Maui

$247+ 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 9/6. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — OGG
May 27 — Jun 31
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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 April 27, 2026.

This Alaska Airlines deal was found by Cheapflights users on 4/26. 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 9/166:01 am
ORD
-
OGG
2 stops20h 40m
Multiple Airlines
Thu 9/176:00 am
OGG
-
ORD
2 stops12h 41m
Multiple Airlines
Deal found 4/26$499
This Southwest deal was found by Cheapflights users on 4/27. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/266:50 am
MDW
-
OGG
1 stop10h 45m
Southwest
Wed 9/28:35 pm
OGG
-
MDW
2 stops14h 40m
Southwest
Deal found 4/27$500
This American Airlines deal was found by Cheapflights users on 4/25. 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.
Tue 9/112:11 pm
ORD
-
OGG
2 stops14h 08m
American Airlines
Tue 9/810:49 pm
OGG
-
ORD
1 stop12h 56m
American Airlines
Deal found 4/25$500
This Delta deal was found by Cheapflights users on 4/25. 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 9/16:00 am
ORD
-
OGG
2 stops16h 49m
Delta
Tue 9/88:12 pm
OGG
-
ORD
2 stops13h 46m
Delta
Deal found 4/25$505
This Cheapflightsfares deal was found by Cheapflights users on 4/27. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/286:00 am
ORD
-
OGG
1 stop12h 26m
Multiple Airlines
Thu 6/410:30 pm
OGG
-
ORD
1 stop15h 20m
Multiple Airlines
Deal found 4/27$509
This United Airlines deal was found by Cheapflights users on 4/26. 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.
Tue 5/266:13 am
ORD
-
OGG
1 stop11h 21m
United Airlines
Tue 6/21:04 pm
OGG
-
ORD
1 stop10h 47m
United Airlines
Deal found 4/26$510
This Kiwi.com deal was found by Cheapflights users on 4/26. 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 5/272:18 pm
ORD
-
OGG
1 stop11h 27m
Multiple Airlines
Thu 6/46:00 am
OGG
-
ORD
2 stops12h 55m
Multiple Airlines
Deal found 4/26$514
This Alaska Airlines deal was found by Cheapflights users on 4/25. 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 9/22:18 pm
ORD
-
OGG
1 stop12h 20m
Multiple Airlines
Tue 9/812:50 pm
OGG
-
ORD
1 stop12h 32m
Multiple Airlines
Deal found 4/25$515
This Alaska Airlines deal was found by Cheapflights users on 4/22. 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 9/16:01 am
ORD
-
OGG
1 stop20h 37m
Alaska Airlines
Tue 9/810:38 pm
OGG
-
ORD
1 stop20h 19m
Alaska Airlines
Deal found 4/22$517
This Delta deal was found by Cheapflights users on 4/26. 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 5/289:22 am
MDW
-
OGG
2 stops15h 13m
Delta
Thu 6/49:05 pm
OGG
-
MDW
2 stops15h 51m
Delta
Deal found 4/26$521
This Alaska Airlines deal was found by Cheapflights users on 4/24. 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 9/19:00 am
ORD
-
OGG
2 stops14h 24m
Multiple Airlines
Tue 9/86:00 am
OGG
-
ORD
2 stops12h 57m
Multiple Airlines
Deal found 4/24$526
This Alaska Airlines deal was found by Cheapflights users on 4/26. 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 5/272:18 pm
ORD
-
OGG
1 stop11h 27m
Alaska Airlines
Mon 6/110:30 pm
OGG
-
ORD
1 stop15h 20m
Alaska Airlines
Deal found 4/26$527

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 April 27, 2026.

Round-trip from

$499
(Alaska Airlines)

One-way from

$247
(Delta)

Popular in

December

Cheapest in

October

Average price

$843

Good round-trip deal

$914 or less

Good one-way deal

$572 or less
From Chicago (CHI) to Maui
One-way flight from Chicago (CHI) to Maui
Highest demand for flights based on searches. 1% potential increase in price ($12 potential increase over avg. RT price).
Cheapest flight prices on average. 3% potential price decrease ($24 potential savings vs. average RT price).
Average for round-trip flights in April 2026
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.

