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$357+ 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 7/16. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — OGG
Jul 1 — Jul 81
Tue 7/1
Tue 7/8
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 June 26, 2025.

Round-trip from

$622
(Southwest)

One-way from

$357
(Southwest)

Popular in

March

Cheapest in

September

Average price

$789
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. 13% potential increase in price ($104 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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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 June 26, 2025.

This Delta deal was found by Cheapflights users on 6/25. 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 6/25$616
This Southwest deal was found by Cheapflights users on 6/23. 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 9/66:15 amMDW - OGG
1 stop11h 10mSouthwest
Mon 9/88:30 pmOGG - MDW
1 stop15h 25mSouthwest
Deal found 6/23$622
This Trip.com deal was found by Cheapflights users on 6/25. 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.
Sat 8/96:20 amMDW - OGG
2 stops34h 25mMultiple Airlines
Sat 8/163:20 pmOGG - MDW
2 stops23h 21mMultiple Airlines
Deal found 6/25$828

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 June 26, 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

Sat 9/6

6:15 am-12:25 pm

1 stop11h 10m

Kahului

Mon 9/8

8:30 pm-4:55 pm

1 stop15h 25m

$622

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Wed 8/13

6:04 am-6:00 pm

2 stops16h 56m

Kahului

Tue 8/26

12:00 pm-8:50 am

2 stops15h 50m

$706

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Sat 8/9

6:20 am-11:45 am

2 stops34h 25m

Kahului

Sat 8/16

3:20 pm-7:41 pm

2 stops23h 21m

$828

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Wed 7/16

8:05 am-5:05 pm

1 stop14h 00m

$357

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Fri 8/8

9:25 am-7:33 pm

2 stops15h 08m

$472

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/24

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 June 26, 2025.
Get a feel of what it's like to fly with Southwest and Delta 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
4,276 reviews

Boarding

8.2

Entertainment

7.6

Comfort

8.0

Overall

8.0

Food

7.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Southwest
8.0
Very good
4,276 reviews
Southwest
8.0
Very good
4,276 reviews

Boarding

8.2

Entertainment

7.6

Comfort

8.0

Overall

8.0

Food

7.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Delta
8.0
Very good
7,964 reviews
Southwest
8.0
Very good
4,276 reviews

Boarding

8.2

Entertainment

7.6

Comfort

8.0

Overall

8.0

Food

7.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

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

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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 June 26, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$498Average$748FlexibilityNo cancel feeOn-time63%

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