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$211+ 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 11/19. Fares are subject to change and may not be available on all flights or dates of travel.
OGG — MDW
Nov 1 — Nov 81
Sat 11/1
Sat 11/8
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 October 2, 2025.

Round-trip from

$737
(Southwest)

One-way from

$211
(Southwest)
From Maui to Chicago Midway
Search Deals
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 October 2, 2025.

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.
Sat 11/17:50 pmOGG - MDW
1 stop10h 45mSouthwest
Sat 11/85:55 amMDW - OGG
1 stop11h 30mSouthwest
Deal found 10/1$737
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.
Thu 10/1612:25 pmOGG - MDW
2 stops15h 15mDelta
Mon 10/206:00 amMDW - OGG
2 stops17h 18mDelta
Deal found 10/1$939
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/1712:25 pmOGG - MDW
2 stops15h 15mDelta
Tue 10/216:00 amMDW - OGG
2 stops17h 42mDelta
Deal found 10/2$959
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/67:45 pmOGG - MDW
2 stops15h 24mDelta
Mon 10/136:00 amMDW - OGG
2 stops17h 42mDelta
Deal found 10/2$1,332

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 October 2, 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

Sat 11/1

7:50 pm-11:35 am

1 stop10h 45m

Chicago Midway

Sat 11/8

5:55 am-1:25 pm

1 stop11h 30m

$737

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Thu 10/16

12:25 pm-8:40 am

2 stops15h 15m

Chicago Midway

Mon 10/20

6:00 am-6:18 pm

2 stops17h 18m

$939

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Fri 10/17

12:25 pm-8:40 am

2 stops15h 15m

Chicago Midway

Tue 10/21

6:00 am-6:42 pm

2 stops17h 42m

$959

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Wed 11/19

9:25 pm-3:00 pm

1 stop13h 35m

$211

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Thu 11/13

5:10 pm-9:52 am

1 stop12h 42m

$212

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Fri 11/7

1:35 pm-10:30 am

2 stops16h 55m

$217

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Wed 11/19

1:55 pm-9:01 am

2 stops15h 06m

$217

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Fri 1/9

4:09 pm-1:09 pm

2 stops41h 00m

$348

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/1

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.

  • How long is the flight from Maui to Chicago Midway Airport?

    Airlines like Southwest and Delta fly from Maui to Chicago Midway Airport in about 10h 45m. The time it takes to get you to your destination can typically vary by up to 4h 30m. Airlines will cover a distance of 4184 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • 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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