$173+ Cheap flights from Midway (MDW) to Hawaii
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 3/2. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — HNL
Mar 13 — Mar 201
1 adult, Economy
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Find cheap flights from Midway to Hawaii with Cheapflights
1. Tell us where you want to go
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Cheapest flights from Midway to HawaiiExplore the most affordable flight options available from Midway to Hawaii. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 11, 2026.
Explore the most affordable flight options available from Midway to Hawaii. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 11, 2026.
This Southwest deal was found by Cheapflights users on 2/9. 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 3/910:15 am
MDW
- HNL
1 stop15h 55m
Southwest
Mon 3/1611:55 am
HNL
- MDW
1 stop13h 00m
Southwest
Deal found 2/9![Southwest logo]()
$401
This Southwest deal was found by Cheapflights users on 2/9. 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 4/2911:45 am
MDW
- HNL
2 stops14h 15m
Southwest
Mon 5/411:55 am
HNL
- MDW
1 stop12h 30m
Southwest
Deal found 2/9![Southwest logo]()
$407
This Southwest deal was found by Cheapflights users on 2/10. 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 4/1410:05 am
MDW
- HNL
1 stop15h 55m
Southwest
Tue 4/211:00 pm
HNL
- MDW
1 stop17h 15m
Southwest
Deal found 2/10![Southwest logo]()
$418
This Southwest deal was found by Cheapflights users on 2/9. 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 4/2810:05 am
MDW
- HNL
1 stop15h 55m
Southwest
Tue 5/511:55 am
HNL
- MDW
2 stops12h 45m
Southwest
Deal found 2/9![Southwest logo]()
$419
This Southwest deal was found by Cheapflights users on 2/11. 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 3/48:10 am
MDW
- HNL
2 stops16h 50m
Southwest
Wed 3/118:15 am
HNL
- MDW
1 stop15h 45m
Southwest
Deal found 2/11![Southwest logo]()
$429
This Delta deal was found by Cheapflights users on 2/9. 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 3/49:34 am
MDW
- HNL
2 stops15h 54m
Delta
Tue 3/103:46 pm
HNL
- MDW
1 stop12h 07m
Delta
Deal found 2/9![Delta logo]()
$430
This Southwest deal was found by Cheapflights users on 2/9. 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 4/195:45 am
MDW
- OGG
2 stops14h 00m
Southwest
Mon 4/2710:00 am
OGG
- MDW
1 stop15h 00m
Southwest
Deal found 2/9![Southwest logo]()
$432
This Southwest deal was found by Cheapflights users on 2/11. 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 5/511:45 am
MDW
- HNL
2 stops14h 20m
Southwest
Wed 5/1311:55 am
HNL
- MDW
2 stops12h 45m
Southwest
Deal found 2/11![Southwest logo]()
$434
This Delta deal was found by Cheapflights users on 2/9. 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 5/109:22 am
MDW
- OGG
2 stops15h 13m
Delta
Mon 5/1810:00 pm
OGG
- MDW
2 stops15h 14m
Delta
Deal found 2/9![Delta logo]()
$436
This Southwest deal was found by Cheapflights users on 2/10. 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 4/269:50 pm
MDW
- HNL
1 stop17h 00m
Southwest
Fri 5/18:15 am
HNL
- MDW
1 stop15h 45m
Southwest
Deal found 2/10![Southwest logo]()
$438
This Delta deal was found by Cheapflights users on 2/11. 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 4/76:00 am
MDW
- OGG
1 stop14h 13m
Delta
Wed 4/1510:30 pm
OGG
- MDW
2 stops14h 28m
Delta
Deal found 2/11![Delta logo]()
$438
This Delta deal was found by Cheapflights users on 2/9. 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 2/249:34 am
MDW
- LIH
2 stops14h 15m
Delta
Tue 3/39:20 pm
LIH
- MDW
2 stops17h 20m
Delta
Deal found 2/9![Delta logo]()
$467
Best flights from Midway to HawaiiDiscover carefully curated flight deals from Midway to Hawaii that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 11, 2026.
