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Maui

$183+ 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 12/8. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — OGG
dic. 5 — dic. 121
vie. 12/5
vie. 12/12
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 noviembre 5, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$425
(Alaska Airlines)

One-way from

$183
(Kiwi.com)

Popular in

March

Cheapest in

October

Average price

$646

Good round-trip deal

$780 or less

Good one-way deal

$497 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. 9% potential increase in price ($80 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($22 potential savings vs. average RT price).
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Average for round-trip flights in November 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 noviembre 5, 2025.

This Alaska Airlines deal was found by Cheapflights users on 11/5. 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. 12/88:55 amORD - OGG
1 stop18h 45mAlaska Airlines
vie. 12/1211:59 pmOGG - ORD
1 stop10h 10mAlaska Airlines
Deal found 11/5$425
This Alaska Airlines deal was found by Cheapflights users on 11/3. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 12/86:00 amORD - OGG
2 stops14h 58mAlaska Airlines
lun. 12/151:52 pmOGG - ORD
1 stop20h 17mAlaska Airlines
Deal found 11/3$426
This Kiwi.com deal was found by Cheapflights users on 11/4. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 12/69:06 pmORD - OGG
1 stop19h 13mMultiple Airlines
jue. 12/112:51 pmOGG - ORD
2 stops27h 16mMultiple Airlines
Deal found 11/4$427
This Alaska Airlines deal was found by Cheapflights users on 11/3. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 12/58:55 amORD - OGG
2 stops15h 31mAlaska Airlines
lun. 12/811:59 pmOGG - ORD
1 stop10h 10mAlaska Airlines
Deal found 11/3$428
This Kiwi.com deal was found by Cheapflights users on 11/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 12/79:06 pmORD - OGG
1 stop19h 13mMultiple Airlines
lun. 12/156:00 amOGG - ORD
2 stops14h 13mMultiple Airlines
Deal found 11/3$431
This Alaska Airlines deal was found by Cheapflights users on 11/3. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 12/58:55 amORD - OGG
2 stops17h 26mAlaska Airlines
mié. 12/106:00 amOGG - ORD
2 stops13h 50mAlaska Airlines
Deal found 11/3$433
This Alaska Airlines deal was found by Cheapflights users on 11/3. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 12/88:59 pmORD - OGG
1 stop30h 41mAlaska Airlines
sáb. 12/1311:59 pmOGG - ORD
1 stop19h 51mAlaska Airlines
Deal found 11/3$434
This Alaska Airlines deal was found by Cheapflights users on 11/5. 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.
sáb. 12/68:55 amORD - OGG
1 stop18h 45mAlaska Airlines
sáb. 12/131:52 pmOGG - ORD
1 stop29h 58mAlaska Airlines
Deal found 11/5$435
This Kiwi.com deal was found by Cheapflights users on 11/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 12/69:06 pmORD - OGG
1 stop19h 13mMultiple Airlines
mar. 12/96:00 amOGG - ORD
2 stops20h 05mMultiple Airlines
Deal found 11/3$436
This Alaska Airlines deal was found by Cheapflights users on 11/4. 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.
sáb. 12/68:55 amORD - OGG
1 stop18h 45mAlaska Airlines
dom. 12/1411:59 pmOGG - ORD
1 stop10h 10mAlaska Airlines
Deal found 11/4$437
This Alaska Airlines deal was found by Cheapflights users on 11/3. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 12/43:05 pmORD - OGG
1 stop12h 35mAlaska Airlines
lun. 12/156:20 pmOGG - ORD
2 stops14h 49mAlaska Airlines
Deal found 11/3$438
This Delta deal was found by Cheapflights users on 11/4. 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.
sáb. 12/67:50 amORD - OGG
2 stops15h 12mDelta
jue. 12/1110:00 pmOGG - ORD
1 stop11h 33mDelta
Deal found 11/4$439

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 noviembre 5, 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

