

8.1

Comfort

7.8

Crew

8.5

Overall

8.0

Entertainment

7.0

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
United Airlines
7.4
Good
8,929 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Boarding

8.1

Comfort

7.8

Crew

8.5

Overall

8.0

Entertainment

7.0

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
American Airlines
7.2
Good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Boarding

8.1

Comfort

7.8

Crew

8.5

Overall

8.0

Entertainment

7.0

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.

Related info for your journey

Find useful and relevant information for your journey from Chicago to Maui. 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 Chicago to Maui?

    Departing from Chicago to Maui will take you 11h 40m. The distance between Chicago and Maui is about 4184 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the most popular routes from Chicago to Maui?

    Most travelers choose Chicago O'Hare Intl - Kahului, Chicago Midway - Kahului or Chicago O'Hare Intl - Kapalua West Maui when deciding on the best route from Chicago to Maui.

  • What are the cheapest flights from Chicago to Maui?

    Looking at all options, your cheapest flight can be booked for $405. While the most popular route (Chicago O'Hare Intl - Kahului) can be booked for $402 on average, our data indicates $1,159 when flying from Chicago to Maui.

  • Can I find deals for flights from Chicago to Maui that include hotel bookings?

    Yes. In addition to deals on Chicago to Maui flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Maui?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Maui.

  • Can I find deals for business class flights from Chicago to Maui?

    Yes. Cheapflights offers flight deals from Chicago to Maui 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 Chicago to Maui?

    Currently, November is the cheapest month in which you can book a flight from Chicago to Maui (average of $391). Flying from Chicago to Maui in June is currently the most expensive (average of $576). 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

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Alternative routes for Chicago to Maui

See prices for flight routes from nearby airports that may be better suited for you.
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Top 6 airlines flying from Chicago to Maui

Discover the top 6 airlines that operate flights from Chicago to Maui. 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 September 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$341Average$547FlexibilityNo cancel feeOn-timeN/A
Hawaiian AirlinesCheapest$357Average$680FlexibilityNo cancel feeOn-time85%
American AirlinesCheapest$398Average$735FlexibilityNo cancel feeOn-time71%
Alaska AirlinesCheapest$425Average$658FlexibilityNo cancel feeOn-time75%
SouthwestCheapest$543Average$747FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$546Average$1,056FlexibilityNo cancel feeOn-time69%

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