Discover carefully curated flight deals from Midway to Hawaii that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 11, 2026.
This Southwest deal was found by Cheapflights users on 2/11. 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 3/48:10 am
MDW
- HNL
2 stops16h 50m
Southwest
Wed 3/118:15 am
HNL
- MDW
1 stop15h 45m
Southwest
Deal found 2/11![Southwest logo]()
$429
This Delta deal was found by Cheapflights users on 2/11. 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 4/76:00 am
MDW
- OGG
1 stop14h 13m
Delta
Wed 4/1510:30 pm
OGG
- MDW
2 stops14h 28m
Delta
Deal found 2/11![Delta logo]()
$438
This Southwest deal was found by Cheapflights users on 2/8. 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 3/38:15 am
MDW
- HNL
1 stop16h 45m
Southwest
Mon 3/98:10 am
HNL
- MDW
1 stop15h 25m
Southwest
Deal found 2/8![Southwest logo]()
$440
This Delta deal was found by Cheapflights users on 2/9. 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 4/99:30 am
MDW
- HNL
2 stops16h 23m
Delta
Thu 4/164:10 pm
HNL
- MDW
2 stops15h 33m
Delta
Deal found 2/9![Delta logo]()
$453
This Southwest deal was found by Cheapflights users on 2/10. 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 3/38:10 am
MDW
- HNL
2 stops16h 50m
Southwest
Tue 3/109:05 pm
HNL
- MDW
2 stops13h 45m
Southwest
Deal found 2/10![Southwest logo]()
$449
This Delta deal was found by Cheapflights users on 2/10. 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 2/249:34 am
MDW
- LIH
2 stops14h 15m
Delta
Tue 3/1010:05 pm
LIH
- MDW
2 stops14h 49m
Delta
Deal found 2/10![Delta logo]()
$475
This Delta deal was found by Cheapflights users on 2/11. 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 3/106:34 pm
MDW
- OGG
2 stops21h 56m
Delta
Tue 3/174:00 pm
OGG
- MDW
1 stop12h 56m
Delta
Deal found 2/11![Delta logo]()
$491
This Southwest deal was found by Cheapflights users on 2/8. 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 3/28:10 am
MDW
- KOA
2 stops17h 10m
Southwest
Wed 3/47:00 pm
KOA
- MDW
2 stops13h 30m
Southwest
Deal found 2/8![Southwest logo]()
$495
This Delta deal was found by Cheapflights users on 2/11. 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 3/106:34 pm
MDW
- OGG
2 stops21h 56m
Delta
Wed 3/1812:59 pm
OGG
- MDW
2 stops14h 51m
Delta
Deal found 2/11![Delta logo]()
$496
This Southwest deal was found by Cheapflights users on 2/10. 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 3/1010:05 am
MDW
- HNL
1 stop15h 55m
Southwest
Tue 3/178:15 am
HNL
- MDW
1 stop15h 45m
Southwest
Deal found 2/10![Southwest logo]()
$503
This Delta deal was found by Cheapflights users on 2/10. 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 3/99:35 am
MDW
- KOA
2 stops14h 02m
Delta
Mon 3/1610:15 pm
KOA
- MDW
2 stops14h 39m
Delta
Deal found 2/10![Delta logo]()
$497
This Southwest deal was found by Cheapflights users on 2/10. 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 4/139:45 pm
MDW
- HNL
1 stop17h 05m
Southwest
Sun 4/198:10 am
HNL
- MDW
1 stop15h 25m
Southwest
Deal found 2/10![Southwest logo]()
$533
This Delta deal was found by Cheapflights users on 2/10. 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 4/161:23 pm
MDW
- HNL
2 stops13h 22m
Delta
Thu 4/233:15 pm
HNL
- MDW
1 stop12h 32m
Delta
Deal found 2/10![Delta logo]()
$500
This Southwest deal was found by Cheapflights users on 2/11. 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 4/129:50 pm
MDW
- HNL
1 stop17h 00m
Southwest
Wed 4/2211:55 am
HNL
- MDW
2 stops12h 45m
Southwest
Deal found 2/11![Southwest logo]()
$538
