$236+ 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 9/11. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — HNL
Jul 30 — Aug 61
Round-trip
1 adult, Economy
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Find cheap flights from Midway to Hawaii with Cheapflights
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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 June 30, 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 June 30, 2026.
This Delta deal was found by Cheapflights users on 6/29. 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.
Thu 11/59:29 am
MDW
- LIH
2 stops14h 45m
Delta
Wed 11/1110:26 pm
LIH
- MDW
2 stops14h 24m
Delta
Deal found 6/29![Delta logo]()
$435
This Delta deal was found by Cheapflights users on 6/29. 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 10/289:29 am
MDW
- LIH
2 stops14h 45m
Delta
Sun 11/18:39 pm
LIH
- MDW
2 stops16h 00m
Delta
Deal found 6/29![Delta logo]()
$459
This Delta deal was found by Cheapflights users on 6/25. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/69:24 am
MDW
- LIH
2 stops14h 52m
Delta
Mon 9/149:54 pm
LIH
- MDW
2 stops15h 39m
Delta
Deal found 6/25![Delta logo]()
$463
This Southwest deal was found by Cheapflights users on 6/25. 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.
Tue 8/1810:15 am
MDW
- LIH
1 stop10h 55m
Southwest
Mon 8/248:25 pm
LIH
- MDW
1 stop10h 30m
Southwest
Deal found 6/25![Southwest logo]()
$469
This Southwest deal was found by Cheapflights users on 6/29. 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 10/2010:00 am
MDW
- LIH
1 stop11h 10m
Southwest
Mon 10/269:30 pm
LIH
- MDW
1 stop10h 10m
Southwest
Deal found 6/29![Southwest logo]()
$522
This Delta deal was found by Cheapflights users on 6/25. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/59:59 am
MDW
- LIH
2 stops38h 17m
Delta
Mon 9/148:35 pm
LIH
- MDW
2 stops16h 44m
Delta
Deal found 6/25![Delta logo]()
$524
This Southwest deal was found by Cheapflights users on 6/29. 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 9/146:15 am
MDW
- LIH
2 stops13h 00m
Southwest
Mon 9/218:25 pm
LIH
- MDW
1 stop12h 05m
Southwest
Deal found 6/29![Southwest logo]()
$528
This Southwest deal was found by Cheapflights users on 6/29. 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.
Wed 8/198:20 pm
MDW
- LIH
2 stops24h 50m
Southwest
Tue 8/258:25 pm
LIH
- MDW
1 stop12h 05m
Southwest
Deal found 6/29![Southwest logo]()
$530
This Southwest deal was found by Cheapflights users on 6/28. 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 8/268:50 pm
MDW
- KOA
2 stops20h 35m
Southwest
Wed 9/910:00 am
KOA
- MDW
1 stop14h 45m
Southwest
Deal found 6/28![Southwest logo]()
$545
This Southwest deal was found by Cheapflights users on 6/27. 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 8/176:40 am
MDW
- ITO
1 stop10h 55m
Southwest
Fri 8/218:45 pm
ITO
- MDW
1 stop12h 25m
Southwest
Deal found 6/27![Southwest logo]()
$554
This Southwest deal was found by Cheapflights users on 6/29. 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 11/95:45 am
MDW
- KOA
1 stop11h 55m
Southwest
Fri 11/139:00 am
KOA
- MDW
1 stop16h 45m
Southwest
Deal found 6/29![Southwest logo]()
$554
This Delta deal was found by Cheapflights users on 6/29. 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.
Sun 11/89:29 am
MDW
- KOA
2 stops15h 00m
Delta
Fri 11/139:40 pm
KOA
- MDW
2 stops15h 10m
Delta
Deal found 6/29![Delta logo]()
$565
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 June 30, 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 June 30, 2026.
This Southwest deal was found by Cheapflights users on 6/27. 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 8/226:55 am
MDW
- LIH
2 stops14h 15m
Southwest
Wed 8/268:25 pm
LIH
- MDW
1 stop10h 40m
Southwest
Deal found 6/27![Southwest logo]()
$542
This Delta deal was found by Cheapflights users on 6/25. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/189:24 am
MDW
- LIH
2 stops14h 52m
Delta
Thu 8/278:41 pm
LIH
- MDW
2 stops16h 52m
Delta
Deal found 6/25![Delta logo]()
$611
This Southwest deal was found by Cheapflights users on 6/27. 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 8/176:40 am
MDW
- ITO
1 stop10h 55m
Southwest
Fri 8/218:45 pm
ITO
- MDW
2 stops12h 30m
Southwest
Deal found 6/27![Southwest logo]()
$560
This Southwest deal was found by Cheapflights users on 6/26. 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.
