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Midway

$240+ 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 5/4. Fares are subject to change and may not be available on all flights or dates of travel.
OGG — MDW
Feb 20 — Feb 271
Fri 2/20
Fri 2/27
1 adult, Economy
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Cheap 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 January 21, 2026.

This Southwest deal was found by Cheapflights users on 1/20. 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 7/2010:00 am
OGG
-
MDW
1 stop15h 00m
Southwest
Tue 8/116:00 am
MDW
-
OGG
1 stop11h 50m
Southwest
Deal found 1/20$664
This Delta deal was found by Cheapflights users on 1/21. 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 2/201:53 pm
OGG
-
MDW
2 stops17h 10m
Delta
Fri 2/276:00 am
MDW
-
OGG
1 stop13h 37m
Delta
Deal found 1/21$705
This Southwest deal was found by Cheapflights users on 1/21. 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 2/69:25 pm
OGG
-
MDW
1 stop10h 30m
Southwest
Sun 2/85:05 am
MDW
-
OGG
1 stop11h 45m
Southwest
Deal found 1/21$714
This Southwest deal was found by Cheapflights users on 1/21. 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 2/67:00 pm
OGG
-
MDW
2 stops12h 55m
Southwest
Mon 2/95:00 am
MDW
-
OGG
2 stops15h 25m
Southwest
Deal found 1/21$725
This Southwest deal was found by Cheapflights users on 1/21. 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 2/209:35 pm
OGG
-
MDW
1 stop11h 55m
Southwest
Fri 2/277:55 am
MDW
-
OGG
1 stop12h 30m
Southwest
Deal found 1/21$726
This Delta deal was found by Cheapflights users on 1/21. 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 2/59:05 pm
OGG
-
MDW
2 stops17h 31m
Delta
Mon 2/96:00 am
MDW
-
OGG
1 stop13h 37m
Delta
Deal found 1/21$849

Find flight deals from Maui to Midway

Keep the following information in mind while searching for Maui to Midway flight deals. Data was last updated January 21, 2026.

Round-trip from

$664
(Southwest)

One-way from

$240
(Delta)
From Maui to Chicago Midway
Search Deals
One-way flight from Maui to Chicago Midway
Search Deals

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 January 21, 2026.
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

Mon 7/20

10:00 am-6:00 am

1 stop15h 00m

Chicago Midway

Tue 8/11

6:50 am-4:10 pm

2 stops14h 20m

$670

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Fri 2/20

1:53 pm-11:03 am

2 stops17h 10m

Chicago Midway

Fri 2/27

6:00 am-3:37 pm

1 stop13h 37m

$705

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Fri 2/6

9:35 pm-11:50 am

1 stop10h 15m

Chicago Midway

Mon 2/9

8:10 am-4:25 pm

1 stop12h 15m

$714

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Fri 2/6

9:25 pm-11:55 am

1 stop10h 30m

Chicago Midway

Sun 2/8

5:05 am-12:50 pm

1 stop11h 45m

$714

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Fri 2/20

9:35 pm-1:30 pm

1 stop11h 55m

Chicago Midway

Fri 2/27

7:55 am-4:25 pm

1 stop12h 30m

$726

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Thu 2/5

9:05 pm-6:36 pm

2 stops17h 31m

Chicago Midway

Mon 2/9

6:00 am-3:37 pm

1 stop13h 37m

$849

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Mon 5/4

8:25 pm-2:00 pm

1 stop12h 35m

$262

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Sun 3/1

5:10 pm-9:54 am

1 stop12h 44m

$292

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Sat 2/28

3:41 pm-11:54 pm

3 stops52h 13m

$305

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Thu 2/5

4:09 pm-8:43 am

3 stops36h 34m

$305

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/21

Showing 1-10 of 13 results
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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 15h. The time it takes to get you to your destination can typically vary by up to 2h 10m. 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.

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
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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