This Delta deal was found by Cheapflights users on 2/11. 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 4/16:00 am
MDW
- OGG
1 stop14h 13m
Delta
Tue 4/74:45 pm
OGG
- MDW
1 stop14h 17m
Delta
Deal found 2/11![Delta logo]()
$503
This Southwest deal was found by Cheapflights users on 2/8. 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 4/76:10 am
MDW
- KOA
2 stops13h 20m
Southwest
Tue 4/148:25 pm
KOA
- MDW
2 stops12h 50m
Southwest
Deal found 2/8![Southwest logo]()
$538
This Delta deal was found by Cheapflights users on 2/8. 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 2/249:34 am
MDW
- LIH
2 stops14h 15m
Delta
Tue 3/39:20 pm
LIH
- MDW
2 stops17h 20m
Delta
Deal found 2/8![Delta logo]()
$504
This Southwest deal was found by Cheapflights users on 2/10. 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 5/510:10 am
MDW
- HNL
1 stop15h 55m
Southwest
Sun 5/108:50 pm
HNL
- MDW
2 stops12h 30m
Southwest
Deal found 2/10![Southwest logo]()
$539
This Delta deal was found by Cheapflights users on 2/9. 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 2/249:34 am
MDW
- LIH
2 stops14h 15m
Delta
Wed 3/410:40 pm
LIH
- MDW
2 stops14h 57m
Delta
Deal found 2/9![Delta logo]()
$505
This Southwest deal was found by Cheapflights users on 2/9. 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 4/205:10 am
MDW
- OGG
2 stops13h 00m
Southwest
Mon 4/2710:00 am
OGG
- MDW
1 stop15h 00m
Southwest
Deal found 2/9![Southwest logo]()
$540
This Delta deal was found by Cheapflights users on 2/8. 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 4/249:31 am
MDW
- HNL
2 stops17h 14m
Delta
Mon 5/43:15 pm
HNL
- MDW
1 stop12h 32m
Delta
Deal found 2/8![Delta logo]()
$535
This Southwest deal was found by Cheapflights users on 2/10. 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 3/56:05 am
MDW
- OGG
1 stop11h 30m
Southwest
Wed 3/118:55 pm
OGG
- MDW
1 stop10h 50m
Southwest
Deal found 2/10![Southwest logo]()
$545
This Delta deal was found by Cheapflights users on 2/11. 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 5/119:22 am
MDW
- HNL
2 stops16h 49m
Delta
Tue 5/1910:38 pm
HNL
- MDW
2 stops14h 18m
Delta
Deal found 2/11![Delta logo]()
$535
This Southwest deal was found by Cheapflights users on 2/9. 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 4/286:10 am
MDW
- KOA
1 stop12h 05m
Southwest
Thu 5/78:25 pm
KOA
- MDW
1 stop11h 45m
Southwest
Deal found 2/9![Southwest logo]()
$551
This Delta deal was found by Cheapflights users on 2/10. 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 3/56:00 am
MDW
- OGG
1 stop13h 37m
Delta
Tue 3/1012:59 pm
OGG
- MDW
2 stops14h 51m
Delta
Deal found 2/10![Delta logo]()
$549
This Southwest deal was found by Cheapflights users on 2/9. 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 5/115:10 am
MDW
- KOA
2 stops14h 05m
Southwest
Tue 5/1910:00 am
KOA
- MDW
1 stop14h 45m
Southwest
Deal found 2/9![Southwest logo]()
$560
This Southwest deal was found by Cheapflights users on 2/9. 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 5/126:10 am
MDW
- KOA
2 stops16h 55m
Southwest
Tue 5/1910:00 am
KOA
- MDW
1 stop14h 45m
Southwest
Deal found 2/9![Southwest logo]()
$560
This Delta deal was found by Cheapflights users on 2/11. 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 4/147:16 pm
MDW
- OGG
2 stops20h 49m
Delta
Wed 4/2210:30 pm
OGG
- MDW
2 stops15h 06m
Delta
Deal found 2/11![Delta logo]()
$562
This Southwest deal was found by Cheapflights users on 2/10. 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 4/136:35 am
MDW
- OGG
1 stop11h 00m
Southwest
Sun 4/198:55 pm
OGG
- MDW
1 stop10h 40m
Southwest
