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Maui

$232+ 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 5/6. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — OGG
Apr 9 — Apr 161
Wed 4/9
Wed 4/16
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 4, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$528
(Alaska Airlines)

One-way from

$232
(Alaska Airlines)

Popular in

March

Cheapest in

September

Average price

$645

Good round-trip deal

$1,053 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. 10% potential increase in price ($81 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 4, 2025.

This Alaska Airlines deal was found by Cheapflights users on 4/4. 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 5/247:59 pmORD - OGG
1 stop20h 11mAlaska Airlines
Mon 6/910:34 pmOGG - ORD
1 stop26h 06mAlaska Airlines
Deal found 4/4$528
This Delta deal was found by Cheapflights users on 4/4. 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 5/67:50 amORD - OGG
2 stops16h 51mDelta
Tue 5/1312:00 pmOGG - ORD
2 stops16h 51mDelta
Deal found 4/4$530
This Delta deal was found by Cheapflights users on 4/4. 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 5/610:20 amMDW - OGG
2 stops14h 21mDelta
Tue 5/1312:00 pmOGG - MDW
2 stops15h 40mDelta
Deal found 4/4$532
This Hawaiian Airlines deal was found by Cheapflights users on 4/4. 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.
Sun 8/176:00 amORD - OGG
1 stop12h 40mHawaiian Airlines
Mon 8/258:00 amOGG - ORD
1 stop10h 59mHawaiian Airlines
Deal found 4/4$532
This Southwest deal was found by Cheapflights users on 4/3. 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.
Mon 5/125:05 amMDW - OGG
1 stop12h 55mSouthwest
Mon 5/198:30 pmOGG - MDW
1 stop14h 15mSouthwest
Deal found 4/3$597
This Southwest deal was found by Cheapflights users on 4/3. 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.
Mon 4/216:15 amORD - OGG
2 stops15h 30mSouthwest
Mon 4/288:25 pmOGG - ORD
1 stop14h 00mSouthwest
Deal found 4/3$613
This United Airlines deal was found by Cheapflights users on 4/3. 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.
Wed 8/66:30 amORD - OGG
1 stop14h 52mUnited Airlines
Sat 8/167:00 amOGG - ORD
1 stop17h 18mUnited Airlines
Deal found 4/3$654
This eDestinos deal was found by Cheapflights users on 4/4. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/197:59 pmORD - JHM
2 stops22h 51mMultiple Airlines
Mon 5/262:10 pmJHM - ORD
2 stops34h 30mMultiple Airlines
Deal found 4/4$977
This Trip.com deal was found by Cheapflights users on 4/4. 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.
Mon 5/196:00 amORD - HNM
2 stops15h 33mMultiple Airlines
Mon 5/264:55 pmHNM - ORD
2 stops31h 45mMultiple Airlines
Deal found 4/4$1,072

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 4, 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

Sat 5/24

7:59 pm-11:10 am

1 stop20h 11m

Kahului

Mon 6/9

10:34 pm-5:40 am

1 stop26h 06m

$528

ChicagoKahului

ORD - OGG

ORDOGG

Chicago O'Hare Intl

Tue 5/6

7:50 am-7:41 pm

2 stops16h 51m

Kahului

Tue 5/13

12:00 pm-9:51 am

2 stops16h 51m

$530

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Tue 5/6

10:20 am-7:41 pm

2 stops14h 21m

Kahului

Tue 5/13

12:00 pm-8:40 am

2 stops15h 40m

$532

ChicagoKahului

ORD - OGG

ORDOGG

Chicago O'Hare Intl

Sun 5/4

6:00 am-1:20 pm

1 stop12h 20m

Kahului

Sun 5/11

11:55 am-6:05 am

1 stop13h 10m

$581

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Mon 5/12

5:05 am-1:00 pm

1 stop12h 55m

Kahului

Mon 5/19

8:30 pm-3:45 pm

1 stop14h 15m

$597

ChicagoKahului

ORD - OGG

ORDOGG

Chicago O'Hare Intl

Mon 4/21

6:15 am-4:45 pm

2 stops15h 30m

Kahului

Mon 4/28

8:25 pm-3:25 pm

1 stop14h 00m

$613

ChicagoKahului

ORD - OGG

ORDOGG

Chicago O'Hare Intl

Tue 6/10

7:20 am-7:34 pm

2 stops17h 14m

Kahului

Tue 6/17

7:15 am-5:45 am

2 stops17h 30m

$706

ChicagoKapalua

ORD - JHM

ORDJHM

Chicago O'Hare Intl

Mon 5/19

7:59 pm-1:50 pm

2 stops22h 51m

Kapalua West Maui

Mon 5/26

2:10 pm-5:40 am

2 stops34h 30m

$977

ChicagoHana

ORD - HNM

ORDHNM

Chicago O'Hare Intl

Mon 5/19

6:00 am-4:33 pm

2 stops15h 33m

Hana

Mon 5/26

4:55 pm-5:40 am

2 stops31h 45m

$1,072

ChicagoKahului

ORD - OGG

ORDOGG

Chicago O'Hare Intl

Tue 5/6

6:58 pm-11:25 am

1 stop21h 27m

$232

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/4

Showing 1-10 of 19 results
1
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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, 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 4, 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.

Weekly flight availability from Chicago to Maui

Explore weekly flight availability from Chicago to Maui. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated April 4, 2025.

The most flights from CHI to zzFUK are scheduled on a Monday (1 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (1 on average).

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 4, 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
9,837 reviews

Crew

8.5

Food

7.1

Overall

8.0

Comfort

7.9

Boarding

8.2

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Alaska Airlines
8.0
Very good
9,837 reviews
Alaska Airlines
8.0
Very good
9,837 reviews

Crew

8.5

Food

7.1

Overall

8.0

Comfort

7.9

Boarding

8.2

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Southwest
8.0
Very good
4,276 reviews
Alaska Airlines
8.0
Very good
9,837 reviews

Crew

8.5

Food

7.1

Overall

8.0

Comfort

7.9

Boarding

8.2

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Delta
8.0
Very good
7,899 reviews
Alaska Airlines
8.0
Very good
9,837 reviews

Crew

8.5

Food

7.1

Overall

8.0

Comfort

7.9

Boarding

8.2

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Hawaiian Airlines
7.9
Good
2,353 reviews
Alaska Airlines
8.0
Very good
9,837 reviews

Crew

8.5

Food

7.1

Overall

8.0

Comfort

7.9

Boarding

8.2

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
United Airlines
7.4
Good
8,618 reviews
Alaska Airlines
8.0
Very good
9,837 reviews

Crew

8.5

Food

7.1

Overall

8.0

Comfort

7.9

Boarding

8.2

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

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 $232. Users have also found prices from $248 and $329 on Delta and American 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 $1,703 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 4, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$341Average$540FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$349Average$641FlexibilityNo cancel feeOn-time71%
Hawaiian AirlinesCheapest$357Average$585FlexibilityNo cancel feeOn-time85%
Alaska AirlinesCheapest$419Average$621FlexibilityNo cancel feeOn-time75%
United AirlinesCheapest$471Average$1,009FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$479Average$740FlexibilityNo cancel feeOn-time63%

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