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$140+ 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 1/13. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — OGG
Jan 3 — Jan 101
Sat 1/3
Sat 1/10
1 adult, Economy
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Cheap 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 December 4, 2025.

This KAYAK deal was found by Cheapflights users on 12/3. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/152:05 pmORD - OGG
1 stop12h 15mAlaska Airlines
Wed 1/2111:59 pmOGG - ORD
1 stop10h 30mAlaska Airlines
Deal found 12/3$533
This Alaska Airlines deal was found by Cheapflights users on 12/1. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/168:55 amORD - OGG
1 stop18h 45mAlaska Airlines
Wed 12/2411:59 pmOGG - ORD
1 stop16h 03mAlaska Airlines
Deal found 12/1$537
This Alaska Airlines deal was found by Cheapflights users on 12/1. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/168:55 amORD - OGG
1 stop18h 45mAlaska Airlines
Mon 12/2211:59 pmOGG - ORD
1 stop20h 00mAlaska Airlines
Deal found 12/1$539
This Kiwi.com deal was found by Cheapflights users on 12/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/156:50 amORD - OGG
2 stops35h 39mMultiple Airlines
Thu 12/254:07 pmOGG - ORD
1 stop33h 58mMultiple Airlines
Deal found 12/1$540
This Alaska Airlines deal was found by Cheapflights users on 12/1. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/152:05 pmORD - OGG
1 stop12h 15mAlaska Airlines
Wed 12/2411:59 pmOGG - ORD
1 stop10h 38mAlaska Airlines
Deal found 12/1$547
This Alaska Airlines deal was found by Cheapflights users on 12/1. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/163:05 pmORD - OGG
1 stop12h 35mAlaska Airlines
Thu 12/2511:59 pmOGG - ORD
1 stop20h 00mAlaska Airlines
Deal found 12/1$548
This Alaska Airlines deal was found by Cheapflights users on 12/1. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/152:05 pmORD - OGG
1 stop12h 15mAlaska Airlines
Mon 12/2211:59 pmOGG - ORD
1 stop20h 00mAlaska Airlines
Deal found 12/1$549
This Alaska Airlines deal was found by Cheapflights users on 12/1. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/168:00 amORD - OGG
2 stops18h 20mAlaska Airlines
Tue 12/2311:59 pmOGG - ORD
1 stop16h 03mAlaska Airlines
Deal found 12/1$557
This Alaska Airlines deal was found by Cheapflights users on 12/1. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/152:05 pmORD - OGG
1 stop12h 15mAlaska Airlines
Thu 12/2511:59 pmOGG - ORD
1 stop16h 03mAlaska Airlines
Deal found 12/1$558
This Kiwi.com deal was found by Cheapflights users on 12/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/141:52 pmORD - OGG
2 stops26h 27mMultiple Airlines
Thu 12/254:07 pmOGG - ORD
1 stop33h 58mMultiple Airlines
Deal found 12/1$563
This Southwest deal was found by Cheapflights users on 12/3. 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 12/155:15 amMDW - OGG
2 stops14h 50mSouthwest
Wed 1/219:25 pmOGG - MDW
1 stop11h 45mSouthwest
Deal found 12/3$594
This Southwest deal was found by Cheapflights users on 12/3. 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.
Tue 12/235:10 amMDW - OGG
2 stops13h 40mSouthwest
Tue 1/209:35 pmOGG - MDW
1 stop15h 00mSouthwest
Deal found 12/3$617

Find flight deals from Chicago to Maui

Keep the following information in mind while searching for Chicago to Maui flight deals. Data was last updated December 4, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$423
(Delta)

One-way from

$140
(Alaska Airlines)

Popular in

December

Cheapest in

October

Average price

$953

Good round-trip deal

$906 or less

Good one-way deal

$457 or less
Provider with most accurate pricing for Chicago (CHI)-Kahului flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Kahului flights.
Search Deals
From Chicago (CHI) to Maui
Search Deals
One-way flight from Chicago (CHI) to Maui
Search Deals
Highest demand for flights based on searches. 1% potential increase in price ($10 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($19 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals
Price to beat on a round-trip flight from Chicago (CHI) to Maui.
Search Deals
Price to beat on a one-way flight from Chicago (CHI) to Maui.
Search Deals

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 December 4, 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

