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$229+ 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 3/2. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — OGG
feb. 4 — feb. 111
mar. 2/4
mar. 2/11
1 adult, Economy
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Cheap flight deals from Chicago to Maui

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Maui (zzFUK). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated enero 30, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$441
(Delta)

One-way from

$229
(Delta)

Popular in

March

Cheapest in

September

Average price

$573

Good round-trip deal

$1,052 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. 6% potential increase in price ($46 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($23 potential savings vs. average RT price).
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Average for round-trip flights in January 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 enero 30, 2025.

This Delta deal was found by Cheapflights users on 1/30. 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.
mar. 2/257:00 amORD - OGG
1 stop16h 55mDelta
mar. 3/42:25 pmOGG - ORD
2 stops14h 51mDelta
Deal found 1/30$441
This Mytrip deal was found by Cheapflights users on 1/30. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 3/312:48 pmORD - OGG
3 stops27h 22mMultiple Airlines
lun. 3/1010:45 amOGG - ORD
3 stops37h 00mMultiple Airlines
Deal found 1/30$444
This Delta deal was found by Cheapflights users on 1/30. 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.
mié. 2/269:33 amMDW - OGG
2 stops14h 22mDelta
lun. 3/35:25 pmOGG - MDW
1 stop12h 47mDelta
Deal found 1/30$462
This Trip.com deal was found by Cheapflights users on 1/30. 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.
mié. 5/146:00 amORD - OGG
1 stop12h 20mHawaiian Airlines
lun. 5/1912:10 pmOGG - ORD
1 stop12h 30mHawaiian Airlines
Deal found 1/30$466
This Alaska Airlines deal was found by Cheapflights users on 1/30. 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.
lun. 3/37:45 amORD - OGG
1 stop19h 11mAlaska Airlines
lun. 3/102:35 pmOGG - ORD
1 stop17h 29mAlaska Airlines
Deal found 1/30$473
This Kissandfly.com deal was found by Cheapflights users on 1/30. 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 3/36:40 amMDW - OGG
2 stops18h 03mMultiple Airlines
lun. 3/1012:30 pmOGG - MDW
2 stops22h 02mMultiple Airlines
Deal found 1/30$493
This American Airlines deal was found by Cheapflights users on 1/30. 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.
dom. 2/237:04 pmORD - OGG
1 stop22h 21mAmerican Airlines
lun. 3/32:55 pmOGG - ORD
1 stop10h 01mAmerican Airlines
Deal found 1/30$494
This Southwest deal was found by Cheapflights users on 1/30. 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.
dom. 4/206:15 amORD - OGG
1 stop11h 10mSouthwest
dom. 5/48:25 pmOGG - ORD
1 stop14h 00mSouthwest
Deal found 1/30$503
This Southwest deal was found by Cheapflights users on 1/29. 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.
mar. 2/257:20 amMDW - OGG
1 stop13h 00mSouthwest
jue. 3/68:50 amOGG - MDW
1 stop10h 40mSouthwest
Deal found 1/29$549
This United Airlines deal was found by Cheapflights users on 1/30. 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.
sáb. 8/307:55 pmORD - OGG
1 stop20h 40mUnited Airlines
vie. 9/51:10 pmOGG - ORD
1 stop17h 36mUnited Airlines
Deal found 1/30$633
This Travelocity deal was found by Cheapflights users on 1/28. 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.
jue. 2/272:00 pmORD - HNM
3 stops22h 33mMultiple Airlines
jue. 3/68:55 amHNM - ORD
2 stops16h 58mMultiple Airlines
Deal found 1/28$778
This Expedia deal was found by Cheapflights users on 1/29. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 2/285:54 pmORD - JHM
3 stops23h 56mMultiple Airlines
vie. 3/72:10 pmJHM - ORD
2 stops23h 50mMultiple Airlines
Deal found 1/29$1,145

Find flights from Chicago to Maui within your budget

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 enero 30, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