Deal found 2/10![Southwest logo]()
$568
This Delta deal was found by Cheapflights users on 2/11. 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 5/79:23 am
MDW
- LIH
2 stops13h 17m
Delta
Wed 5/138:31 pm
LIH
- MDW
2 stops16h 43m
Delta
Deal found 2/11![Delta logo]()
$582
Last-minute flights from Midway to HawaiiDiscover last-minute flight deals from Midway to Hawaii. Data last updated February 11, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Hawaii. Data last updated February 11, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 2/9. 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 2/249:34 am
MDW
- LIH
2 stops14h 15m
Delta
Tue 3/39:20 pm
LIH
- MDW
2 stops17h 20m
Delta
Deal found 2/9![Delta logo]()
$467
This Delta deal was found by Cheapflights users on 2/10. 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 2/249:34 am
MDW
- LIH
2 stops14h 15m
Delta
Wed 3/49:20 pm
LIH
- MDW
2 stops16h 17m
Delta
Deal found 2/10![Delta logo]()
$475
This Delta deal was found by Cheapflights users on 2/9. 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 2/249:34 am
MDW
- LIH
2 stops14h 15m
Delta
Tue 3/1010:05 pm
LIH
- MDW
2 stops14h 49m
Delta
Deal found 2/9![Delta logo]()
$485
This Southwest deal was found by Cheapflights users on 2/9. 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 3/28:35 pm
MDW
- HNL
1 stop18h 40m
Southwest
Tue 3/109:05 pm
HNL
- MDW
2 stops13h 45m
Southwest
Deal found 2/9![Southwest logo]()
$444
This Southwest deal was found by Cheapflights users on 2/8. 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 3/28:10 am
MDW
- KOA
2 stops17h 10m
Southwest
Wed 3/47:00 pm
KOA
- MDW
2 stops13h 30m
Southwest
Deal found 2/8![Southwest logo]()
$495
This Southwest deal was found by Cheapflights users on 2/9. 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 3/38:10 am
MDW
- HNL
2 stops16h 50m
Southwest
Tue 3/109:05 pm
HNL
- MDW
2 stops13h 45m
Southwest
Deal found 2/9![Southwest logo]()
$443
This Southwest deal was found by Cheapflights users on 2/8. 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 3/38:10 am
MDW
- HNL
2 stops16h 50m
Southwest
Mon 3/98:10 am
HNL
- MDW
1 stop15h 25m
Southwest
Deal found 2/8![Southwest logo]()
$446
This Southwest deal was found by Cheapflights users on 2/11. 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 3/48:10 am
MDW
- HNL
2 stops16h 50m
Southwest
Wed 3/118:15 am
HNL
- MDW
1 stop15h 45m
Southwest
Deal found 2/11![Southwest logo]()
$429
This Delta deal was found by Cheapflights users on 2/9. 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 3/49:34 am
MDW
- HNL
2 stops15h 54m
Delta
Tue 3/103:46 pm
HNL
- MDW
1 stop12h 07m
Delta
Deal found 2/9![Delta logo]()
$430
This Southwest deal was found by Cheapflights users on 2/9. 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 3/910:15 am
MDW
- HNL
1 stop15h 55m
Southwest
Mon 3/1611:55 am
HNL
- MDW
1 stop13h 00m
Southwest
Deal found 2/9![Southwest logo]()
$401
This Delta deal was found by Cheapflights users on 2/10. 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 3/109:35 am
MDW
- HNL
2 stops16h 18m
Delta
Tue 3/173:46 pm
HNL
- MDW
1 stop12h 07m
Delta
Deal found 2/10![Delta logo]()
$458
This Delta deal was found by Cheapflights users on 2/11. 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 3/106:34 pm
MDW
- OGG
2 stops21h 56m
Delta
Tue 3/174:00 pm
OGG
- MDW
1 stop12h 56m
Delta
Deal found 2/11![Delta logo]()
$491
One-way flights from Midway to HawaiiSearch for one-way flight options from Midway to Hawaii. Find affordable one-way fares based on user searches. Data last updated February 11, 2026.
