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$223+ 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 1/5. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — OGG
dic. 26 — ene. 21
vie. 12/26
vie. 1/2
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 noviembre 26, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$425
(Delta)

One-way from

$223
(Delta)

Popular in

March

Cheapest in

October

Average price

$701
Provider with most accurate pricing for Chicago (CHI)-Kahului flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Kahului flights.
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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. 6% potential increase in price ($52 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($18 potential savings vs. average RT price).
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Average for round-trip flights in November 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 noviembre 26, 2025.

This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 12/115:15 amMDW - OGG
1 stop11h 55mSouthwest
jue. 12/259:25 pmOGG - MDW
1 stop13h 10mSouthwest
Deal found 11/26$579
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.
lun. 12/155:15 amMDW - OGG
2 stops14h 50mSouthwest
dom. 12/219:35 pmOGG - MDW
1 stop10h 40mSouthwest
Deal found 11/24$586
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.
sáb. 12/136:46 pmMDW - OGG
2 stops28h 16mDelta
jue. 12/2510:00 pmOGG - MDW
2 stops15h 19mDelta
Deal found 11/26$600
This Southwest deal was found by Cheapflights users on 11/23. 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.
dom. 12/145:30 amMDW - OGG
1 stop11h 35mSouthwest
mié. 12/179:35 pmOGG - MDW
1 stop11h 30mSouthwest
Deal found 11/23$612
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.
sáb. 12/136:46 pmMDW - OGG
2 stops28h 16mDelta
lun. 12/225:05 pmOGG - MDW
1 stop12h 00mDelta
Deal found 11/26$616
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.
sáb. 12/136:46 pmMDW - OGG
2 stops28h 16mDelta
mié. 12/241:40 pmOGG - MDW
2 stops15h 09mDelta
Deal found 11/26$621
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.
sáb. 12/136:46 pmMDW - OGG
2 stops28h 16mDelta
mar. 12/2311:05 pmOGG - MDW
2 stops19h 17mDelta
Deal found 11/26$640
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.
mié. 12/105:25 amMDW - OGG
1 stop11h 40mSouthwest
dom. 12/149:35 pmOGG - MDW
1 stop10h 00mSouthwest
Deal found 11/24$648

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 noviembre 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

lun. 1/19

6:00 am-7:15 pm

2 stops17h 15m

Kahului

lun. 1/26

10:00 pm-6:36 pm

2 stops16h 36m

$435

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

jue. 1/29

5:05 am-12:50 pm

1 stop11h 45m

Kahului

lun. 2/2

9:35 pm-12:35 pm

1 stop11h 00m

$445

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

mié. 1/21

6:00 am-6:04 pm

2 stops16h 04m

Kahului

lun. 1/26

10:00 pm-6:36 pm

2 stops16h 36m

$466

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

lun. 2/23

6:00 am-3:37 pm

1 stop13h 37m

Kahului

mar. 3/10

9:09 pm-5:55 pm

2 stops15h 46m

$479

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

mié. 1/21

6:00 am-6:04 pm

2 stops16h 04m

Kahului

vie. 1/30

2:02 pm-8:52 am

2 stops14h 50m

$504

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

jue. 1/29

5:05 am-12:50 pm

1 stop11h 45m

Kahului

dom. 2/1

9:35 pm-12:35 pm

1 stop11h 00m

$522

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

mié. 1/21

5:05 am-12:50 pm

1 stop11h 45m

Kahului

lun. 1/26

9:25 pm-2:45 pm

1 stop13h 20m

$533

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

jue. 2/19

5:10 am-2:50 pm

2 stops13h 40m

Kahului

mar. 2/24

9:35 pm-2:45 pm

2 stops13h 10m

$553

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

lun. 1/5

6:45 am-3:37 pm

1 stop12h 52m

$223

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

mar. 12/30

6:00 am-3:24 pm

1 stop13h 24m

$252

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/25

Showing 1-10 of 15 results
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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
No data available for this route at this time. Please check back soon.

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 noviembre 26, 2025.
Get a feel of what it's like to fly with Southwest 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
4,254 reviews

Comfort

8.0

Crew

8.6

Overall

8.0

Food

7.0

Entertainment

7.5

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,254 reviews
Southwest
8.0
Very good
4,254 reviews

Comfort

8.0

Crew

8.6

Overall

8.0

Food

7.0

Entertainment

7.5

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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.

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

    A quick flight from Chicago Midway Airport to Maui can take about 11h 45m. Delta provides one of the quickest options available for as low as $445. Airlines will cover a distance of 4184 mi. This flight may include one or multiple stops.

  • 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.

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 noviembre 26, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$597Average$788FlexibilityNo cancel feeOn-time63%

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