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Maui

$192+ 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 2/25. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — OGG
Feb 20 — Feb 271
Fri 2/20
Fri 2/27
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 January 21, 2026.

This Alaska Airlines deal was found by Cheapflights users on 1/20. 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 3/33:07 pm
ORD
-
OGG
1 stop12h 39m
Alaska Airlines
Tue 3/1010:54 pm
OGG
-
ORD
1 stop11h 04m
Alaska Airlines
Deal found 1/20$402
This Alaska Airlines deal was found by Cheapflights users on 1/20. 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 5/123:52 pm
ORD
-
OGG
1 stop34h 38m
Alaska Airlines
Mon 5/1810:42 pm
OGG
-
ORD
1 stop15h 04m
Alaska Airlines
Deal found 1/20$403
This Delta deal was found by Cheapflights users on 1/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/237:40 am
ORD
-
OGG
2 stops15h 35m
Delta
Tue 3/109:09 pm
OGG
-
ORD
2 stops15h 56m
Delta
Deal found 1/21$405
This Alaska Airlines deal was found by Cheapflights users on 1/21. 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 2/268:20 am
ORD
-
OGG
2 stops26h 31m
Multiple Airlines
Wed 3/42:04 pm
OGG
-
ORD
1 stop29h 55m
Multiple Airlines
Deal found 1/21$408
This Kiwi.com deal was found by Cheapflights users on 1/19. 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.
Tue 4/77:45 pm
ORD
-
OGG
2 stops39h 31m
Multiple Airlines
Tue 4/143:10 pm
OGG
-
ORD
1 stop19h 32m
Multiple Airlines
Deal found 1/19$409
This Kiwi.com deal was found by Cheapflights users on 1/18. 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 4/137:55 am
ORD
-
OGG
2 stops32h 22m
Multiple Airlines
Mon 4/203:10 pm
OGG
-
ORD
1 stop19h 32m
Multiple Airlines
Deal found 1/18$411
This Alaska Airlines deal was found by Cheapflights users on 1/18. 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 2/173:07 pm
ORD
-
OGG
1 stop12h 39m
Alaska Airlines
Wed 2/2511:54 pm
OGG
-
ORD
1 stop20h 05m
Alaska Airlines
Deal found 1/18$412
This Alaska Airlines deal was found by Cheapflights users on 1/20. 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 2/238:20 am
ORD
-
OGG
2 stops18h 01m
Multiple Airlines
Tue 3/105:31 pm
OGG
-
ORD
2 stops16h 27m
Multiple Airlines
Deal found 1/20$413
This Delta deal was found by Cheapflights users on 1/20. 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 4/147:00 am
ORD
-
OGG
2 stops17h 31m
Delta
Tue 4/219:10 pm
OGG
-
ORD
2 stops15h 54m
Delta
Deal found 1/20$414
This Alaska Airlines deal was found by Cheapflights users on 1/21. 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.
Sat 2/285:29 pm
ORD
-
OGG
1 stop33h 25m
Multiple Airlines
Fri 3/67:43 pm
OGG
-
ORD
2 stops15h 15m
Multiple Airlines
Deal found 1/21$419
This Kiwi.com deal was found by Cheapflights users on 1/20. 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.
Wed 4/83:29 pm
ORD
-
OGG
2 stops24h 48m
Multiple Airlines
Wed 4/153:10 pm
OGG
-
ORD
1 stop19h 32m
Multiple Airlines
Deal found 1/20$421
This Delta deal was found by Cheapflights users on 1/18. 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 2/166:00 am
MDW
-
OGG
1 stop13h 37m
Delta
Thu 2/261:53 pm
OGG
-
MDW
2 stops15h 01m
Delta
Deal found 1/18$428

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 January 21, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

Expedia
3 stars

Round-trip from

$402
(Alaska Airlines)

One-way from

$192
(Expedia)

Popular in

December

Cheapest in

October

Average price

$619

Good round-trip deal

$893 or less

Good one-way deal

$515 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
High demand for flights, 0% potential price rise
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($18 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
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 January 21, 2026.
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 3/3

