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$302+ Cheap flights from Maui to Midway (MDW)

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 9/12. Fares are subject to change and may not be available on all flights or dates of travel.
OGG — MDW
Aug 19 — Aug 261
Tue 8/19
Tue 8/26
1 adult, Economy
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Cheap flight deals from Maui to Midway

Keep the following information in mind while searching for Maui to Midway flight deals. Data was last updated August 14, 2025.

Round-trip from

$1,089
(Delta)

One-way from

$302
(Southwest)
From Maui to Chicago Midway
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One-way flight from Maui to Chicago Midway
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Find flight deals from Maui to Midway

Cheapest flights from Maui to Midway
Explore the most affordable flight options available from Maui to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 14, 2025.

This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/712:26 pmOGG - MDW
2 stops15h 14mDelta
Mon 10/139:20 amMDW - OGG
2 stops13h 58mDelta
Deal found 8/13$1,089
This Delta deal was found by Cheapflights users on 8/14. 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 8/299:10 pmOGG - MDW
2 stops15h 27mDelta
Tue 9/26:00 amMDW - OGG
2 stops16h 08mDelta
Deal found 8/14$5,422

Cheapflights Fare Finder

 
Customize your flight search to find flights from Maui to Midway 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 Maui to Chicago Midway Airport that are best for you.

Fly from

Maui

Fly to

Midway

Route

Depart

Return

Price

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Tue 10/7

12:26 pm-8:40 am

2 stops15h 14m

Chicago Midway

Mon 10/13

9:20 am-6:18 pm

2 stops13h 58m

$1,089

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Fri 8/29

9:10 pm-5:37 pm

2 stops15h 27m

Chicago Midway

Tue 9/2

6:00 am-5:08 pm

2 stops16h 08m

$5,422

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Fri 9/12

8:30 pm-11:50 am

1 stop10h 20m

$302

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Sun 11/16

6:00 am-11:30 am

3 stops25h 30m

$316

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Sun 11/16

9:35 pm-1:40 pm

1 stop12h 05m

$347

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Sat 8/30

8:30 pm-12:55 pm

1 stop11h 25m

$392

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Thu 10/30

1:20 pm-8:55 am

2 stops14h 35m

$467

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Sat 8/30

5:17 pm-11:07 pm

3 stops24h 50m

$508

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Fri 9/12

10:57 am-9:51 am

3 stops17h 54m

$565

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Sat 1/10

1:45 pm-8:54 am

2 stops15h 09m

$627

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/13

Best time to book a flight from Maui to Midway

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

Related info for your journey

Find useful and relevant information for your journey from Maui to Midway. 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 Maui to Midway that include hotel bookings?

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

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

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

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

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

    Currently, April is the cheapest month in which you can book a flight from Maui to Chicago Midway Airport (average of $160). Flying from Maui to Chicago Midway Airport in November is currently the most expensive (average of $249). 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

Traveling to a place near Chicago Midway Airport?

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

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