$373+ 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 7/3. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — OGG
Jul 2 — Jul 91
Round-trip
1 adult, Economy
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Find cheap flights from Midway to Maui with Cheapflights
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Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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Cheapest flights from Midway to MauiExplore 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 June 2, 2026.
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 June 2, 2026.
This Southwest deal was found by Cheapflights users on 5/28. 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.
Thu 10/1510:00 am
MDW
- OGG
1 stop11h 10m
Southwest
Thu 10/228:35 pm
OGG
- MDW
2 stops11h 40m
Southwest
Deal found 5/28![Southwest logo]()
$593
This Southwest deal was found by Cheapflights users on 5/28. 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 8/256:50 am
MDW
- OGG
2 stops14h 20m
Southwest
Tue 9/18:55 pm
OGG
- MDW
2 stops12h 25m
Southwest
Deal found 5/28![Southwest logo]()
$595
This Southwest deal was found by Cheapflights users on 5/30. 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.
Sun 8/236:10 am
MDW
- OGG
1 stop12h 35m
Southwest
Thu 8/2710:00 am
OGG
- MDW
1 stop14h 55m
Southwest
Deal found 5/30![Southwest logo]()
$599
This Southwest deal was found by Cheapflights users on 5/31. 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.
Sun 11/15:10 am
MDW
- OGG
1 stop11h 45m
Southwest
Mon 11/29:25 pm
OGG
- MDW
1 stop10h 40m
Southwest
Deal found 5/31![Southwest logo]()
$607
This Delta deal was found by Cheapflights users on 6/1. 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.
Wed 11/186:00 am
MDW
- OGG
1 stop12h 52m
Delta
Mon 11/235:10 pm
OGG
- MDW
1 stop11h 39m
Delta
Deal found 6/1![Delta logo]()
$614
This Southwest deal was found by Cheapflights users on 5/29. 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 8/176:15 am
MDW
- OGG
1 stop12h 30m
Southwest
Mon 8/248:35 pm
OGG
- MDW
1 stop10h 20m
Southwest
Deal found 5/29![Southwest logo]()
$617
This Delta deal was found by Cheapflights users on 6/1. 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.
Wed 11/186:00 am
MDW
- OGG
1 stop12h 52m
Delta
Tue 11/245:10 pm
OGG
- MDW
2 stops15h 23m
Delta
Deal found 6/1![Delta logo]()
$620
This Southwest deal was found by Cheapflights users on 6/1. 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.
Tue 11/175:45 am
MDW
- OGG
2 stops14h 25m
Southwest
Mon 11/239:25 pm
OGG
- MDW
2 stops13h 05m
Southwest
Deal found 6/1![Southwest logo]()
$625
This Southwest deal was found by Cheapflights users on 5/28. 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 8/126:50 am
MDW
- OGG
2 stops14h 20m
Southwest
Wed 8/198:55 pm
OGG
- MDW
1 stop10h 50m
Southwest
Deal found 5/28![Southwest logo]()
$636
Best flights from Midway to MauiDiscover carefully curated flight deals from Midway to Maui that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated June 2, 2026.
Discover carefully curated flight deals from Midway to Maui that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated June 2, 2026.
This Southwest deal was found by Cheapflights users on 5/29. 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 8/176:15 am
MDW
- OGG
1 stop12h 30m
Southwest
Mon 8/248:55 pm
OGG
- MDW
2 stops12h 50m
Southwest
Deal found 5/29![Southwest logo]()
$623
This Delta deal was found by Cheapflights users on 5/29. 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 7/109:19 am
MDW
- OGG
2 stops15h 15m
Delta
Wed 7/229:15 pm
OGG
- MDW
2 stops16h 10m
Delta
Deal found 5/29![Delta logo]()
$745
This Southwest deal was found by Cheapflights users on 5/31. 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 7/37:30 am
MDW
- OGG
2 stops13h 40m
Southwest
Thu 7/98:35 pm
OGG
- MDW
1 stop10h 10m
Southwest
Deal found 5/31![Southwest logo]()
$710
This Delta deal was found by Cheapflights users on 5/31. 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 6/169:54 am
MDW
- OGG
2 stops14h 35m
Delta
Tue 6/239:40 pm
OGG
- MDW
2 stops15h 38m
Delta
Deal found 5/31![Delta logo]()
$806
This Southwest deal was found by Cheapflights users on 6/1. 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.