Search for one-way flight options from Midway to Hawaii. Find affordable one-way fares based on user searches. Data last updated February 11, 2026.
This Kiwi.com deal was found by Cheapflights users on 2/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/27:25 pm
MDW
- KOA
3 stops46h 00m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$173
This Southwest deal was found by Cheapflights users on 2/9. 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 4/276:35 am
MDW
- OGG
1 stop11h 00m
Southwest
Deal found 2/9![Southwest logo]()
$211
This Southwest deal was found by Cheapflights users on 2/9. 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 4/135:10 am
MDW
- LIH
1 stop13h 00m
Southwest
Deal found 2/9![Southwest logo]()
$211
This Southwest deal was found by Cheapflights users on 2/8. 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 5/105:10 am
MDW
- LIH
2 stops16h 00m
Southwest
Deal found 2/8![Southwest logo]()
$217
This Delta deal was found by Cheapflights users on 2/9. 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 4/139:31 am
MDW
- HNL
2 stops17h 14m
Delta
Deal found 2/9![Delta logo]()
$218
This Southwest deal was found by Cheapflights users on 2/9. 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 4/146:10 am
MDW
- OGG
2 stops13h 35m
Southwest
Deal found 2/9![Southwest logo]()
$218
This Kiwi.com deal was found by Cheapflights users on 2/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/26:00 am
MDW
- HNL
3 stops57h 15m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$222
This Southwest deal was found by Cheapflights users on 2/9. 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 5/79:45 pm
MDW
- HNL
1 stop17h 05m
Southwest
Deal found 2/9![Southwest logo]()
$230
This Delta deal was found by Cheapflights users on 2/9. 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 3/179:35 am
MDW
- HNL
2 stops16h 18m
Delta
Deal found 2/9![Delta logo]()
$236
This Kiwi.com deal was found by Cheapflights users on 2/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/13:21 pm
MDW
- KOA
3 stops50h 04m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$236
This Southwest deal was found by Cheapflights users on 2/8. 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 4/146:10 am
MDW
- LIH
1 stop12h 00m
Southwest
Deal found 2/8![Southwest logo]()
$239
This Kiwi.com deal was found by Cheapflights users on 2/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/139:04 pm
MDW
- LIH
3 stops38h 13m
Multiple Airlines
Deal found 2/9![Multiple Airlines logo]()
$240
Find flight deals from Midway to Hawaii
Keep the following information in mind while searching for Midway to Hawaii flight deals. Data was last updated February 11, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $401 (Southwest) |
One-way from | $173 (Kiwi.com) |
Popular in | June |
Cheapest in | January |
Average price | $643 |
Cheapflights Fare Finder
Customize your flight search to find flights from Midway to Hawaii 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 February 11, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Hawaii that are best for you.
