Maui

$182+ 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 11/11. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — OGG
Aug 19 — Aug 261
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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 August 14, 2025.

Round-trip from

$466
(Alaska Airlines)

One-way from

$182
(Trip.com)

Popular in

March

Cheapest in

November

Average price

$689

Good round-trip deal

$983 or less

Good one-way deal

$537 or less
From Chicago (CHI) to Maui
One-way flight from Chicago (CHI) to Maui
Highest demand for flights based on searches. 11% potential increase in price ($90 potential increase over avg. RT price).
Cheapest flight prices on average. 3% potential price decrease ($26 potential savings vs. average RT price).
Average for round-trip flights in August 2025
Price to beat on a round-trip flight from Chicago (CHI) to Maui.
Price to beat on a one-way flight from Chicago (CHI) to Maui.

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 August 14, 2025.

This Alaska Airlines deal was found by Cheapflights users on 8/12. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/57:55 pmORD - OGG
1 stop30h 53mAlaska Airlines
Thu 12/118:00 amOGG - ORD
1 stop11h 59mAlaska Airlines
Deal found 8/12$466
This American Airlines deal was found by Cheapflights users on 8/12. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/158:40 pmORD - OGG
1 stop20h 36mAmerican Airlines
Wed 11/192:46 pmOGG - ORD
1 stop11h 57mAmerican Airlines
Deal found 8/12$467
This Alaska Airlines deal was found by Cheapflights users on 8/12. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/78:20 amORD - OGG
2 stops18h 17mAlaska Airlines
Tue 10/146:30 pmOGG - ORD
2 stops15h 20mAlaska Airlines
Deal found 8/12$469
This Delta deal was found by Cheapflights users on 8/13. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/87:15 amORD - OGG
1 stop14h 53mDelta
Thu 9/189:07 pmOGG - ORD
1 stop21h 48mDelta
Deal found 8/13$471
This Delta deal was found by Cheapflights users on 8/14. 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.
Thu 9/117:10 amORD - OGG
1 stop14h 56mDelta
Thu 9/189:07 pmOGG - ORD
1 stop11h 13mDelta
Deal found 8/14$472
This Alaska Airlines deal was found by Cheapflights users on 8/14. 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 10/309:20 amORD - OGG
1 stop17h 30mAlaska Airlines
Sat 11/811:59 pmOGG - ORD
1 stop20h 00mAlaska Airlines
Deal found 8/14$474
This Alaska Airlines deal was found by Cheapflights users on 8/12. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/36:20 amORD - OGG
1 stop12h 05mAlaska Airlines
Wed 9/108:00 amOGG - ORD
1 stop11h 03mAlaska Airlines
Deal found 8/12$475
This Southwest deal was found by Cheapflights users on 8/12. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/277:45 amMDW - OGG
1 stop13h 45mSouthwest
Mon 11/39:35 pmOGG - MDW
1 stop12h 05mSouthwest
Deal found 8/12$476
This Alaska Airlines deal was found by Cheapflights users on 8/13. 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.
Wed 12/172:59 pmORD - OGG
1 stop11h 49mAlaska Airlines
Wed 12/242:07 pmOGG - ORD
1 stop12h 22mAlaska Airlines
Deal found 8/13$476
This Alaska Airlines deal was found by Cheapflights users on 8/13. 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.
Fri 11/147:59 pmORD - OGG
1 stop30h 51mAlaska Airlines
Mon 11/179:00 pmOGG - ORD
2 stops15h 30mAlaska Airlines
Deal found 8/13$477
This Alaska Airlines deal was found by Cheapflights users on 8/12. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/47:00 amORD - OGG
2 stops15h 29mAlaska Airlines
Sun 12/711:20 pmOGG - ORD
1 stop15h 35mAlaska Airlines
Deal found 8/12$478
This Alaska Airlines deal was found by Cheapflights users on 8/13. 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.
Mon 12/152:59 pmORD - OGG
1 stop11h 49mAlaska Airlines
Tue 12/2311:29 pmOGG - ORD
1 stop11h 12mAlaska Airlines
Deal found 8/13$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 August 14, 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

