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$193+ 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 2/18. Fares are subject to change and may not be available on all flights or dates of travel.
OGG — MDW
Dec 26 — Jan 21
Fri 12/26
Fri 1/2
1 adult, Economy
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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 November 26, 2025.

This Delta deal was found by Cheapflights users on 11/24. 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 12/185:10 pmOGG - MDW
1 stop12h 44mDelta
Tue 12/306:00 amMDW - OGG
1 stop13h 24mDelta
Deal found 11/24$502
This Delta deal was found by Cheapflights users on 11/24. 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 12/225:05 pmOGG - MDW
1 stop12h 00mDelta
Tue 12/306:00 amMDW - OGG
1 stop13h 24mDelta
Deal found 11/24$543
This Delta deal was found by Cheapflights users on 11/24. 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 12/195:10 pmOGG - MDW
1 stop11h 55mDelta
Tue 12/306:00 amMDW - OGG
1 stop13h 24mDelta
Deal found 11/24$563
This Delta deal was found by Cheapflights users on 11/24. 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.
Sun 12/2111:18 amOGG - MDW
2 stops17h 31mDelta
Tue 12/306:00 amMDW - OGG
1 stop13h 24mDelta
Deal found 11/24$681
This Delta deal was found by Cheapflights users on 11/24. 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.
Sun 12/2111:18 amOGG - MDW
2 stops17h 31mDelta
Wed 12/316:00 amMDW - OGG
1 stop13h 24mDelta
Deal found 11/24$725
This Southwest deal was found by Cheapflights users on 11/25. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/269:35 pmOGG - MDW
1 stop10h 05mSouthwest
Sun 11/3010:55 pmMDW - OGG
1 stop17h 30mSouthwest
Deal found 11/25$763
This Southwest deal was found by Cheapflights users on 11/24. 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 12/199:35 pmOGG - MDW
1 stop12h 05mSouthwest
Sun 12/285:40 amMDW - OGG
2 stops13h 10mSouthwest
Deal found 11/24$856
This Delta deal was found by Cheapflights users on 11/26. 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 12/115:10 pmOGG - MDW
1 stop12h 44mDelta
Mon 12/156:00 amMDW - OGG
1 stop13h 24mDelta
Deal found 11/26$881

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 November 26, 2025.

Round-trip from

$502
(Delta)

One-way from

$193
(Kiwi.com)
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 November 26, 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

Thu 12/18

5:10 pm-9:54 am

1 stop12h 44m

Chicago Midway

Wed 12/31

6:00 am-3:24 pm

1 stop13h 24m

$502

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Mon 3/2

5:10 pm-9:56 am

1 stop12h 46m

Chicago Midway

Wed 3/4

6:00 am-12:28 pm

2 stops34h 28m

$513

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Fri 1/16

9:05 pm-4:29 pm

2 stops15h 24m

Chicago Midway

Tue 1/20

9:32 am-7:15 pm

2 stops13h 43m

$532

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Mon 12/22

5:05 pm-9:05 am

1 stop12h 00m

Chicago Midway

Wed 12/31

6:00 am-3:24 pm

1 stop13h 24m

$543

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Mon 12/22

5:05 pm-9:05 am

1 stop12h 00m

Chicago Midway

Tue 12/30

6:00 am-3:24 pm

1 stop13h 24m

$543

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Sun 12/21

5:10 pm-9:05 am

1 stop11h 55m

Chicago Midway

Tue 12/30

6:00 am-3:24 pm

1 stop13h 24m

$563

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Fri 12/19

5:10 pm-9:05 am

1 stop11h 55m

Chicago Midway

Wed 12/31

6:00 am-3:24 pm

1 stop13h 24m

$563

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Fri 12/19

5:10 pm-9:05 am

1 stop11h 55m

Chicago Midway

Tue 12/30

6:00 am-3:24 pm

1 stop13h 24m

$563

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Tue 1/20

12:32 pm-11:45 am

3 stops43h 13m

$209

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Thu 12/25

9:25 pm-2:35 pm

1 stop13h 10m

$223

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/24

Showing 1-10 of 17 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 Delta fly from Maui to Chicago Midway Airport in about 12h 44m. The time it takes to get you to your destination can typically vary by up to . Airlines will cover a distance of 4184 mi.

  • 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
Hammond
Porter
Benton Harbor
Merrillville

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