jue. 1/29

2:06 pm-10:00 pm

1 stop11h 54m

Kahului

jue. 2/5

11:59 pm-2:29 pm

1 stop10h 30m

$432

ChicagoKahului

ORD - OGG

ORDOGG

Chicago O'Hare Intl

sáb. 12/6

8:00 am-11:40 pm

2 stops19h 40m

Kahului

mié. 12/10

6:00 am-11:50 pm

2 stops13h 50m

$435

ChicagoKahului

ORD - OGG

ORDOGG

Chicago O'Hare Intl

sáb. 12/6

8:00 am-11:40 pm

2 stops19h 40m

Kahului

lun. 12/8

11:20 pm-7:54 pm

2 stops16h 34m

$435

ChicagoKahului

ORD - OGG

ORDOGG

Chicago O'Hare Intl

mié. 1/28

3:49 pm-12:52 pm

2 stops25h 03m

Kahului

dom. 2/1

6:00 am-11:37 pm

2 stops13h 37m

$435

ChicagoKahului

ORD - OGG

ORDOGG

Chicago O'Hare Intl

sáb. 1/24

3:49 pm-10:59 pm

1 stop35h 10m

Kahului

sáb. 1/31

11:59 pm-11:37 pm

1 stop19h 38m

$435

ChicagoKahului

ORD - OGG

ORDOGG

Chicago O'Hare Intl

sáb. 1/24

9:00 am-10:59 pm

1 stop17h 59m

Kahului

sáb. 2/7

11:59 pm-2:29 pm

1 stop10h 30m

$437

ChicagoKahului

ORD - OGG

ORDOGG

Chicago O'Hare Intl

lun. 1/12

3:49 pm-2:31 pm

2 stops26h 42m

Kahului

mar. 1/20

7:06 pm-2:38 pm

2 stops15h 32m

$443

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

jue. 1/29

6:00 am-3:37 pm

1 stop13h 37m

Kahului

jue. 2/5

5:10 pm-9:58 am

1 stop12h 48m

$445

ChicagoKahului

ORD - OGG

ORDOGG

Chicago O'Hare Intl

vie. 1/30

9:00 am-10:59 pm

1 stop17h 59m

Kahului

dom. 2/8

11:59 pm-11:37 pm

1 stop19h 38m

$446

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

jue. 1/1

6:00 am-3:24 pm

1 stop13h 24m

Kahului

jue. 1/8

9:05 pm-4:31 pm

2 stops15h 26m

$451

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/4

Showing 1-10 of 37 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.

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, February is the cheapest month in which you can book a flight from Chicago to Maui (average of $367). Flying from Chicago to Maui in July is currently the most expensive (average of $632). 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 noviembre 5, 2025.

A simple way to save on the total cost of your ticket is to fly from Chicago to Maui in the afternoon. If you’re flexible enough to do this you can expect to save up to 33% on your trip compared to booking a flight in the morning.

What is the cheapest day to fly from Chicago to Maui?

Use this chart to determine the cheapest time to fly round-trip from Chicago to Maui. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Chicago to Maui flight should consider departing on Monday mornings when fares are most often at their lowest. Monday evenings flights should be avoided if possible as fares are typically the most expensive at this time.

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 noviembre 5, 2025.
Get a feel of what it's like to fly with Alaska Airlines, Southwest, and Hawaiian 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.
Alaska Airlines
8.0
Very good
11,241 reviews

Food

7.1

Entertainment

7.0

Overall

8.0

Boarding

8.1

Crew

8.5

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.
Alaska Airlines
8.0
Very good
11,241 reviews
Alaska Airlines
8.0
Very good
11,241 reviews

Food

7.1

Entertainment

7.0

Overall

8.0

Boarding

8.1

Crew

8.5

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.
Southwest
8.0
Very good
4,239 reviews
Alaska Airlines
8.0
Very good
11,241 reviews

Food

7.1

Entertainment

7.0

Overall

8.0

Boarding

8.1

Crew

8.5

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.
Hawaiian Airlines
7.8
Good
2,800 reviews
Alaska Airlines
8.0
Very good
11,241 reviews

Food

7.1

Entertainment

7.0

Overall

8.0

Boarding

8.1

Crew

8.5

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.
United Airlines
7.4
Good
9,001 reviews
Alaska Airlines
8.0
Very good
11,241 reviews

Food

7.1

Entertainment

7.0

Overall

8.0

Boarding

8.1

Crew

8.5

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.
American Airlines
7.2
Good
11,039 reviews
Alaska Airlines
8.0
Very good
11,241 reviews

Food

7.1

Entertainment

7.0

Overall

8.0

Boarding

8.1

Crew

8.5

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.

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 11h 54m. The distance between Chicago and Maui is about 4175 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • 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 $417. While the most popular route (Chicago O'Hare Intl - Kahului) can be booked for $378 on average, our data indicates $735 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, February is the cheapest month in which you can book a flight from Chicago to Maui (average of $367). Flying from Chicago to Maui in July is currently the most expensive (average of $632). 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 noviembre 5, 2025.
AirlineCheapestAverageFlexibilityOn-time
Hawaiian AirlinesCheapest$357Average$680FlexibilityNo cancel feeOn-time85%
DeltaCheapest$357Average$559FlexibilityNo cancel feeOn-timeN/A
Alaska AirlinesCheapest$394Average$651FlexibilityNo cancel feeOn-time75%
American AirlinesCheapest$410Average$740FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$479Average$756FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$593Average$1,055FlexibilityNo cancel feeOn-time69%

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