HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Maui

$231+ 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 8/12. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — OGG
Jul 5 — Jul 121
Sat 7/5
Sat 7/12
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Chicago to Maui with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 June 30, 2025.

Round-trip from

$607
(Hawaiian Airlines)

One-way from

$231
(Alaska Airlines)

Popular in

March

Cheapest in

September

Average price

$789

Good round-trip deal

$983 or less

Good one-way deal

$577 or less
From Chicago (CHI) to Maui
Search Deals
One-way flight from Chicago (CHI) to Maui
Search Deals
Highest demand for flights based on searches. 13% potential increase in price ($106 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($26 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in June 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

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 June 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.
Tue 8/262:07 pmORD - OGG
2 stops24h 13mAlaska Airlines
Sun 8/3110:38 pmOGG - ORD
1 stop27h 25mAlaska Airlines
Deal found 6/29$621
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.
Tue 8/266:10 amMDW - OGG
1 stop11h 15mSouthwest
Sun 8/318:30 pmOGG - MDW
1 stop10h 50mSouthwest
Deal found 6/29$622
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.
Wed 9/107:45 amORD - OGG
2 stops14h 23mDelta
Wed 9/1712:15 pmOGG - ORD
2 stops14h 50mDelta
Deal found 6/28$624
This Trip.com 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/161:39 pmORD - OGG
2 stops26h 41mMultiple Airlines
Wed 7/2310:59 pmOGG - ORD
1 stop19h 08mMultiple Airlines
Deal found 6/29$625
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.
Tue 9/26:00 amMDW - OGG
2 stops18h 13mDelta
Tue 9/912:00 pmOGG - MDW
2 stops15h 35mDelta
Deal found 6/29$645
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/117:00 amORD - OGG
1 stop18h 24mAmerican Airlines
Mon 8/189:46 pmOGG - ORD
1 stop14h 57mAmerican Airlines
Deal found 6/28$661
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/136:15 amORD - OGG
2 stops15h 15mSouthwest
Wed 8/208:30 pmOGG - ORD
2 stops12h 35mSouthwest
Deal found 6/28$668
This Hawaiian Airlines deal was found by Cheapflights users on 6/27. 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.
Tue 7/291:03 pmORD - OGG
1 stop13h 31mHawaiian Airlines
Mon 8/48:00 amOGG - ORD
1 stop10h 59mHawaiian Airlines
Deal found 6/27$678
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/19:30 pmORD - OGG
2 stops20h 37mUnited Airlines
Fri 11/72:06 pmOGG - ORD
1 stop18h 04mUnited Airlines
Deal found 6/28$716
This Trip.com deal was found by Cheapflights users on 6/30. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/141:03 pmORD - HNM
2 stops32h 30mMultiple Airlines
Thu 8/214:55 pmHNM - ORD
2 stops33h 08mMultiple Airlines
Deal found 6/30$807
This Trip.com 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/128:42 pmORD - JHM
2 stops46h 08mMultiple Airlines
Tue 8/192:10 pmJHM - ORD
2 stops19h 14mMultiple Airlines
Deal found 6/28$938

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 June 30, 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 8/26

