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$214+ 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 2/22. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — OGG
Feb 20 — Feb 271
Fri 2/20
Fri 2/27
1 adult, Economy
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Cheap 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 January 21, 2026.

This Delta deal was found by Cheapflights users on 1/18. 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 2/166:00 am
MDW
-
OGG
1 stop13h 37m
Delta
Thu 2/261:53 pm
OGG
-
MDW
2 stops15h 01m
Delta
Deal found 1/18$428
This Delta deal was found by Cheapflights users on 1/19. 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 4/149:27 am
MDW
-
OGG
2 stops15h 04m
Delta
Thu 4/2310:15 pm
OGG
-
MDW
2 stops14h 39m
Delta
Deal found 1/19$433
This Delta deal was found by Cheapflights users on 1/18. 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 2/196:00 am
MDW
-
OGG
1 stop13h 37m
Delta
Wed 2/251:53 pm
OGG
-
MDW
2 stops15h 01m
Delta
Deal found 1/18$451
This Southwest deal was found by Cheapflights users on 1/19. 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.
Tue 4/146:45 am
MDW
-
OGG
1 stop10h 50m
Southwest
Thu 4/238:25 pm
OGG
-
MDW
1 stop10h 30m
Southwest
Deal found 1/19$455
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.
Tue 5/129:20 am
MDW
-
OGG
2 stops16h 25m
Delta
Mon 5/1811:30 pm
OGG
-
MDW
2 stops13h 35m
Delta
Deal found 1/21$456
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.
Tue 5/126:45 am
MDW
-
OGG
1 stop10h 50m
Southwest
Mon 5/188:55 pm
OGG
-
MDW
1 stop12h 35m
Southwest
Deal found 1/21$473
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.
Sat 5/96:00 am
MDW
-
OGG
2 stops12h 40m
Southwest
Fri 5/1510:00 am
OGG
-
MDW
1 stop15h 00m
Southwest
Deal found 1/20$481
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/149:27 am
MDW
-
OGG
2 stops15h 04m
Delta
Tue 4/2112:40 pm
OGG
-
MDW
2 stops15h 07m
Delta
Deal found 1/20$484
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/99:20 am
MDW
-
OGG
2 stops16h 25m
Delta
Fri 5/1511:30 pm
OGG
-
MDW
2 stops14h 01m
Delta
Deal found 1/20$486
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.
Tue 2/248:55 pm
MDW
-
OGG
2 stops20h 15m
Southwest
Mon 3/29:35 pm
OGG
-
MDW
1 stop11h 00m
Southwest
Deal found 1/21$487

Find flight deals from Midway to Maui

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

Most accurate provider

FlightHub
3 stars

Most trusted provider

Expedia
3 stars

Round-trip from

$433
(Delta)

One-way from

$214
(Kiwi.com)

Popular in

December

Cheapest in

October

Average price

$619
Provider with most accurate pricing for Chicago (CHI)-Kahului flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Kahului flights.
Search Deals
From Chicago Midway to Maui
Search Deals
One-way flight from Chicago Midway to Maui
Search Deals
High demand for flights, 0% potential price rise
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($18 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals

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 January 21, 2026.
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

Mon 2/16

6:00 am-3:37 pm

1 stop13h 37m

Kahului

Thu 2/26

1:53 pm-8:54 am

2 stops15h 01m

$428

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Tue 2/24

8:55 pm-1:10 pm

2 stops20h 15m

Kahului

Mon 3/2

9:25 pm-1:10 pm

2 stops11h 45m

$506

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Tue 2/17

1:49 pm-12:28 pm

2 stops26h 39m

Kahului

Wed 2/25

1:53 pm-8:54 am

2 stops15h 01m

$506

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Mon 4/20

6:55 am-2:10 pm

1 stop12h 15m

Kahului

Tue 4/28

10:00 am-6:00 am

1 stop15h 00m

$506

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Mon 2/23

6:00 am-3:37 pm

1 stop13h 37m

Kahului

Sun 3/1

5:10 pm-12:46 pm

2 stops15h 36m

$509

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Mon 2/23

6:00 am-3:37 pm

1 stop13h 37m

Kahului

Tue 3/10

12:59 pm-8:53 am

2 stops14h 54m

$509

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Sun 4/12

6:00 am-3:13 pm

1 stop14h 13m

Kahului

Fri 4/17

10:15 pm-5:54 pm

2 stops14h 39m

$534

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Sun 4/12

6:55 am-2:05 pm

1 stop12h 10m

Kahului

Fri 4/17

8:55 pm-12:20 pm

1 stop10h 25m

$558

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Tue 2/24

8:55 pm-1:10 pm

2 stops20h 15m

Kahului

Tue 3/10

10:00 am-5:00 am

2 stops14h 00m

$582

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Sun 2/22

3:21 pm-2:40 pm

3 stops51h 19m

$214

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/19

Showing 1-10 of 17 results
1
2

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 January 21, 2026.
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
4,266 reviews

Crew

8.6

Food

7.0

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
8.0
Very good
4,266 reviews
Southwest
8.0
Very good
4,266 reviews

Crew

8.6

Food

7.0

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

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 13h 37m. Delta provides one of the quickest options available for as low as $428. 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 January 21, 2026.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$630Average$828FlexibilityNo cancel feeOn-time63%

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