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Maui

$168+ 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 1/13. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — OGG
נוב' 20 — נוב' 271
ה' 11/20
ה' 11/27
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 אוקטובר 21, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$429
(Delta)

One-way from

$168
(Alaska Airlines)

Popular in

March

Cheapest in

October

Average price

$585

Good round-trip deal

$769 or less

Good one-way deal

$527 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 ($87 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 October 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 אוקטובר 21, 2025.

This Delta deal was found by Cheapflights users on 10/20. 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.
ב' 12/86:45 amORD - OGG
1 stop12h 39mDelta
ב' 12/810:00 pmOGG - ORD
1 stop11h 33mDelta
Deal found 10/20$429
This Alaska Airlines deal was found by Cheapflights users on 10/19. 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.
ו' 12/58:55 amORD - OGG
2 stops17h 26mAlaska Airlines
ד' 12/106:00 amOGG - ORD
2 stops13h 50mAlaska Airlines
Deal found 10/19$433
This Delta deal was found by Cheapflights users on 10/19. 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.
ש' 12/67:50 amORD - OGG
2 stops15h 12mDelta
ג' 12/910:00 pmOGG - ORD
2 stops16h 45mDelta
Deal found 10/19$434
This Alaska Airlines deal was found by Cheapflights users on 10/19. 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.
ה' 12/43:05 pmORD - OGG
1 stop12h 35mAlaska Airlines
א' 12/711:59 pmOGG - ORD
1 stop15h 55mAlaska Airlines
Deal found 10/19$435
This Alaska Airlines deal was found by Cheapflights users on 10/19. 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.
ה' 12/48:55 amORD - OGG
2 stops15h 31mAlaska Airlines
ב' 12/87:45 pmOGG - ORD
2 stops20h 09mAlaska Airlines
Deal found 10/19$436
This Delta deal was found by Cheapflights users on 10/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ג' 11/117:20 amORD - OGG
2 stops16h 47mDelta
ש' 11/2210:20 pmOGG - ORD
1 stop11h 14mDelta
Deal found 10/21$438
This Alaska Airlines deal was found by Cheapflights users on 10/19. 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.
ה' 12/113:05 pmORD - OGG
1 stop12h 35mAlaska Airlines
ג' 12/169:00 pmOGG - ORD
2 stops13h 09mAlaska Airlines
Deal found 10/19$439
This Alaska Airlines deal was found by Cheapflights users on 10/20. 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.
ו' 12/58:55 amORD - OGG
2 stops17h 26mAlaska Airlines
ה' 12/1111:59 pmOGG - ORD
1 stop10h 10mAlaska Airlines
Deal found 10/20$440
This Alaska Airlines deal was found by Cheapflights users on 10/19. 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.
ב' 11/172:54 pmORD - OGG
1 stop11h 56mAlaska Airlines
א' 11/234:40 pmOGG - ORD
1 stop26h 52mAlaska Airlines
Deal found 10/19$442
This Alaska Airlines deal was found by Cheapflights users on 10/19. 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.
ש' 11/152:54 pmORD - OGG
1 stop11h 56mAlaska Airlines
א' 11/234:40 pmOGG - ORD
1 stop26h 52mAlaska Airlines
Deal found 10/19$443
This Southwest deal was found by Cheapflights users on 10/20. 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.
ב' 11/175:25 amMDW - OGG
1 stop11h 40mSouthwest
ב' 11/249:25 pmOGG - MDW
1 stop13h 10mSouthwest
Deal found 10/20$454
This Southwest deal was found by Cheapflights users on 10/19. 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.
ה' 11/137:45 amMDW - OGG
1 stop12h 25mSouthwest
ב' 11/179:35 pmOGG - MDW
1 stop12h 05mSouthwest
Deal found 10/19$481

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 אוקטובר 21, 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