dom. 3/2

6:00 am-5:39 pm

1 stop15h 39m

Kahului

mié. 3/5

2:25 pm-8:51 am

2 stops14h 26m

$441

ChicagoKahului

ORD - OGG

ORDOGG

Chicago O'Hare Intl

mié. 2/26

7:00 am-7:55 pm

1 stop16h 55m

Kahului

lun. 3/3

9:20 pm-3:30 pm

2 stops14h 10m

$441

ChicagoKahului

ORD - OGG

ORDOGG

Chicago O'Hare Intl

lun. 3/3

12:48 pm-12:10 pm

3 stops27h 22m

Kahului

lun. 3/10

10:45 am-4:45 am

3 stops37h 00m

$444

ChicagoKahului

ORD - OGG

ORDOGG

Chicago O'Hare Intl

mié. 2/26

7:45 am-10:56 pm

1 stop19h 11m

Kahului

jue. 3/6

3:35 pm-1:04 pm

1 stop17h 29m

$464

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

lun. 3/3

6:40 am-8:43 pm

2 stops18h 03m

Kahului

lun. 3/10

12:30 pm-3:32 pm

2 stops22h 02m

$493

ChicagoKahului

ORD - OGG

ORDOGG

Chicago O'Hare Intl

dom. 2/23

7:04 pm-1:25 pm

1 stop22h 21m

Kahului

lun. 3/3

2:55 pm-4:56 am

1 stop10h 01m

$494

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

mar. 2/25

7:20 am-4:20 pm

1 stop13h 00m

Kahului

jue. 3/6

8:50 am-11:30 pm

1 stop10h 40m

$549

ChicagoKahului

ORD - OGG

ORDOGG

Chicago O'Hare Intl

mar. 2/25

7:45 am-4:57 pm

1 stop13h 12m

Kahului

jue. 3/6

3:20 pm-5:53 am

1 stop10h 33m

$549

ChicagoKahului

ORD - OGG

ORDOGG

Chicago O'Hare Intl

sáb. 4/19

6:15 am-12:25 pm

1 stop11h 10m

Kahului

lun. 4/28

8:25 pm-3:25 pm

1 stop14h 00m

$551

ChicagoKahului

ORD - OGG

ORDOGG

Chicago O'Hare Intl

jue. 3/13

6:10 pm-12:13 pm

2 stops23h 03m

Kahului

mar. 3/18

3:11 pm-2:36 pm

2 stops18h 25m

$695

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/29

Showing 1-10 of 23 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.

Travel insights for flights from Chicago to Maui

Get recent, data-driven insights about flights from Chicago to Maui including ideal travel times, pricing trends, and more.

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 enero 30, 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 enero 30, 2025.
Get a feel of what it's like to fly with Southwest, Alaska Airlines 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.
Southwest
8.1
Very good
4,585 reviews

Overall

8.1

Crew

8.7

Boarding

8.2

Food

7.1

Comfort

8.1

Entertainment

7.7

Reviews

1 / 20

6.0
Good

Lauren,Dec 2024

MCI - DCA

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Southwest
8.1
Very good
4,585 reviews
Southwest
8.1
Very good
4,585 reviews

Overall

8.1

Crew

8.7

Boarding

8.2

Food

7.1

Comfort

8.1

Entertainment

7.7

Reviews

1 / 20

6.0
Good

Lauren,Dec 2024

MCI - DCA

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Alaska Airlines
8.0
Very good
9,688 reviews
Southwest
8.1
Very good
4,585 reviews

Overall

8.1

Crew

8.7

Boarding

8.2

Food

7.1

Comfort

8.1

Entertainment

7.7

Reviews

1 / 20

6.0
Good

Lauren,Dec 2024

MCI - DCA

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Delta
8.0
Very good
8,454 reviews
Southwest
8.1
Very good
4,585 reviews

Overall

8.1

Crew

8.7

Boarding

8.2

Food

7.1

Comfort

8.1

Entertainment

7.7

Reviews

1 / 20

6.0
Good

Lauren,Dec 2024

MCI - DCA

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Hawaiian Airlines
7.9
Good
2,320 reviews
Southwest
8.1
Very good
4,585 reviews

Overall

8.1

Crew

8.7

Boarding

8.2

Food

7.1

Comfort

8.1

Entertainment

7.7

Reviews

1 / 20

6.0
Good

Lauren,Dec 2024

MCI - DCA

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

United Airlines
7.4
Good
8,913 reviews
Southwest
8.1
Very good
4,585 reviews

Overall

8.1

Crew

8.7

Boarding

8.2

Food

7.1

Comfort

8.1

Entertainment

7.7

Reviews

1 / 20

6.0
Good

Lauren,Dec 2024

MCI - DCA

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

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 Delta. According to our data, you can fly for as low as $229. Users have also found prices from $245 and $266 on Alaska Airlines 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 $486. While the most popular route (Chicago O'Hare Intl - Kahului) can be booked for $405 on average our data indicates $859 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.
O'Hare Intl to Honolulu flights
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St. Louis to Waimea (Kamuela) flights
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Top 5 airlines flying from Chicago to Maui

Discover the top 5 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 enero 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$341Average$535FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$350Average$687FlexibilityNo cancel feeOn-time71%
Alaska AirlinesCheapest$419Average$609FlexibilityNo cancel feeOn-time75%
United AirlinesCheapest$465Average$966FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$479Average$737FlexibilityNo cancel feeOn-time63%
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