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$219+ 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 8/12. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — OGG
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
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 June 12, 2025.

Round-trip from

$629
(Trip.com)

One-way from

$219
(American Airlines)

Popular in

March

Cheapest in

September

Average price

$786

Good round-trip deal

$1,043 or less

Good one-way deal

$577 or less
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 ($105 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 June 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 June 12, 2025.

This Trip.com deal was found by Cheapflights users on 6/11. 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 7/142:03 pmORD - OGG
1 stop11h 36mMultiple Airlines
Mon 7/213:20 pmOGG - ORD
1 stop17h 53mMultiple Airlines
Deal found 6/11$629
This Hawaiian Airlines deal was found by Cheapflights users on 6/10. 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.
Thu 7/242:03 pmORD - OGG
1 stop11h 36mHawaiian Airlines
Mon 7/2810:34 pmOGG - ORD
1 stop13h 23mHawaiian Airlines
Deal found 6/10$633
This Alaska Airlines deal was found by Cheapflights users on 6/12. 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.
Fri 9/191:01 pmORD - OGG
2 stops14h 10mAlaska Airlines
Tue 9/3012:24 pmOGG - ORD
2 stops13h 39mAlaska Airlines
Deal found 6/12$635
This American Airlines deal was found by Cheapflights users on 6/9. 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.
Mon 12/17:00 amORD - OGG
1 stop12h 20mAmerican Airlines
Wed 12/102:49 pmOGG - ORD
1 stop11h 20mAmerican Airlines
Deal found 6/9$640
This Southwest deal was found by Cheapflights users on 6/10. 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 8/136:10 amMDW - OGG
1 stop11h 15mSouthwest
Sun 8/178:30 pmOGG - MDW
1 stop11h 55mSouthwest
Deal found 6/10$642
This Delta deal was found by Cheapflights users on 6/11. 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.
Mon 10/67:15 amORD - OGG
2 stops14h 41mDelta
Fri 10/109:10 pmOGG - ORD
2 stops14h 37mDelta
Deal found 6/11$654
This Delta deal was found by Cheapflights users on 6/11. 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 11/116:00 amMDW - OGG
1 stop15h 30mDelta
Sat 11/225:25 pmOGG - MDW
1 stop12h 26mDelta
Deal found 6/11$656
This Orbitz deal was found by Cheapflights users on 6/11. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/86:00 amORD - HNM
2 stops15h 33mMultiple Airlines
Tue 10/144:55 pmHNM - ORD
2 stops16h 55mMultiple Airlines
Deal found 6/11$801
This Southwest deal was found by Cheapflights users on 6/10. 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 7/236:15 amORD - OGG
2 stops15h 15mSouthwest
Wed 7/308:45 pmOGG - ORD
2 stops15h 00mSouthwest
Deal found 6/10$814
This Orbitz deal was found by Cheapflights users on 6/11. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/293:20 pmORD - JHM
3 stops27h 30mMultiple Airlines
Tue 11/42:10 pmJHM - ORD
2 stops18h 54mMultiple Airlines
Deal found 6/11$1,042

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 June 12, 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