ש' 2/21

2:59 pm-10:48 pm

1 stop11h 49m

Kahului

ב' 2/23

11:20 pm-11:10 pm

1 stop19h 50m

$434

ChicagoKahului

ORD - OGG

ORDOGG

Chicago O'Hare Intl

ג' 1/6

7:30 am-7:15 pm

2 stops15h 45m

Kahului

ג' 1/13

9:00 pm-7:44 pm

2 stops18h 44m

$434

ChicagoKahului

ORD - OGG

ORDOGG

Chicago O'Hare Intl

ש' 1/31

3:25 pm-10:59 pm

1 stop11h 34m

Kahului

ו' 2/6

11:59 pm-2:29 pm

1 stop10h 30m

$435

ChicagoKahului

ORD - OGG

ORDOGG

Chicago O'Hare Intl

ב' 2/2

3:25 pm-10:59 pm

1 stop11h 34m

Kahului

ש' 2/7

11:59 pm-11:37 pm

1 stop19h 38m

$435

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

א' 2/1

6:00 am-3:30 pm

1 stop13h 30m

Kahului

ב' 2/9

5:00 pm-9:56 am

1 stop12h 56m

$442

ChicagoKahului

ORD - OGG

ORDOGG

Chicago O'Hare Intl

ש' 11/15

2:54 pm-10:50 pm

1 stop11h 56m

Kahului

א' 11/23

4:40 pm-11:32 pm

1 stop26h 52m

$443

ChicagoKahului

ORD - OGG

ORDOGG

Chicago O'Hare Intl

א' 2/1

2:06 pm-10:00 pm

1 stop11h 54m

Kahului

ש' 2/7

11:59 pm-2:29 pm

1 stop10h 30m

$444

ChicagoKahului

ORD - OGG

ORDOGG

Chicago O'Hare Intl

א' 1/25

9:00 am-10:59 pm

1 stop17h 59m

Kahului

ש' 1/31

11:59 pm-11:37 pm

1 stop19h 38m

$444

ChicagoKahului

ORD - OGG

ORDOGG

Chicago O'Hare Intl

ה' 2/19

2:59 pm-10:48 pm

1 stop11h 49m

Kahului

ש' 2/28

11:20 pm-1:59 pm

1 stop10h 39m

$444

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

ג' 1/20

5:05 am-6:10 pm

2 stops17h 05m

Kahului

ב' 1/26

9:25 pm-1:00 pm

1 stop11h 35m

$446

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/20

Showing 1-10 of 40 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, January is the cheapest month in which you can book a flight from Chicago to Maui (average of $372). Flying from Chicago to Maui in July is currently the most expensive (average of $630). 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 אוקטובר 21, 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 אוקטובר 21, 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
11,141 reviews

Crew

8.5

Food

7.1

Overall

8.0

Comfort

7.8

Entertainment

7.0

Boarding

8.1

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
11,141 reviews
Alaska Airlines
8.0
Very good
11,141 reviews

Crew

8.5

Food

7.1

Overall

8.0

Comfort

7.8

Entertainment

7.0

Boarding

8.1

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
4,235 reviews
Alaska Airlines
8.0
Very good
11,141 reviews

Crew

8.5

Food

7.1

Overall

8.0

Comfort

7.8

Entertainment

7.0

Boarding

8.1

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
2,786 reviews
Alaska Airlines
8.0
Very good
11,141 reviews

Crew

8.5

Food

7.1

Overall

8.0

Comfort

7.8

Entertainment

7.0

Boarding

8.1

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
8,988 reviews
Alaska Airlines
8.0
Very good
11,141 reviews

Crew

8.5

Food

7.1

Overall

8.0

Comfort

7.8

Entertainment

7.0

Boarding

8.1

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
11,026 reviews
Alaska Airlines
8.0
Very good
11,141 reviews

Crew

8.5

Food

7.1

Overall

8.0

Comfort

7.8

Entertainment

7.0

Boarding

8.1

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 49m. 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 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 $190. Users have also found prices from $212 and $299 on Delta and Southwest, 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 $457. While the most popular route (Chicago O'Hare Intl - Kahului) can be booked for $352 on average, our data indicates $700 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, January is the cheapest month in which you can book a flight from Chicago to Maui (average of $372). Flying from Chicago to Maui in July is currently the most expensive (average of $630). 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 אוקטובר 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
Hawaiian AirlinesCheapest$357Average$680FlexibilityNo cancel feeOn-time85%
DeltaCheapest$357Average$559FlexibilityNo cancel feeOn-timeN/A
Alaska AirlinesCheapest$402Average$650FlexibilityNo cancel feeOn-time75%
American AirlinesCheapest$405Average$738FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$479Average$754FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$560Average$1,055FlexibilityNo cancel feeOn-time69%

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