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$211+ 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 11/11. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — OGG
Aug 19 — Aug 261
Tue 8/19
Tue 8/26
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 August 14, 2025.

Round-trip from

$521
(Southwest)

One-way from

$211
(Southwest)

Popular in

March

Cheapest in

November

Average price

$689
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. 11% potential increase in price ($90 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 August 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 August 14, 2025.

This Southwest deal was found by Cheapflights users on 8/12. 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.
Mon 10/277:45 amMDW - OGG
1 stop13h 45mSouthwest
Mon 11/39:35 pmOGG - MDW
1 stop12h 05mSouthwest
Deal found 8/12$476
This Southwest deal was found by Cheapflights users on 8/11. 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.
Mon 10/277:45 amMDW - OGG
1 stop13h 45mSouthwest
Fri 10/315:45 pmOGG - MDW
2 stops13h 15mSouthwest
Deal found 8/11$484
This Southwest deal was found by Cheapflights users on 8/12. 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.
Wed 10/296:25 amMDW - OGG
1 stop11h 35mSouthwest
Tue 11/49:35 pmOGG - MDW
1 stop10h 00mSouthwest
Deal found 8/12$499
This Southwest deal was found by Cheapflights users on 8/11. 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.
Tue 9/26:10 amMDW - OGG
1 stop11h 15mSouthwest
Wed 9/108:30 pmOGG - MDW
1 stop11h 55mSouthwest
Deal found 8/11$506
This Delta deal was found by Cheapflights users on 8/12. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/276:00 amMDW - OGG
2 stops17h 18mDelta
Mon 11/310:09 pmOGG - MDW
2 stops15h 34mDelta
Deal found 8/12$524
This Southwest deal was found by Cheapflights users on 8/13. 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 9/295:15 amMDW - OGG
1 stop12h 10mSouthwest
Wed 10/88:30 pmOGG - MDW
1 stop11h 50mSouthwest
Deal found 8/13$549
This Southwest deal was found by Cheapflights users on 8/13. 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 9/227:10 amMDW - OGG
2 stops14h 20mSouthwest
Wed 10/18:25 pmOGG - MDW
1 stop11h 25mSouthwest
Deal found 8/13$554

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 August 14, 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

Mon 10/27

7:45 am-4:30 pm

1 stop13h 45m

Kahului

Mon 11/3

9:35 pm-1:40 pm

1 stop12h 05m

$476

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Mon 10/27

7:45 am-4:30 pm

1 stop13h 45m

Kahului

Fri 10/31

5:45 pm-12:00 pm

2 stops13h 15m

$484

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Wed 10/29

6:25 am-1:00 pm

1 stop11h 35m

Kahului

Tue 11/4

9:35 pm-11:35 am

1 stop10h 00m

$499

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Tue 9/2

6:10 am-12:25 pm

1 stop11h 15m

Kahului

Wed 9/10

8:30 pm-1:25 pm

1 stop11h 55m

$506

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Mon 10/27

6:00 am-6:18 pm

2 stops17h 18m

Kahului

Mon 11/3

10:09 pm-5:43 pm

2 stops15h 34m

$524

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Mon 9/29

5:15 am-12:25 pm

1 stop12h 10m

Kahului

Wed 10/8

8:30 pm-1:20 pm

1 stop11h 50m

$549

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Mon 9/22

7:10 am-4:30 pm

2 stops14h 20m

Kahului

Wed 10/1

8:25 pm-12:50 pm

1 stop11h 25m

$554

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Tue 11/11

5:15 am-2:50 pm

2 stops13h 35m

$211

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Mon 9/29

7:03 pm-10:05 am

1 stop20h 02m

$239

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Wed 10/29

6:25 am-1:00 pm

1 stop11h 35m

$250

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/12

Showing 1-10 of 13 results
1
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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

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.

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 August 14, 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
4,244 reviews

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Food

7.0

Overall

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Southwest
8.0
Very good
4,244 reviews
Southwest
8.0
Very good
4,244 reviews

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Food

7.0

Overall

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.

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.

  • 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

Browse thousands of different options on Cheapflights for your next trip

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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 August 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$498Average$748FlexibilityNo cancel feeOn-time63%

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