Mon 7/14

2:03 pm-8:39 pm

1 stop11h 36m

Kahului

Mon 7/21

3:20 pm-2:13 pm

1 stop17h 53m

$629

ChicagoKahului

ORD - OGG

ORDOGG

Chicago O'Hare Intl

Thu 7/24

2:03 pm-8:39 pm

1 stop11h 36m

Kahului

Mon 7/28

10:34 pm-4:57 pm

1 stop13h 23m

$633

ChicagoKahului

ORD - OGG

ORDOGG

Chicago O'Hare Intl

Thu 7/24

2:03 pm-8:39 pm

1 stop11h 36m

Kahului

Thu 7/31

8:47 am-5:40 am

2 stops15h 53m

$638

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Wed 8/13

6:10 am-12:25 pm

1 stop11h 15m

Kahului

Sun 8/17

8:30 pm-1:25 pm

1 stop11h 55m

$642

ChicagoKahului

ORD - OGG

ORDOGG

Chicago O'Hare Intl

Mon 8/18

8:25 am-5:08 pm

2 stops13h 43m

Kahului

Sun 8/24

9:09 pm-5:30 pm

2 stops15h 21m

$654

ChicagoKahului

ORD - OGG

ORDOGG

Chicago O'Hare Intl

Sun 8/24

10:25 am-8:24 pm

2 stops14h 59m

Kahului

Sun 8/31

9:46 pm-1:44 pm

1 stop10h 58m

$692

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Sat 8/9

9:24 am-7:33 pm

2 stops15h 09m

Kahului

Mon 9/8

9:10 pm-5:37 pm

2 stops15h 27m

$699

ChicagoKahului

ORD - OGG

ORDOGG

Chicago O'Hare Intl

Thu 8/21

5:00 am-6:59 pm

2 stops18h 59m

Kahului

Thu 8/28

12:15 pm-9:41 am

2 stops16h 26m

$793

ChicagoKahului

ORD - OGG

ORDOGG

Chicago O'Hare Intl

Wed 7/23

6:15 am-4:30 pm

2 stops15h 15m

Kahului

Wed 7/30

8:45 pm-4:45 pm

2 stops15h 00m

$814

ChicagoHana

ORD - HNM

ORDHNM

Chicago O'Hare Intl

Fri 7/25

2:03 pm-8:33 am

2 stops23h 30m

Hana

Fri 8/1

4:55 pm-5:40 am

2 stops31h 45m

$1,015

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/11

Showing 1-10 of 20 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 June 12, 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 June 12, 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
10,000 reviews

Entertainment

7.1

Crew

8.5

Overall

8.0

Comfort

7.8

Boarding

8.1

Food

7.1

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
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Entertainment

7.1

Crew

8.5

Overall

8.0

Comfort

7.8

Boarding

8.1

Food

7.1

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
4,287 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Entertainment

7.1

Crew

8.5

Overall

8.0

Comfort

7.8

Boarding

8.1

Food

7.1

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
7,950 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Entertainment

7.1

Crew

8.5

Overall

8.0

Comfort

7.8

Boarding

8.1

Food

7.1

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
2,494 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Entertainment

7.1

Crew

8.5

Overall

8.0

Comfort

7.8

Boarding

8.1

Food

7.1

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
8,790 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Entertainment

7.1

Crew

8.5

Overall

8.0

Comfort

7.8

Boarding

8.1

Food

7.1

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 American Airlines. According to our data, you can fly for as low as $219. Users have also found prices from $265 and $265 on Southwest and Alaska 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 $577. While the most popular route (Chicago O'Hare Intl - Kahului) can be booked for $437 on average our data indicates $1,665 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
O'Hare Intl to Kahului flights
Midway to Honolulu flights
O'Hare Intl to Lihue flights
St. Louis to Honolulu flights
O'Hare Intl to Kailua-Kona flights
Midway to Kahului flights
St. Louis to Kahului flights
Midway to Lihue flights
Midway to Kailua-Kona flights
St. Louis to Lihue flights
O'Hare Intl to Hilo flights
St. Louis to Kailua-Kona flights
Moline to Honolulu flights
Evansville to Honolulu flights
Peoria to Honolulu flights
Bloomington to Honolulu flights
Decatur to Honolulu flights
Midway to Hilo flights
Moline to Kahului flights
O'Hare Intl to Kapalua flights
Evansville to Kahului flights
Moline to Hilo flights
St. Louis to Hilo flights
St. Louis to Kapalua flights
Peoria to Kahului flights
Bloomington to Kahului flights
Peoria to Lihue flights
Champaign to Honolulu flights
O'Hare Intl to Waimea (Big Island) flights
Dubuque to Honolulu flights
Moline to Kailua-Kona flights
Bloomington to Lihue flights
Evansville to Lihue flights
St. Louis to Waimea (Big Island) flights
St. Louis to Hana flights
Springfield to Kahului flights
Springfield to Lihue flights
Springfield to Honolulu flights
O'Hare Intl to Hana flights
Champaign to Kailua-Kona flights
Moline to Lihue flights

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 June 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$330Average$538FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$349Average$642FlexibilityNo cancel feeOn-time71%
Alaska AirlinesCheapest$422Average$631FlexibilityNo cancel feeOn-time75%
Hawaiian AirlinesCheapest$448Average$711FlexibilityNo cancel feeOn-time85%
United AirlinesCheapest$471Average$1,044FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$498Average$739FlexibilityNo cancel feeOn-time63%

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