Tue 9/9

10:00 am-10:11 pm

2 stops17h 11m

Kahului

Wed 9/17

8:00 am-12:03 am

1 stop11h 03m

$466

ChicagoKahului

ORD - OGG

ORDOGG

Chicago O'Hare Intl

Tue 9/9

10:00 am-10:11 pm

2 stops17h 11m

Kahului

Tue 9/16

8:00 am-12:03 am

1 stop11h 03m

$466

ChicagoKahului

ORD - OGG

ORDOGG

Chicago O'Hare Intl

Tue 9/9

10:00 am-10:11 pm

2 stops17h 11m

Kahului

Mon 9/15

2:25 pm-7:03 am

1 stop11h 38m

$466

ChicagoKahului

ORD - OGG

ORDOGG

Chicago O'Hare Intl

Wed 9/10

10:00 am-10:11 pm

2 stops17h 11m

Kahului

Wed 9/17

8:00 am-12:03 am

1 stop11h 03m

$466

ChicagoKahului

ORD - OGG

ORDOGG

Chicago O'Hare Intl

Tue 10/7

8:20 am-9:37 pm

2 stops18h 17m

Kahului

Tue 10/14

6:30 pm-2:50 pm

2 stops15h 20m

$469

ChicagoKahului

ORD - OGG

ORDOGG

Chicago O'Hare Intl

Wed 9/10

7:15 am-5:08 pm

1 stop14h 53m

Kahului

Thu 9/18

9:07 pm-11:55 pm

1 stop21h 48m

$471

ChicagoKahului

ORD - OGG

ORDOGG

Chicago O'Hare Intl

Tue 9/9

7:15 am-5:08 pm

1 stop14h 53m

Kahului

Thu 9/18

9:07 pm-11:55 pm

1 stop21h 48m

$471

ChicagoKahului

ORD - OGG

ORDOGG

Chicago O'Hare Intl

Mon 9/8

7:15 am-5:08 pm

1 stop14h 53m

Kahului

Thu 9/18

9:07 pm-11:55 pm

1 stop21h 48m

$471

ChicagoKahului

ORD - OGG

ORDOGG

Chicago O'Hare Intl

Sun 9/14

6:20 am-1:25 pm

1 stop12h 05m

Kahului

Tue 9/16

9:39 pm-12:03 am

2 stops21h 24m

$471

ChicagoKahului

ORD - OGG

ORDOGG

Chicago O'Hare Intl

Thu 9/11

7:10 am-5:06 pm

1 stop14h 56m

Kahului

Thu 9/18

9:07 pm-1:20 pm

1 stop11h 13m

$472

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/12

Showing 1-10 of 46 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 August 14, 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 August 14, 2025.
Get a feel of what it's like to fly with Alaska Airlines, Southwest, and Delta 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.

Boarding

8.1

Overall

8.0

Entertainment

7.0

Comfort

7.8

Crew

8.5

Food

7.1

Reviews

1 / 20
8.0
Excellent

Anonymous,Aug 2025

BOI - LAX

flying in first class, my husband froze the entire flight and was miserable. first class does not offer blankets or any entertainment. (TV etc)

Boarding

8.1

Overall

8.0

Entertainment

7.0

Comfort

7.8

Crew

8.5

Food

7.1

Reviews

1 / 20
8.0
Excellent

Anonymous,Aug 2025

BOI - LAX

flying in first class, my husband froze the entire flight and was miserable. first class does not offer blankets or any entertainment. (TV etc)

Boarding

8.1

Overall

8.0

Entertainment

7.0

Comfort

7.8

Crew

8.5

Food

7.1

Reviews

1 / 20
8.0
Excellent

Anonymous,Aug 2025

BOI - LAX

flying in first class, my husband froze the entire flight and was miserable. first class does not offer blankets or any entertainment. (TV etc)
8.0
Very good

Boarding

8.1

Overall

8.0

Entertainment

7.0

Comfort

7.8

Crew

8.5

Food

7.1

Reviews

1 / 20
8.0
Excellent

Anonymous,Aug 2025

BOI - LAX

flying in first class, my husband froze the entire flight and was miserable. first class does not offer blankets or any entertainment. (TV etc)

Boarding

8.1

Overall

8.0

Entertainment

7.0

Comfort

7.8

Crew

8.5

Food

7.1

Reviews

1 / 20
8.0
Excellent

Anonymous,Aug 2025

BOI - LAX

flying in first class, my husband froze the entire flight and was miserable. first class does not offer blankets or any entertainment. (TV etc)

Boarding

8.1

Overall

8.0

Entertainment

7.0

Comfort

7.8

Crew

8.5

Food

7.1

Reviews

1 / 20
8.0
Excellent

Anonymous,Aug 2025

BOI - LAX

flying in first class, my husband froze the entire flight and was miserable. first class does not offer blankets or any entertainment. (TV etc)

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

    For one-way options, check prices for Hawaiian Airlines. According to our data, you can fly for as low as $182. Users have also found prices from $184 and $211 on Alaska Airlines and Southwest, respectively.

  • What are the most popular routes 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 $367 on average our data indicates $846 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

Browse thousands of different options on Cheapflights for your next trip

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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 August 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$341Average$552FlexibilityNo cancel feeOn-timeN/A
Hawaiian AirlinesCheapest$346Average$677FlexibilityNo cancel feeOn-time85%
American AirlinesCheapest$357Average$698FlexibilityNo cancel feeOn-time71%
Alaska AirlinesCheapest$438Average$666FlexibilityNo cancel feeOn-time75%
United AirlinesCheapest$496Average$1,056FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$498Average$740FlexibilityNo cancel feeOn-time63%

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