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 April 27, 2026.
Use the filters below to find and compare flights from Chicago to Maui that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Sun 5/24

9:23 am-7:35 pm

2 stops15h 12m

Kahului

Sun 5/31

8:00 pm-6:33 pm

2 stops17h 33m

$581
Quickest round-trip

ChicagoKahului

ORD - OGG

ORDOGG

Chicago O'Hare Intl

Sun 5/24

1:00 pm-7:48 pm

1 stop11h 48m

Kahului

Sun 5/31

9:59 pm-1:14 pm

1 stop10h 15m

$601

ChicagoKahului

ORD - OGG

ORDOGG

Chicago O'Hare Intl

Fri 9/4

7:00 am-5:49 pm

1 stop15h 49m

Kahului

Tue 9/8

9:10 pm-1:30 pm

1 stop11h 20m

$614

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Tue 9/1

6:50 am-4:10 pm

2 stops14h 20m

Kahului

Tue 9/8

8:55 pm-2:45 pm

2 stops12h 50m

$616

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Fri 5/29

9:22 am-7:35 pm

2 stops15h 13m

Kahului

Mon 6/8

8:05 pm-6:18 pm

2 stops17h 13m

$620

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Wed 6/3

9:23 am-7:35 pm

2 stops15h 12m

Kahului

Sun 6/7

9:50 pm-6:18 pm

2 stops15h 28m

$624

ChicagoKahului

ORD - OGG

ORDOGG

Chicago O'Hare Intl

Fri 9/4

7:00 am-5:24 pm

2 stops15h 24m

Kahului

Tue 9/8

6:00 am-11:57 pm

2 stops12h 57m

$625

ChicagoKahului

ORD - OGG

ORDOGG

Chicago O'Hare Intl

Sun 5/10

7:59 pm-1:37 pm

1 stop22h 38m

Kahului

Wed 5/20

10:30 pm-11:55 pm

1 stop20h 25m

$642

ChicagoKahului

ORD - OGG

ORDOGG

Chicago O'Hare Intl

Thu 6/4

7:40 am-3:50 pm

1 stop13h 10m

Kahului

Wed 6/10

11:03 pm-6:57 pm

1 stop14h 54m

$642

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Thu 6/4

9:22 am-7:35 pm

2 stops15h 13m

Kahului

Thu 6/11

9:50 pm-6:31 pm

2 stops15h 41m

$654

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/24

Showing 1-10 of 46 resultsSorted by cheapest first
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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

How far ahead should I book a flight from Chicago to Maui?

The best time to book flights from Chicago to Maui is 64 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

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

Currently, October is the cheapest month in which you can book a flight from Chicago to Maui (average of $220). Flying from Chicago to Maui in November is currently the most expensive (average of $402). 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 April 27, 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 April 27, 2026.
Get a feel of what it's like to fly with Southwest,Alaska Airlines, andHawaiian 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.

Crew

8.6

Entertainment

7.5

Overall

8.0

Food

7.0

Comfort

8.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

Crew

8.6

Entertainment

7.5

Overall

8.0

Food

7.0

Comfort

8.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

Crew

8.6

Entertainment

7.5

Overall

8.0

Food

7.0

Comfort

8.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

Crew

8.6

Entertainment

7.5

Overall

8.0

Food

7.0

Comfort

8.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

Crew

8.6

Entertainment

7.5

Overall

8.0

Food

7.0

Comfort

8.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

Crew

8.6

Entertainment

7.5

Overall

8.0

Food

7.0

Comfort

8.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

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 14h 20m. 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 $230 and $230 on American Airlines and Alaska Airlines, 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 $487. While the most popular route (Chicago O'Hare Intl - Kahului) can be booked for $494 on average, our data indicates $1,055 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, October is the cheapest month in which you can book a flight from Chicago to Maui (average of $220). Flying from Chicago to Maui in November is currently the most expensive (average of $402). 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 April 27, 2026.
AirlineCheapestAverageFlexibilityOn-time
Hawaiian AirlinesCheapest$295Average$675FlexibilityNo cancel feeOn-time85%
DeltaCheapest$355Average$502FlexibilityNo cancel feeOn-timeN/A
Alaska AirlinesCheapest$363Average$659FlexibilityNo cancel feeOn-time75%
American AirlinesCheapest$422Average$690FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$568Average$818FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$753Average$1,042FlexibilityNo cancel feeOn-time69%

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