Fly from
Midway
Fly to
Hawaii
Route
Depart
Return
Price
ChicagoHonolulu
MDW - HNL
MDWHNL
Chicago Midway
Wed 3/4
8:10 am-9:00 pm
2 stops16h 50m
Honolulu
Wed 3/11
8:15 am-5:00 am
1 stop15h 45m
$429
ChicagoKahului
MDW - OGG
MDWOGG
Chicago Midway
Tue 4/7
6:00 am-3:13 pm
1 stop14h 13m
Kahului
Wed 4/15
10:30 pm-5:58 pm
2 stops14h 28m
$438
ChicagoHonolulu
MDW - HNL
MDWHNL
Chicago Midway
Tue 3/3
8:15 am-9:00 pm
1 stop16h 45m
Honolulu
Mon 3/9
8:10 am-4:35 am
1 stop15h 25m
$440
ChicagoHonolulu
MDW - HNL
MDWHNL
Chicago Midway
Tue 3/3
8:10 am-9:00 pm
2 stops16h 50m
Honolulu
Tue 3/10
9:05 pm-3:50 pm
2 stops13h 45m
$449
ChicagoHonolulu
MDW - HNL
MDWHNL
Chicago Midway
Thu 4/9
9:30 am-8:53 pm
2 stops16h 23m
Honolulu
Thu 4/16
4:10 pm-12:43 pm
2 stops15h 33m
$453
ChicagoLihue
MDW - LIH
MDWLIH
Chicago Midway
Tue 2/24
9:34 am-7:49 pm
2 stops14h 15m
Lihue
Tue 3/10
10:05 pm-5:54 pm
2 stops14h 49m
$475
ChicagoKahului
MDW - OGG
MDWOGG
Chicago Midway
Tue 3/10
6:34 pm-11:30 am
2 stops21h 56m
Kahului
Tue 3/17
4:00 pm-9:56 am
1 stop12h 56m
$491
ChicagoKailua-Kona
MDW - KOA
MDWKOA
Chicago Midway
Mon 3/2
8:10 am-9:20 pm
2 stops17h 10m
Kona Intl
Wed 3/4
7:00 pm-12:30 pm
2 stops13h 30m
$495
ChicagoKahului
MDW - OGG
MDWOGG
Chicago Midway
Tue 3/10
6:34 pm-11:30 am
2 stops21h 56m
Kahului
Wed 3/18
12:59 pm-8:50 am
2 stops14h 51m
$496
ChicagoKailua-Kona
MDW - KOA
MDWKOA
Chicago Midway
Mon 3/9
9:35 am-6:37 pm
2 stops14h 02m
Kona Intl
Mon 3/16
10:15 pm-5:54 pm
2 stops14h 39m
$497
Showing 1-10 of 60 results
Best time to book a flight from Midway to Hawaii
Have a flexible travel schedule? Discover the best time to fly to Hawaii from Midway with our price prediction graph.
MDW-KOA
MDW-OGG
MDW-HNL
MDW-LIH
MDW-ITO
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 Hawaii
MDW-USHI
MDW-KOA
MDW-OGG
MDW-HNL
MDW-LIH
What is the cheapest month to book a flight from Chicago Midway Airport to Hawaii?
Currently, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Hawaii (average of $310). Flying from Chicago Midway Airport to Hawaii in November is currently the most expensive (average of $843). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
Reviews of airlines servicing Hawaii
Get insights into the airlines that provide service to Hawaii. 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 Hawaii. Reviews last updated February 11, 2026.
Read through reviews of airlines operating flights from Chicago Midway Airport to Hawaii, such as Southwest and Delta. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Comfort
8.0
Entertainment
7.5
Food
7.0
Boarding
8.1
Crew
8.6
Overall
8.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Comfort
8.0
Entertainment
7.5
Food
7.0
Boarding
8.1
Crew
8.6
Overall
8.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Comfort
8.0
Entertainment
7.5
Food
7.0
Boarding
8.1
Crew
8.6
Overall
8.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Related info for your journey
Find useful and relevant information for your journey from Midway to Hawaii. 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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Alternative routes for Midway to Hawaii
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Hawaii by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Midway to Hawaii by cabin class
Find flights from Midway to Hawaii, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Midway and Hawaii flights
Browse other Midway and Hawaii flight options. Last updated on February 11, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Midway to Hawaii flights
Consider these flights traveling from Midway to Hawaii.
Top 2 airlines flying from Midway to Hawaii
Discover the top 2 airlines that operate flights from Midway to Hawaii. 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 February 11, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$429 | Average$614 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$468 | Average$816 | FlexibilityNo cancel fee | On-time63% |