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$260+ 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 5/14. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — OGG
Apr 29 — May 61
Tue 4/29
Tue 5/6
1 adult, Economy
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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 April 24, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$540
(Alaska Airlines)

One-way from

$260
(Alaska Airlines)

Popular in

March

Cheapest in

September

Average price

$712

Good round-trip deal

$1,032 or less

Good one-way deal

$577 or less
Provider with most accurate pricing for Chicago (CHI)-Kahului flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Kahului flights.
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From Chicago (CHI) to Maui
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One-way flight from Chicago (CHI) to Maui
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Highest demand for flights based on searches. 13% potential increase in price ($103 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($25 potential savings vs. average RT price).
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Average for round-trip flights in April 2025
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Price to beat on a round-trip flight from Chicago (CHI) to Maui.
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Price to beat on a one-way flight from Chicago (CHI) to Maui.
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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 April 24, 2025.

This Alaska Airlines deal was found by Cheapflights users on 4/23. 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 5/277:00 amORD - OGG
2 stops20h 13mAlaska Airlines
Tue 6/310:35 amOGG - ORD
2 stops14h 05mAlaska Airlines
Deal found 4/23$540
This American Airlines deal was found by Cheapflights users on 4/23. 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 9/66:13 amORD - OGG
1 stop10h 57mAmerican Airlines
Sat 9/1311:23 pmOGG - ORD
1 stop16h 35mAmerican Airlines
Deal found 4/23$551
This Delta deal was found by Cheapflights users on 4/23. 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 6/26:24 amORD - OGG
2 stops18h 01mDelta
Mon 6/98:55 pmOGG - ORD
2 stops17h 23mDelta
Deal found 4/23$559
This Delta deal was found by Cheapflights users on 4/23. 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 6/29:16 amMDW - OGG
2 stops15h 09mDelta
Mon 6/98:55 pmOGG - MDW
2 stops15h 45mDelta
Deal found 4/23$586
This Kiwi.com deal was found by Cheapflights users on 4/23. 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 6/22:09 pmORD - OGG
1 stop11h 37mHawaiian Airlines
Mon 6/911:55 amOGG - ORD
1 stop21h 23mHawaiian Airlines
Deal found 4/23$586
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/216:15 amORD - OGG
1 stop11h 10mSouthwest
Tue 8/268:30 pmOGG - ORD
2 stops12h 40mSouthwest
Deal found 4/22$598
This Southwest deal was found by Cheapflights users on 4/21. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/77:30 amMDW - OGG
2 stops14h 15mSouthwest
Wed 5/148:30 pmOGG - MDW
1 stop11h 05mSouthwest
Deal found 4/21$611
This Trip.com deal was found by Cheapflights users on 4/23. 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.
Sat 6/76:10 amORD - OGG
2 stops19h 36mMultiple Airlines
Sat 6/1410:34 pmOGG - ORD
2 stops19h 31mMultiple Airlines
Deal found 4/23$672
This Travelocity deal was found by Cheapflights users on 4/23. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/163:15 pmORD - HNM
3 stops22h 18mMultiple Airlines
Tue 9/238:55 amHNM - ORD
2 stops15h 45mMultiple Airlines
Deal found 4/23$939
This Orbitz deal was found by Cheapflights users on 4/23. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/229:00 pmORD - JHM
3 stops21h 50mMultiple Airlines
Thu 10/302:10 pmJHM - ORD
2 stops18h 49mMultiple Airlines
Deal found 4/23$989

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 24, 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 5/27

