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$231+ Cheap flights from Midway (MDW) 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 10/23. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — OGG
Nov 1 — Nov 81
Sat 11/1
Sat 11/8
1 adult, Economy
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Cheap flight deals from Midway to Maui

Keep the following information in mind while searching for Midway to Maui flight deals. Data was last updated October 2, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$458
(Delta)

One-way from

$231
(Southwest)

Popular in

March

Cheapest in

November

Average price

$583
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 Midway to Maui
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One-way flight from Chicago Midway to Maui
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Highest demand for flights based on searches. 10% potential increase in price ($81 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 October 2025
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Find flight deals from Midway to Maui

Cheapest flights from Midway to Maui
Explore the most affordable flight options available from Midway to Maui. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 2, 2025.

This Delta deal was found by Cheapflights users on 10/1. 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.
Sun 11/96:00 amMDW - OGG
1 stop13h 28mDelta
Sun 11/165:10 pmOGG - MDW
2 stops15h 24mDelta
Deal found 10/1$458
This Southwest deal was found by Cheapflights users on 10/1. 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 11/145:30 amMDW - OGG
1 stop11h 35mSouthwest
Mon 11/249:35 pmOGG - MDW
1 stop10h 40mSouthwest
Deal found 10/1$462
This Southwest deal was found by Cheapflights users on 9/30. 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.
Thu 10/237:45 amMDW - OGG
1 stop13h 45mSouthwest
Wed 10/298:30 pmOGG - MDW
1 stop10h 45mSouthwest
Deal found 9/30$472
This Southwest deal was found by Cheapflights users on 9/30. 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.
Mon 10/276:50 amMDW - OGG
1 stop11h 00mSouthwest
Mon 11/39:35 pmOGG - MDW
2 stops13h 25mSouthwest
Deal found 9/30$486
This Southwest deal was found by Cheapflights users on 10/2. 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.
Sat 11/155:55 amMDW - OGG
1 stop11h 30mSouthwest
Sat 11/2212:45 pmOGG - MDW
2 stops12h 20mSouthwest
Deal found 10/2$503
This Delta deal was found by Cheapflights users on 9/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/76:00 amMDW - OGG
1 stop13h 00mDelta
Thu 11/135:10 pmOGG - MDW
1 stop12h 42mDelta
Deal found 9/29$512
This Southwest deal was found by Cheapflights users on 10/1. 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 10/315:55 amMDW - OGG
1 stop11h 30mSouthwest
Fri 11/79:25 pmOGG - MDW
1 stop11h 55mSouthwest
Deal found 10/1$524

Cheapflights Fare Finder

 
Customize your flight search to find flights from Midway 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 October 2, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Maui that are best for you.

Fly from

Midway

Fly to

Maui

Route

Depart

Return

Price

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Fri 11/14

5:30 am-1:05 pm

1 stop11h 35m

Kahului

Mon 11/24

9:35 pm-12:15 pm

1 stop10h 40m

$462

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Thu 10/23

7:45 am-4:30 pm

1 stop13h 45m

Kahului

Wed 10/29

8:30 pm-12:15 pm

1 stop10h 45m

$472

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Sun 11/9

6:00 am-3:28 pm

1 stop13h 28m

Kahului

Sun 11/16

8:59 pm-6:18 pm

2 stops17h 19m

$481

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Mon 10/27

6:50 am-12:50 pm

1 stop11h 00m

Kahului

Mon 11/3

9:35 pm-3:00 pm

2 stops13h 25m

$486

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Sat 11/15

5:55 am-1:25 pm

1 stop11h 30m

Kahului

Sat 11/22

12:45 pm-5:05 am

2 stops12h 20m

$503

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Fri 11/7

6:00 am-3:00 pm

1 stop13h 00m

Kahului

Thu 11/13

5:10 pm-9:52 am

1 stop12h 42m

$512

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Fri 10/31

9:35 am-6:18 pm

2 stops13h 43m

Kahului

Fri 11/7

5:10 pm-9:40 am

1 stop12h 30m

$548

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Wed 12/10

6:00 am-8:18 pm

2 stops18h 18m

Kahului

Mon 12/15

1:55 pm-9:19 am

2 stops15h 24m

$612

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Thu 10/23

7:45 am-4:30 pm

1 stop13h 45m

$231

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Sat 10/25

6:00 am-6:42 pm

2 stops17h 42m

$420

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/30

Showing 1-10 of 15 results
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Best time to book a flight from Midway to Maui

Have a flexible travel schedule? Discover the best time to fly to Maui from Midway 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 Midway Airport to Maui
No data available for this route at this time. Please check back soon.

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 October 2, 2025.
Get a feel of what it's like to fly with Southwest from Chicago Midway Airport 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.
Southwest
8.0
Very good
4,248 reviews

Overall

8.0

Food

7.0

Crew

8.6

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,248 reviews
Southwest
8.0
Very good
4,248 reviews

Overall

8.0

Food

7.0

Crew

8.6

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

Related info for your journey

Find useful and relevant information for your journey from Midway 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 Midway Airport to Maui?

    A quick flight from Chicago Midway Airport to Maui can take about 11h 35m. Southwest provides one of the quickest options available for as low as $462. Airlines will cover a distance of 4184 mi. This flight may include one or multiple stops.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Midway 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 Midway Airport to Maui?

    Currently, November is the cheapest month in which you can book a flight from Chicago Midway Airport to Maui (average of $391). Flying from Chicago Midway Airport 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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Top airline flying from Midway to Maui

Discover the top airline that operate flights from Midway 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 October 2, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$479Average$748FlexibilityNo cancel feeOn-time63%

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