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$298+ 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 5/26. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — OGG
May 4 — May 111
Sun 5/4
Sun 5/11
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 29, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$541
(Alaska Airlines)

One-way from

$298
(Hawaiian Airlines)

Popular in

March

Cheapest in

September

Average price

$711

Good round-trip deal

$1,033 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 ($26 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 29, 2025.

This Alaska Airlines deal was found by Cheapflights users on 4/29. 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.
Wed 6/47:51 pmORD - OGG
1 stop31h 22mAlaska Airlines
Wed 6/1110:34 pmOGG - ORD
1 stop26h 06mAlaska Airlines
Deal found 4/29$545
This Delta deal was found by Cheapflights users on 4/29. 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 5/277:15 amORD - OGG
1 stop14h 46mDelta
Tue 6/109:45 pmOGG - ORD
1 stop10h 38mDelta
Deal found 4/29$548
This American Airlines deal was found by Cheapflights users on 4/29. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/76:13 amORD - OGG
1 stop10h 57mAmerican Airlines
Wed 9/175:50 pmOGG - ORD
1 stop11h 55mAmerican Airlines
Deal found 4/29$607
This Southwest deal was found by Cheapflights users on 4/29. 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.
Wed 4/306:15 amORD - OGG
1 stop11h 10mSouthwest
Wed 4/308:25 pmOGG - ORD
1 stop14h 00mSouthwest
Deal found 4/29$615
This Delta deal was found by Cheapflights users on 4/29. 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.
Sat 8/96:00 amMDW - OGG
2 stops18h 33mDelta
Mon 9/812:05 pmOGG - MDW
2 stops15h 41mDelta
Deal found 4/29$641
This Southwest deal was found by Cheapflights users on 4/29. 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.
Sun 11/97:45 amMDW - OGG
1 stop12h 25mSouthwest
Wed 11/129:35 pmOGG - MDW
1 stop11h 30mSouthwest
Deal found 4/29$645
This United Airlines deal was found by Cheapflights users on 4/29. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/113:55 pmORD - OGG
1 stop24h 55mUnited Airlines
Sat 11/228:00 amOGG - ORD
1 stop17h 10mUnited Airlines
Deal found 4/29$654
This Hawaiian Airlines deal was found by Cheapflights users on 4/29. 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 Hawaiian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/73:44 pmORD - OGG
1 stop11h 41mHawaiian Airlines
Tue 5/138:00 amOGG - ORD
1 stop10h 59mHawaiian Airlines
Deal found 4/29$665

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 29, 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

Wed 6/4

7:51 pm-10:13 pm

1 stop31h 22m

Kahului

Wed 6/11

10:34 pm-5:40 am

1 stop26h 06m

$545

ChicagoKahului

ORD - OGG

ORDOGG

Chicago O'Hare Intl

Tue 5/27

7:15 am-5:01 pm

1 stop14h 46m

Kahului

Tue 6/10

9:45 pm-1:23 pm

1 stop10h 38m

$548

ChicagoKahului

ORD - OGG

ORDOGG

Chicago O'Hare Intl

Wed 5/7

3:44 pm-10:25 pm

1 stop11h 41m

Kahului

Tue 5/13

8:00 am-11:59 pm

1 stop10h 59m

$665

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Sat 5/3

6:05 am-4:35 pm

2 stops15h 30m

Kahului

Mon 5/5

8:25 pm-11:45 am

1 stop10h 20m

$670

ChicagoKahului

ORD - OGG

ORDOGG

Chicago O'Hare Intl

Fri 5/2

6:15 am-4:45 pm

2 stops15h 30m

Kahului

Tue 5/6

8:30 pm-3:00 pm

2 stops13h 30m

$676

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Thu 5/15

9:20 am-7:25 pm

2 stops15h 05m

Kahului

Wed 5/21

12:00 pm-8:36 am

2 stops15h 36m

$720

ChicagoKahului

ORD - OGG

ORDOGG

Chicago O'Hare Intl

Sun 6/29

11:44 am-8:30 pm

1 stop13h 46m

Kahului

Tue 7/8

10:18 pm-5:02 pm

1 stop13h 44m

$772

ChicagoHana

ORD - HNM

ORDHNM

Chicago O'Hare Intl

Fri 6/13

6:00 am-4:33 pm

2 stops15h 33m

Hana

Fri 6/20

8:55 am-5:40 am

2 stops15h 45m

$1,572

ChicagoKapalua

ORD - JHM

ORDJHM

Chicago O'Hare Intl

Sat 7/19

8:34 pm-1:50 pm

3 stops22h 16m

Kapalua West Maui

Sat 8/2

2:10 pm-1:07 pm

3 stops17h 57m

$7,521

ChicagoKahului

ORD - OGG

ORDOGG

Chicago O'Hare Intl

Mon 5/26

6:00 am-2:51 pm

1 stop13h 51m

$298

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/29

Showing 1-10 of 18 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 29, 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 29, 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
9,961 reviews

Entertainment

7.1

Boarding

8.2

Comfort

7.9

Food

7.1

Crew

8.5

Overall

8.0

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
9,961 reviews
Alaska Airlines
8.0
Very good
9,961 reviews

Entertainment

7.1

Boarding

8.2

Comfort

7.9

Food

7.1

Crew

8.5

Overall

8.0

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
4,295 reviews
Alaska Airlines
8.0
Very good
9,961 reviews

Entertainment

7.1

Boarding

8.2

Comfort

7.9

Food

7.1

Crew

8.5

Overall

8.0

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
7,936 reviews
Alaska Airlines
8.0
Very good
9,961 reviews

Entertainment

7.1

Boarding

8.2

Comfort

7.9

Food

7.1

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Hawaiian Airlines
7.9
Good
2,402 reviews
Alaska Airlines
8.0
Very good
9,961 reviews

Entertainment

7.1

Boarding

8.2

Comfort

7.9

Food

7.1

Crew

8.5

Overall

8.0

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
8,696 reviews
Alaska Airlines
8.0
Very good
9,961 reviews

Entertainment

7.1

Boarding

8.2

Comfort

7.9

Food

7.1

Crew

8.5

Overall

8.0

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 Hawaiian Airlines. According to our data, you can fly for as low as $298. Users have also found prices from $303 and $336 on Alaska 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 - Hana 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 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$341Average$539FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$349Average$653FlexibilityNo cancel feeOn-time71%
Hawaiian AirlinesCheapest$357Average$685FlexibilityNo cancel feeOn-time85%
Alaska AirlinesCheapest$419Average$619FlexibilityNo cancel feeOn-time75%
United AirlinesCheapest$473Average$1,014FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$479Average$753FlexibilityNo cancel feeOn-time63%

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