7:00 am-10:13 pm

2 stops20h 13m

Kahului

Tue 6/3

10:35 am-5:40 am

2 stops14h 05m

$540

ChicagoKahului

ORD - OGG

ORDOGG

Chicago O'Hare Intl

Fri 5/30

7:15 am-5:01 pm

1 stop14h 46m

Kahului

Mon 6/9

9:45 pm-1:23 pm

1 stop10h 38m

$551

ChicagoKahului

ORD - OGG

ORDOGG

Chicago O'Hare Intl

Mon 6/2

2:09 pm-8:46 pm

1 stop11h 37m

Kahului

Mon 6/9

11:55 am-2:18 pm

1 stop21h 23m

$586

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Mon 6/2

9:16 am-7:25 pm

2 stops15h 09m

Kahului

Mon 6/9

8:55 pm-5:40 pm

2 stops15h 45m

$586

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Wed 5/7

7:30 am-4:45 pm

2 stops14h 15m

Kahului

Wed 5/14

8:30 pm-12:35 pm

1 stop11h 05m

$611

ChicagoKahului

ORD - OGG

ORDOGG

Chicago O'Hare Intl

Tue 5/6

6:15 am-12:25 pm

1 stop11h 10m

Kahului

Wed 5/14

6:00 am-11:40 pm

2 stops12h 40m

$616

ChicagoKahului

ORD - OGG

ORDOGG

Chicago O'Hare Intl

Sat 6/7

6:10 am-8:46 pm

2 stops19h 36m

Kahului

Sat 6/14

10:34 pm-11:05 pm

2 stops19h 31m

$672

ChicagoKahului

ORD - OGG

ORDOGG

Chicago O'Hare Intl

Mon 6/23

6:00 am-11:47 am

1 stop10h 47m

Kahului

Thu 7/3

10:00 pm-7:29 pm

1 stop16h 29m

$746

ChicagoHana

ORD - HNM

ORDHNM

Chicago O'Hare Intl

Fri 6/6

6:00 am-4:33 pm

2 stops15h 33m

Hana

Tue 6/10

4:55 pm-6:55 pm

2 stops21h 00m

$922

ChicagoKapalua

ORD - JHM

ORDJHM

Chicago O'Hare Intl

Tue 9/16

8:42 pm-1:50 pm

3 stops22h 08m

Kapalua West Maui

Tue 9/23

2:10 pm-1:09 pm

2 stops17h 59m

$1,079

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/21

Showing 1-10 of 19 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 April 24, 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.

Rainfall in Maui by month

Plan your trip to Maui by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Maui ranges from 0.1 - 3.8 inches per month. January is typically the wettest month, when rainfall can reach 3.8 in. June is typically the driest time to visit Maui when rainfall is around 0.1 in.

Temperature in Maui by month

Plan your trip to Maui by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Maui, use this chart to help with planning. For those seeking warmer temperatures, August is the ideal time of year to visit, when temperatures reach an average of 80.6 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 71.6 F).

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 24, 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. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
9,918 reviews

Boarding

8.2

Overall

8.0

Crew

8.5

Entertainment

7.1

Comfort

7.9

Food

7.1

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Alaska Airlines
8.0
Very good
9,918 reviews
Alaska Airlines
8.0
Very good
9,918 reviews

Boarding

8.2

Overall

8.0

Crew

8.5

Entertainment

7.1

Comfort

7.9

Food

7.1

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Southwest
8.0
Very good
4,286 reviews
Alaska Airlines
8.0
Very good
9,918 reviews

Boarding

8.2

Overall

8.0

Crew

8.5

Entertainment

7.1

Comfort

7.9

Food

7.1

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Delta
8.0
Very good
7,920 reviews
Alaska Airlines
8.0
Very good
9,918 reviews

Boarding

8.2

Overall

8.0

Crew

8.5

Entertainment

7.1

Comfort

7.9

Food

7.1

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Hawaiian Airlines
7.9
Good
2,393 reviews
Alaska Airlines
8.0
Very good
9,918 reviews

Boarding

8.2

Overall

8.0

Crew

8.5

Entertainment

7.1

Comfort

7.9

Food

7.1

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
United Airlines
7.4
Good
8,685 reviews
Alaska Airlines
8.0
Very good
9,918 reviews

Boarding

8.2

Overall

8.0

Crew

8.5

Entertainment

7.1

Comfort

7.9

Food

7.1

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >

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 $260. Users have also found prices from $263 and $329 on Delta and Hawaiian 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 $505. While the most popular route (Chicago O'Hare Intl - Kahului) can be booked for $467 on average our data indicates $1,281 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

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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.
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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 24, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$341Average$542FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$349Average$649FlexibilityNo cancel feeOn-time71%
Alaska AirlinesCheapest$419Average$623FlexibilityNo cancel feeOn-time75%
Hawaiian AirlinesCheapest$448Average$669FlexibilityNo cancel feeOn-time85%
United AirlinesCheapest$476Average$1,011FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$479Average$752FlexibilityNo cancel feeOn-time63%

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