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$189+ Cheap flights from Maui to Chicago (CHI)

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 3/9. Fares are subject to change and may not be available on all flights or dates of travel.
OGG — CHI
Mar 15 — Mar 221
Sun 3/15
Sun 3/22
1 adult, Economy
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Cheap flight deals from Maui to Chicago

Cheapest flights from Maui to Chicago
Explore the most affordable flight options available from Maui to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 13, 2026.

This Alaska Airlines deal was found by Cheapflights users on 2/11. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/68:00 am
OGG
-
ORD
1 stop10h 59m
Alaska Airlines
Sat 5/167:59 pm
ORD
-
OGG
1 stop30h 31m
Alaska Airlines
Deal found 2/11$422
This Delta deal was found by Cheapflights users on 2/11. 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.
Thu 3/59:05 pm
OGG
-
ORD
1 stop11h 14m
Delta
Tue 3/249:50 am
ORD
-
OGG
1 stop13h 35m
Delta
Deal found 2/11$428
This Kiwi.com deal was found by Cheapflights users on 2/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/193:10 pm
OGG
-
ORD
1 stop32h 39m
Multiple Airlines
Tue 3/249:28 am
ORD
-
OGG
2 stops30h 02m
Multiple Airlines
Deal found 2/10$461
This Expedia deal was found by Cheapflights users on 2/11. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/51:55 pm
OGG
-
ORD
2 stops18h 06m
Multiple Airlines
Tue 3/246:00 am
ORD
-
OGG
2 stops18h 39m
Multiple Airlines
Deal found 2/11$462
This Lucky2Go deal was found by Cheapflights users on 2/11. 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 Lucky2Go is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/274:12 pm
OGG
-
ORD
2 stops35h 22m
Multiple Airlines
Tue 3/33:07 pm
ORD
-
OGG
1 stop12h 39m
Multiple Airlines
Deal found 2/11$527
This Kiwi.com deal was found by Cheapflights users on 2/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/67:15 pm
OGG
-
ORD
2 stops18h 48m
Multiple Airlines
Sat 5/169:00 am
ORD
-
OGG
1 stop17h 30m
Multiple Airlines
Deal found 2/11$560
This Alaska Airlines deal was found by Cheapflights users on 2/10. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/1911:02 pm
OGG
-
ORD
1 stop10h 19m
Alaska Airlines
Mon 3/307:59 pm
ORD
-
OGG
1 stop31h 03m
Alaska Airlines
Deal found 2/10$578
This Kiwi.com deal was found by Cheapflights users on 2/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/1910:26 am
OGG
-
ORD
2 stops33h 31m
Multiple Airlines
Mon 3/307:49 pm
ORD
-
OGG
1 stop20h 28m
Multiple Airlines
Deal found 2/12$610
This Southwest deal was found by Cheapflights users on 2/11. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/610:00 am
OGG
-
MDW
1 stop15h 00m
Southwest
Sat 5/166:55 am
MDW
-
OGG
2 stops14h 10m
Southwest
Deal found 2/11$630
This Delta deal was found by Cheapflights users on 2/11. 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.
Wed 5/610:30 pm
OGG
-
MDW
2 stops14h 26m
Delta
Sat 5/169:23 am
MDW
-
OGG
2 stops15h 12m
Delta
Deal found 2/11$639
This Southwest deal was found by Cheapflights users on 2/10. 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.
Thu 3/1910:00 am
OGG
-
MDW
1 stop14h 55m
Southwest
Tue 3/245:55 am
MDW
-
OGG
1 stop13h 20m
Southwest
Deal found 2/10$654
This Southwest deal was found by Cheapflights users on 2/12. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/279:35 pm
OGG
-
MDW
1 stop11h 55m
Southwest
Tue 3/35:05 am
MDW
-
OGG
1 stop11h 45m
Southwest
Deal found 2/12$714

Find flight deals from Maui to Chicago

Keep the following information in mind while searching for Maui to Chicago flight deals. Data was last updated February 13, 2026.

Round-trip from

$422
(Alaska Airlines)

One-way from

$189
(Kiwi.com)

Good round-trip deal

$464 or less

Good one-way deal

$292 or less
From Maui to Chicago (CHI)
Search Deals
One-way flight from Maui to Chicago (CHI)
Search Deals
Price to beat on a round-trip flight from Maui to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Maui to Chicago (CHI).
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Maui to Chicago 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 February 13, 2026.
Use the filters below to find and compare flights from Maui to Chicago that are best for you.