MDW - OGG

MDWOGG

Chicago Midway

Mon 1/19

6:00 am-3:37 pm

1 stop13h 37m

Kahului

Thu 1/29

2:02 pm-9:08 am

2 stops15h 06m

$426

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Wed 1/21

1:49 pm-12:28 pm

2 stops26h 39m

Kahului

Thu 1/29

5:10 pm-9:53 am

1 stop12h 43m

$427

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Sun 1/11

6:45 am-3:37 pm

1 stop12h 52m

Kahului

Mon 1/19

2:02 pm-8:52 am

2 stops14h 50m

$428

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Thu 1/15

6:45 am-3:37 pm

1 stop12h 52m

Kahului

Thu 1/22

2:02 pm-8:52 am

2 stops14h 50m

$428

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Tue 1/20

1:49 pm-12:28 pm

2 stops26h 39m

Kahului

Mon 1/26

5:10 pm-9:53 am

1 stop12h 43m

$429

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Thu 1/22

6:00 am-3:37 pm

1 stop13h 37m

Kahului

Mon 1/26

2:02 pm-9:08 am

2 stops15h 06m

$430

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Mon 1/19

6:00 am-7:15 pm

2 stops17h 15m

Kahului

Wed 1/28

9:05 pm-5:55 pm

2 stops16h 50m

$432

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Tue 1/20

1:49 pm-12:28 pm

2 stops26h 39m

Kahului

Thu 1/29

2:02 pm-9:08 am

2 stops15h 06m

$433

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Sun 1/25

8:35 pm-1:10 pm

2 stops20h 35m

Kahului

Sun 2/1

9:25 pm-1:10 pm

1 stop11h 45m

$434

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Fri 2/20

5:00 am-4:25 pm

2 stops15h 25m

Kahului

Thu 2/26

7:00 pm-12:15 pm

2 stops13h 15m

$441

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/3

Showing 1-10 of 51 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, January is the cheapest month in which you can book a flight from Chicago to Maui (average of $380). Flying from Chicago to Maui in July is currently the most expensive (average of $633). 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 December 4, 2025.

A simple way to save on the total cost of your ticket is to fly from Chicago to Maui in the afternoon. If you’re flexible enough to do this you can expect to save up to 33% on your trip compared to booking a flight in the morning.

What is the cheapest day to fly from Chicago to Maui?

Use this chart to determine the cheapest time to fly round-trip from Chicago to Maui. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Chicago to Maui flight should consider departing on Monday mornings when fares are most often at their lowest. Monday evenings flights should be avoided if possible as fares are typically the most expensive at this time.

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 December 4, 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
11,400 reviews

Boarding

8.1

Crew

8.5

Food

7.1

Comfort

7.8

Entertainment

7.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Nov 2025

PDX - BNA

My family especially liked the leg room and comfortable seats.
Alaska Airlines
8.0
Very good
11,400 reviews
Alaska Airlines
8.0
Very good
11,400 reviews

Boarding

8.1

Crew

8.5

Food

7.1

Comfort

7.8

Entertainment

7.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Nov 2025

PDX - BNA

My family especially liked the leg room and comfortable seats.
Southwest
8.0
Very good
4,252 reviews
Alaska Airlines
8.0
Very good
11,400 reviews

Boarding

8.1

Crew

8.5

Food

7.1

Comfort

7.8

Entertainment

7.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Nov 2025

PDX - BNA

My family especially liked the leg room and comfortable seats.
Hawaiian Airlines
7.8
Good
2,815 reviews
Alaska Airlines
8.0
Very good
11,400 reviews

Boarding

8.1

Crew

8.5

Food

7.1

Comfort

7.8

Entertainment

7.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Nov 2025

PDX - BNA

My family especially liked the leg room and comfortable seats.
United Airlines
7.4
Good
9,066 reviews
Alaska Airlines
8.0
Very good
11,400 reviews

Boarding

8.1

Crew

8.5

Food

7.1

Comfort

7.8

Entertainment

7.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Nov 2025

PDX - BNA

My family especially liked the leg room and comfortable seats.
American Airlines
7.2
Good
11,044 reviews
Alaska Airlines
8.0
Very good
11,400 reviews

Boarding

8.1

Crew

8.5

Food

7.1

Comfort

7.8

Entertainment

7.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Nov 2025

PDX - BNA

My family especially liked the leg room and comfortable seats.

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 13h 37m. 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 cheapest airlines to fly from Chicago to Maui one-way?

    For one-way options, check prices for Delta. According to our data, you can fly for as low as $202. Users have also found prices from $202 and $230 on Hawaiian Airlines and American Airlines, respectively.

  • 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 $432. While the most popular route (Chicago O'Hare Intl - Kahului) can be booked for $282 on average, our data indicates $868 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, January is the cheapest month in which you can book a flight from Chicago to Maui (average of $380). Flying from Chicago to Maui in July is currently the most expensive (average of $633). 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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Alternative routes for Chicago to Maui

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Honolulu flights
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O'Hare Intl to Waimea (Big Island) flights
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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 December 4, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$355Average$575FlexibilityNo cancel feeOn-timeN/A
Hawaiian AirlinesCheapest$357Average$680FlexibilityNo cancel feeOn-time85%
Alaska AirlinesCheapest$398Average$652FlexibilityNo cancel feeOn-time75%
American AirlinesCheapest$426Average$754FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$568Average$763FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$714Average$1,070FlexibilityNo cancel feeOn-time69%

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