2:07 pm-9:20 am

2 stops24h 13m

Kahului

Sun 8/31

10:38 pm-7:03 am

1 stop27h 25m

$621

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Tue 8/26

6:10 am-12:25 pm

1 stop11h 15m

Kahului

Sun 8/31

8:30 pm-12:20 pm

1 stop10h 50m

$622

ChicagoKahului

ORD - OGG

ORDOGG

Chicago O'Hare Intl

Sat 8/9

2:03 pm-8:39 pm

1 stop11h 36m

Kahului

Mon 9/8

12:45 pm-7:03 am

1 stop13h 18m

$622

ChicagoKahului

ORD - OGG

ORDOGG

Chicago O'Hare Intl

Wed 9/10

7:45 am-5:08 pm

2 stops14h 23m

Kahului

Wed 9/17

12:15 pm-8:05 am

2 stops14h 50m

$624

ChicagoKahului

ORD - OGG

ORDOGG

Chicago O'Hare Intl

Wed 7/16

1:39 pm-11:20 am

2 stops26h 41m

Kahului

Wed 7/23

10:59 pm-11:07 pm

1 stop19h 08m

$625

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Tue 9/2

6:00 am-7:13 pm

2 stops18h 13m

Kahului

Tue 9/9

12:00 pm-8:35 am

2 stops15h 35m

$645

ChicagoKahului

ORD - OGG

ORDOGG

Chicago O'Hare Intl

Mon 8/11

7:00 am-8:24 pm

1 stop18h 24m

Kahului

Mon 8/18

9:46 pm-5:43 pm

1 stop14h 57m

$661

ChicagoKahului

ORD - OGG

ORDOGG

Chicago O'Hare Intl

Wed 8/13

6:15 am-4:30 pm

2 stops15h 15m

Kahului

Wed 8/20

8:30 pm-2:05 pm

2 stops12h 35m

$668

ChicagoHana

ORD - HNM

ORDHNM

Chicago O'Hare Intl

Thu 8/14

1:03 pm-4:33 pm

2 stops32h 30m

Hana

Thu 8/21

4:55 pm-7:03 am

2 stops33h 08m

$807

ChicagoKapalua

ORD - JHM

ORDJHM

Chicago O'Hare Intl

Tue 8/12

8:42 pm-1:50 pm

2 stops46h 08m

Kapalua West Maui

Tue 8/19

2:10 pm-2:24 pm

2 stops19h 14m

$938

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/28

Showing 1-10 of 17 results
1
2

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 June 30, 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 June 30, 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.
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Boarding

8.1

Entertainment

7.1

Crew

8.5

Overall

8.0

Food

7.1

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

Comfort

7.8

Boarding

8.1

Entertainment

7.1

Crew

8.5

Overall

8.0

Food

7.1

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

Comfort

7.8

Boarding

8.1

Entertainment

7.1

Crew

8.5

Overall

8.0

Food

7.1

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
7,973 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Boarding

8.1

Entertainment

7.1

Crew

8.5

Overall

8.0

Food

7.1

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
2,529 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Boarding

8.1

Entertainment

7.1

Crew

8.5

Overall

8.0

Food

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
United Airlines
7.4
Good
8,852 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Boarding

8.1

Entertainment

7.1

Crew

8.5

Overall

8.0

Food

7.1

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 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 Alaska Airlines. According to our data, you can fly for as low as $231. Users have also found prices from $236 and $410 on American Airlines and Delta, 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 $457. While the most popular route (Chicago O'Hare Intl - Kahului) can be booked for $461 on average our data indicates $835 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

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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
O'Hare Intl to Kahului flights
Midway to Honolulu flights
St. Louis to Honolulu flights
O'Hare Intl to Lihue flights
O'Hare Intl to Kailua-Kona flights
St. Louis to Kahului flights
Midway to Kahului flights
O'Hare Intl to Hilo flights
Midway to Lihue flights
Midway to Kailua-Kona flights
St. Louis to Lihue flights
St. Louis to Kailua-Kona flights
Midway to Hilo flights
Moline to Honolulu flights
Peoria to Honolulu flights
Bloomington to Honolulu flights
St. Louis to Hilo flights
Decatur to Honolulu flights
Evansville to Honolulu flights
O'Hare Intl to Kapalua flights
Champaign to Honolulu flights
Bloomington to Kahului flights
Peoria to Kahului flights
O'Hare Intl to Waimea (Big Island) flights
Moline to Kahului flights
O'Hare Intl to Hana flights
St. Louis to Kapalua flights
Moline to Lihue flights
Evansville to Kahului flights
Dubuque to Honolulu flights
Evansville to Lihue flights
St. Louis to Waimea (Big Island) flights
Moline to Hilo flights
Springfield to Honolulu flights
Bloomington to Lihue flights
Moline to Kailua-Kona flights
Springfield to Kahului flights
Peoria to Lihue flights
Champaign to Kailua-Kona flights
Springfield to Lihue flights
St. Louis to Hana flights

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 June 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$341Average$548FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$349Average$648FlexibilityNo cancel feeOn-time71%
Alaska AirlinesCheapest$423Average$643FlexibilityNo cancel feeOn-time75%
Hawaiian AirlinesCheapest$448Average$714FlexibilityNo cancel feeOn-time85%
United AirlinesCheapest$480Average$1,054FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$498Average$739FlexibilityNo cancel feeOn-time63%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.