Tue 7/148:00 am
MDW
- OGG
2 stops13h 10m
Southwest
Thu 7/238:55 pm
OGG
- MDW
1 stop16h 15m
Southwest
Deal found 6/1![Southwest logo]()
$756
This Delta deal was found by Cheapflights users on 6/1. 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.
Tue 6/309:54 am
MDW
- OGG
2 stops14h 35m
Delta
Wed 7/81:19 pm
OGG
- MDW
2 stops14h 18m
Delta
Deal found 6/1![Delta logo]()
$832
This Southwest deal was found by Cheapflights users on 5/31. 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 7/118:00 am
MDW
- OGG
2 stops13h 10m
Southwest
Sat 7/1812:35 pm
OGG
- MDW
1 stop11h 25m
Southwest
Deal found 5/31![Southwest logo]()
$832
This Southwest deal was found by Cheapflights users on 5/28. 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 8/1210:15 am
MDW
- OGG
1 stop10h 55m
Southwest
Sat 8/229:10 am
OGG
- MDW
1 stop15h 45m
Southwest
Deal found 5/28![Southwest logo]()
$836
This Southwest deal was found by Cheapflights users on 5/30. 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 7/275:45 am
MDW
- OGG
1 stop12h 30m
Southwest
Fri 7/318:55 pm
OGG
- MDW
1 stop10h 40m
Southwest
Deal found 5/30![Southwest logo]()
$846
This Southwest deal was found by Cheapflights users on 5/28. 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 7/226:45 am
MDW
- OGG
1 stop10h 55m
Southwest
Mon 7/2710:50 am
OGG
- MDW
1 stop13h 55m
Southwest
Deal found 5/28![Southwest logo]()
$855
Last-minute flights from Midway to MauiDiscover last-minute flight deals from Midway to Maui. Data last updated June 2, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Maui. Data last updated June 2, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 5/31. 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 6/245:35 am
MDW
- OGG
2 stops15h 35m
Southwest
Wed 7/88:25 pm
OGG
- MDW
2 stops12h 00m
Southwest
Deal found 5/31![Southwest logo]()
$725
This Southwest deal was found by Cheapflights users on 5/29. 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.
Sun 6/286:05 am
MDW
- OGG
1 stop12h 00m
Southwest
Sun 7/510:00 am
OGG
- MDW
1 stop15h 00m
Southwest
Deal found 5/29![Southwest logo]()
$749
This Southwest deal was found by Cheapflights users on 5/30. 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 6/297:10 am
MDW
- OGG
2 stops12h 40m
Southwest
Mon 7/610:00 am
OGG
- MDW
1 stop15h 00m
Southwest
Deal found 5/30![Southwest logo]()
$720
This Southwest deal was found by Cheapflights users on 5/29. 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 6/306:45 am
MDW
- OGG
1 stop10h 55m
Southwest
Wed 7/88:35 pm
OGG
- MDW
1 stop10h 10m
Southwest
Deal found 5/29![Southwest logo]()
$704
This Southwest deal was found by Cheapflights users on 5/31. 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 7/310:10 am
MDW
- OGG
1 stop11h 00m
Southwest
Sat 7/1110:50 am
OGG
- MDW
1 stop13h 55m
Southwest
Deal found 5/31![Southwest logo]()
$734
This Southwest deal was found by Cheapflights users on 5/31. 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 7/37:30 am
MDW
- OGG
2 stops13h 40m
Southwest
Thu 7/98:35 pm
OGG
- MDW
2 stops11h 50m
Southwest
Deal found 5/31![Southwest logo]()
$745
This Delta deal was found by Cheapflights users on 5/29. 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.
Wed 7/229:19 am
MDW
- OGG
2 stops15h 15m
Delta
Wed 7/2910:15 pm
OGG
- MDW
2 stops15h 10m
Delta
Deal found 5/29![Delta logo]()
$685
This Delta deal was found by Cheapflights users on 6/1. 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.
Wed 7/299:19 am
MDW
- OGG
2 stops15h 15m
Delta
Thu 8/612:55 pm
OGG
- MDW
2 stops14h 44m
Delta
Deal found 6/1![Delta logo]()
$715
One-way flights from Midway to MauiSearch for one-way flight options from Midway to Maui. Find affordable one-way fares based on user searches. Data last updated June 2, 2026.
Search for one-way flight options from Midway to Maui. Find affordable one-way fares based on user searches. Data last updated June 2, 2026.
This Southwest deal was found by Cheapflights users on 5/28. 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 7/37:30 am
MDW
- OGG
2 stops13h 40m
Southwest
Deal found 5/28![Southwest logo]()
$373
This Southwest deal was found by Cheapflights users on 5/28. 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.