3:07 pm-11:46 pm

1 stop12h 39m

Kahului

Tue 3/10

10:54 pm-2:58 pm

1 stop11h 04m

$402

ChicagoKahului

ORD - OGG

ORDOGG

Chicago O'Hare Intl

Mon 2/23

7:40 am-7:15 pm

2 stops15h 35m

Kahului

Tue 3/10

9:09 pm-6:05 pm

2 stops15h 56m

$405

ChicagoKahului

ORD - OGG

ORDOGG

Chicago O'Hare Intl

Mon 2/23

8:20 am-10:21 pm

2 stops18h 01m

Kahului

Tue 3/10

10:54 pm-11:59 pm

1 stop20h 05m

$408

ChicagoKahului

ORD - OGG

ORDOGG

Chicago O'Hare Intl

Thu 2/26

3:07 pm-11:46 pm

1 stop12h 39m

Kahului

Wed 3/4

2:04 pm-11:59 pm

1 stop29h 55m

$412

ChicagoKahului

ORD - OGG

ORDOGG

Chicago O'Hare Intl

Tue 3/3

8:20 am-10:21 pm

2 stops18h 01m

Kahului

Tue 3/10

7:49 pm-2:58 pm

2 stops14h 09m

$413

ChicagoKahului

ORD - OGG

ORDOGG

Chicago O'Hare Intl

Tue 4/14

7:00 am-7:31 pm

2 stops17h 31m

Kahului

Tue 4/21

9:10 pm-6:04 pm

2 stops15h 54m

$414

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Mon 2/16

6:00 am-3:37 pm

1 stop13h 37m

Kahului

Thu 2/26

1:53 pm-8:54 am

2 stops15h 01m

$428

ChicagoKahului

ORD - OGG

ORDOGG

Chicago O'Hare Intl

Thu 2/26

8:20 am-6:16 am

2 stops25h 56m

Kahului

Wed 3/4

7:43 pm-2:11 pm

2 stops14h 28m

$433

ChicagoKahului

ORD - OGG

ORDOGG

Chicago O'Hare Intl

Mon 4/20

8:20 am-10:02 pm

1 stop18h 42m

Kahului

Mon 4/27

2:37 pm-6:40 am

1 stop11h 03m

$445

ChicagoKahului

ORD - OGG

ORDOGG

Chicago O'Hare Intl

Sun 3/1

8:20 am-11:46 pm

1 stop19h 26m

Kahului

Wed 3/4

7:43 pm-2:58 pm

2 stops15h 15m

$448

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/21

Showing 1-10 of 44 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, April is the cheapest month in which you can book a flight from Chicago to Maui (average of $358). 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 January 21, 2026.

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 January 21, 2026.
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
11,775 reviews

Crew

8.5

Food

7.1

Entertainment

7.0

Boarding

8.1

Comfort

7.8

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Jan 2026

STS - LAX

Enjoyed staff assistance from ticking thru tsa , boarding and in the plane Couldn’t pick a seat except upgrading
Alaska Airlines
8.0
Very good
11,775 reviews
Alaska Airlines
8.0
Very good
11,775 reviews

Crew

8.5

Food

7.1

Entertainment

7.0

Boarding

8.1

Comfort

7.8

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Jan 2026

STS - LAX

Enjoyed staff assistance from ticking thru tsa , boarding and in the plane Couldn’t pick a seat except upgrading
Southwest
8.0
Very good
4,266 reviews
Alaska Airlines
8.0
Very good
11,775 reviews

Crew

8.5

Food

7.1

Entertainment

7.0

Boarding

8.1

Comfort

7.8

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Jan 2026

STS - LAX

Enjoyed staff assistance from ticking thru tsa , boarding and in the plane Couldn’t pick a seat except upgrading
Hawaiian Airlines
7.8
Good
2,829 reviews
Alaska Airlines
8.0
Very good
11,775 reviews

Crew

8.5

Food

7.1

Entertainment

7.0

Boarding

8.1

Comfort

7.8

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Jan 2026

STS - LAX

Enjoyed staff assistance from ticking thru tsa , boarding and in the plane Couldn’t pick a seat except upgrading
United Airlines
7.4
Good
9,191 reviews
Alaska Airlines
8.0
Very good
11,775 reviews

Crew

8.5

Food

7.1

Entertainment

7.0

Boarding

8.1

Comfort

7.8

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Jan 2026

STS - LAX

Enjoyed staff assistance from ticking thru tsa , boarding and in the plane Couldn’t pick a seat except upgrading
American Airlines
7.2
Good
11,174 reviews
Alaska Airlines
8.0
Very good
11,775 reviews

Crew

8.5

Food

7.1

Entertainment

7.0

Boarding

8.1

Comfort

7.8

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Jan 2026

STS - LAX

Enjoyed staff assistance from ticking thru tsa , boarding and in the plane Couldn’t pick a seat except upgrading

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 12h 39m. The distance between Chicago and Maui is about 4175 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 $227 and $230 on American Airlines and Alaska 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 $457. While the most popular route (Chicago O'Hare Intl - Kahului) can be booked for $370 on average, our data indicates $825 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, April is the cheapest month in which you can book a flight from Chicago to Maui (average of $358). 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
O'Hare Intl to Kahului flights
Midway to Honolulu flights
St. Louis to Honolulu flights
O'Hare Intl to Kailua-Kona flights
O'Hare Intl to Lihue flights
Midway to Kahului flights
St. Louis to Kailua-Kona flights
St. Louis to Kahului flights
Midway to Kailua-Kona flights
Midway to Lihue flights
O'Hare Intl to Hilo flights
St. Louis to Lihue flights
Midway to Hilo flights
Moline to Kahului flights
Peoria to Honolulu flights
St. Louis to Hilo flights
Evansville to Honolulu flights
Moline to Kailua-Kona flights
Moline to Honolulu flights
Peoria to Kahului flights
Bloomington to Honolulu flights
Moline to Lihue flights
Bloomington to Kahului flights
Bloomington to Lihue flights
Peoria to Lihue flights
O'Hare Intl to Waimea (Big Island) flights
Springfield to Honolulu flights
Moline to Hilo flights
O'Hare Intl to Kapalua flights
Decatur to Honolulu flights
Champaign to Honolulu flights
O'Hare Intl to Hana flights
St. Louis to Kapalua flights
Evansville to Kahului flights
St. Louis to Waimea (Big Island) flights
St. Louis to Hana flights
Champaign to Kailua-Kona flights
Springfield to Kahului flights
Springfield to Lihue flights
Dubuque to Honolulu flights
Evansville to Lihue 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 January 21, 2026.
AirlineCheapestAverageFlexibilityOn-time
Hawaiian AirlinesCheapest$307Average$675FlexibilityNo cancel feeOn-time85%
DeltaCheapest$311Average$559FlexibilityNo cancel feeOn-timeN/A
Alaska AirlinesCheapest$373Average$653FlexibilityNo cancel feeOn-time75%
American AirlinesCheapest$430Average$745FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$568Average$778FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$757Average$1,079FlexibilityNo cancel feeOn-time69%

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