Fly from

Maui

Fly to

Chicago

Route

Depart

Return

Price

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Wed 5/6

8:00 am-11:59 pm

1 stop10h 59m

Chicago O'Hare Intl

Sat 5/16

7:59 pm-9:30 pm

1 stop30h 31m

$422

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Thu 3/5

9:05 pm-12:19 pm

1 stop11h 14m

Chicago O'Hare Intl

Tue 3/24

9:50 am-6:25 pm

1 stop13h 35m

$428

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Thu 3/19

3:10 pm-4:49 am

1 stop32h 39m

Chicago O'Hare Intl

Tue 3/24

9:28 am-10:30 am

2 stops30h 02m

$461

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Fri 2/27

4:12 pm-7:34 am

2 stops35h 22m

Chicago O'Hare Intl

Tue 3/3

3:07 pm-11:46 pm

1 stop12h 39m

$527

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Thu 3/19

11:02 pm-2:21 pm

1 stop10h 19m

Chicago O'Hare Intl

Mon 3/30

7:59 pm-10:02 pm

1 stop31h 03m

$578

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Thu 3/19

10:26 am-12:57 am

2 stops33h 31m

Chicago O'Hare Intl

Mon 3/30

7:49 pm-11:17 am

1 stop20h 28m

$610

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Thu 2/26

11:54 pm-2:58 pm

1 stop11h 04m

Chicago O'Hare Intl

Mon 3/2

3:07 pm-2:52 pm

1 stop27h 45m

$612

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Thu 2/26

11:54 pm-11:59 pm

1 stop20h 05m

Chicago O'Hare Intl

Mon 3/2

3:54 pm-10:35 am

2 stops22h 41m

$615

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Wed 5/6

10:00 am-6:00 am

1 stop15h 00m

Chicago Midway

Sat 5/16

6:55 am-4:05 pm

2 stops14h 10m

$630

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Thu 3/19

10:00 am-5:55 am

1 stop14h 55m

Chicago Midway

Tue 3/24

5:55 am-2:15 pm

1 stop13h 20m

$654

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/12

Showing 1-10 of 31 results
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Best time to book a flight from Maui to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Maui 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 Maui to Chicago

What is the cheapest time of day to fly from FUK to CHI?

Find hourly flight availability from Maui to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated February 13, 2026.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Maui to Chicago as you normally would.

Weekly flight availability from Maui to Chicago

Explore weekly flight availability from Maui to Chicago. 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 February 13, 2026.

The most flights from zzFUK to CHI are scheduled on a Monday (2 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (2 on average).

Related info for your journey

Find useful and relevant information for your journey from Maui to Chicago. 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 Maui to Chicago?

    There are many flights that can get you from Maui to Chicago in 10h 59m. Fly via Alaska Airlines, Delta, or Southwest to get the fastest option. The distance from Maui to Chicago is about 4175 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the cheapest airlines to fly from Maui to Chicago one-way?

    For one-way options, check prices for Southwest. According to our data, you can fly for as low as $210. Users have also found prices from $211 and $212 on Delta and American Airlines, respectively.

  • What are the cheapest flights from Maui to Chicago?

    The cheapest flight price from Maui to Chicago is $201. On average you can expect to pay $1,001. The most popular route, (Kahului - Chicago O'Hare Intl), can usually be booked for $492.

  • Can I find deals for flights from Maui to Chicago that include hotel bookings?

    Yes. In addition to deals on Maui to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Maui to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Maui to Chicago.

  • Can I find deals for business class flights from Maui to Chicago?

    Yes. Cheapflights offers flight deals from Maui to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Lansing
Merrillville
Hammond
Porter
Benton Harbor

Browse thousands of different options on Cheapflights for your next trip

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Top 3 airlines flying from Maui to Chicago

Discover the top 3 airlines that operate flights from Maui to Chicago. 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 February 13, 2026.
AirlineCheapestAverageFlexibilityOn-time
Hawaiian AirlinesCheapest$322Average$715FlexibilityNo cancel feeOn-time85%
American AirlinesCheapest$455Average$733FlexibilityNo cancel feeOn-time71%
Alaska AirlinesCheapest$468Average$683FlexibilityNo cancel feeOn-time75%

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