Thu 6/45:45 am
MDW
- OGG
1 stop12h 25m
Southwest
Deal found 5/28![Southwest logo]()
$413
This Southwest deal was found by Cheapflights users on 6/1. 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.
Tue 6/168:00 am
MDW
- OGG
2 stops13h 10m
Southwest
Deal found 6/1![Southwest logo]()
$418
This Southwest deal was found by Cheapflights users on 5/28. 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.
Thu 7/910:10 am
MDW
- OGG
1 stop11h 00m
Southwest
Deal found 5/28![Southwest logo]()
$423
This Southwest deal was found by Cheapflights users on 6/1. 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.
Wed 6/1710:00 am
MDW
- OGG
1 stop11h 10m
Southwest
Deal found 6/1![Southwest logo]()
$433
This Southwest deal was found by Cheapflights users on 5/28. 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 7/86:10 am
MDW
- OGG
1 stop12h 05m
Southwest
Deal found 5/28![Southwest logo]()
$468
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 June 2, 2026.
Round-trip from | $593 (Southwest) |
|---|---|
One-way from | $373 (Southwest) |
Popular in | December |
Cheapest in | October |
Average price | $885 |
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 June 2, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Maui that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoKahului
MDW - OGG
MDWOGG
Chicago Midway
Mon 8/17
6:15 am-1:45 pm
1 stop12h 30m
Kahului
Mon 8/24
8:55 pm-2:45 pm
2 stops12h 50m
$623
ChicagoKahului
MDW - OGG
MDWOGG
Chicago Midway
Fri 7/3
7:30 am-4:10 pm
2 stops13h 40m
Kahului
Thu 7/9
8:35 pm-11:45 am
1 stop10h 10m
$710
ChicagoKahului
MDW - OGG
MDWOGG
Chicago Midway
Fri 7/10
9:19 am-7:34 pm
2 stops15h 15m
Kahului
Wed 7/22
9:15 pm-6:25 pm
2 stops16h 10m
$745
ChicagoKahului
MDW - OGG
MDWOGG
Chicago Midway
Tue 7/14
8:00 am-4:10 pm
2 stops13h 10m
Kahului
Thu 7/23
8:55 pm-6:10 pm
1 stop16h 15m
$756
ChicagoKahului
MDW - OGG
MDWOGG
Chicago Midway
Tue 6/16
9:54 am-7:29 pm
2 stops14h 35m
Kahului
Tue 6/23
9:40 pm-6:18 pm
2 stops15h 38m
$806
ChicagoKahului
MDW - OGG
MDWOGG
Chicago Midway
Tue 6/30
9:54 am-7:29 pm
2 stops14h 35m
Kahului
Wed 7/8
1:19 pm-8:37 am
2 stops14h 18m
$832
ChicagoKahului
MDW - OGG
MDWOGG
Chicago Midway
Sat 7/11
8:00 am-4:10 pm
2 stops13h 10m
Kahului
Sat 7/18
12:35 pm-5:00 am
1 stop11h 25m
$832
ChicagoKahului
MDW - OGG
MDWOGG
Chicago Midway
Wed 8/12
10:15 am-4:10 pm
1 stop10h 55m
Kahului
Sat 8/22
9:10 am-5:55 am
1 stop15h 45m
$836
Quickest round-trip
ChicagoKahului
MDW - OGG
MDWOGG
Chicago Midway
Mon 7/27
5:45 am-1:15 pm
1 stop12h 30m
Kahului
Fri 7/31
8:55 pm-12:35 pm
1 stop10h 40m
$846
ChicagoKahului
MDW - OGG
MDWOGG
Chicago Midway
Wed 7/22
6:45 am-12:40 pm
1 stop10h 55m
Kahului
Mon 7/27
10:50 am-5:45 am
1 stop13h 55m
$855
Showing 1-10 of 17 resultsSorted by cheapest first
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.
MDW-OGG
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
MDW-zzFUK
MDW-OGG
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 June 2, 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.
Boarding
8.1
Crew
8.6
Entertainment
7.5
Food
7.0
Overall
8.0
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentWalter,May 2026
LAS - BUR
Boarding
8.1
Crew
8.6
Entertainment
7.5
Food
7.0
Overall
8.0
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentWalter,May 2026
LAS - BUR
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.
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Complete your trip
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Midway and Maui flights
Browse other Midway and Maui flight options. Last updated on June 2, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
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 June 2, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$819 | Average$874 | FlexibilityNo cancel fee | On-time63% |