Wed 8/128:20 pm
MDW
- LIH
2 stops24h 50m
Southwest
Thu 8/209:25 pm
LIH
- MDW
2 stops13h 45m
Southwest
Deal found 6/26![Southwest logo]()
$560
This Delta deal was found by Cheapflights users on 6/26. 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.
Tue 8/259:59 am
MDW
- KOA
2 stops14h 18m
Delta
Wed 9/28:42 pm
KOA
- MDW
2 stops16h 51m
Delta
Deal found 6/26![Delta logo]()
$625
This Southwest deal was found by Cheapflights users on 6/29. 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.
Wed 8/1910:15 am
MDW
- LIH
1 stop10h 55m
Southwest
Tue 8/258:25 pm
LIH
- MDW
1 stop12h 05m
Southwest
Deal found 6/29![Southwest logo]()
$562
This Delta deal was found by Cheapflights users on 6/27. 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 8/255:10 pm
MDW
- OGG
2 stops23h 07m
Delta
Mon 8/311:10 pm
OGG
- MDW
2 stops23h 51m
Delta
Deal found 6/27![Delta logo]()
$654
This Southwest deal was found by Cheapflights users on 6/26. 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.
Tue 8/256:50 am
MDW
- KOA
1 stop10h 50m
Southwest
Wed 9/210:00 am
KOA
- MDW
1 stop14h 45m
Southwest
Deal found 6/26![Southwest logo]()
$569
This Delta deal was found by Cheapflights users on 6/26. 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.
Sat 9/59:24 am
MDW
- HNL
2 stops16h 56m
Delta
Sun 9/132:50 pm
HNL
- MDW
1 stop13h 17m
Delta
Deal found 6/26![Delta logo]()
$677
This Southwest deal was found by Cheapflights users on 6/28. 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 8/266:50 am
MDW
- KOA
1 stop10h 50m
Southwest
Wed 9/910:00 am
KOA
- MDW
1 stop14h 45m
Southwest
Deal found 6/28![Southwest logo]()
$569
This Delta deal was found by Cheapflights users on 6/25. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/19:24 am
MDW
- HNL
2 stops16h 56m
Delta
Wed 9/912:35 pm
HNL
- MDW
2 stops15h 13m
Delta
Deal found 6/25![Delta logo]()
$679
This Southwest deal was found by Cheapflights users on 6/26. 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.
Thu 8/206:40 am
MDW
- LIH
2 stops12h 30m
Southwest
Sun 8/238:25 pm
LIH
- MDW
1 stop10h 40m
Southwest
Deal found 6/26![Southwest logo]()
$580
This Delta deal was found by Cheapflights users on 6/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/56:00 am
MDW
- HNL
1 stop13h 14m
Delta
Thu 12/105:45 pm
HNL
- MDW
2 stops14h 48m
Delta
Deal found 6/28![Delta logo]()
$691
This Southwest deal was found by Cheapflights users on 6/25. 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.
Fri 9/116:40 am
MDW
- OGG
2 stops14h 30m
Southwest
Thu 9/178:55 pm
OGG
- MDW
1 stop10h 50m
Southwest
Deal found 6/25![Southwest logo]()
$592
This Southwest deal was found by Cheapflights users on 6/25. 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 8/198:35 am
MDW
- OGG
2 stops12h 35m
Southwest
Sat 8/299:10 am
OGG
- MDW
1 stop15h 45m
Southwest
Deal found 6/25![Southwest logo]()
$592
This Delta deal was found by Cheapflights users on 6/26. 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.
Fri 8/219:59 am
MDW
- KOA
2 stops14h 18m
Delta
Fri 8/288:42 pm
KOA
- MDW
2 stops16h 51m
Delta
Deal found 6/26![Delta logo]()
$780
This Southwest deal was found by Cheapflights users on 6/25. 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.
Tue 8/116:50 am
MDW
- KOA
1 stop10h 50m
Southwest
Tue 8/2510:00 am
KOA
- MDW
1 stop14h 45m
Southwest
Deal found 6/25![Southwest logo]()
$594
This Southwest deal was found by Cheapflights users on 6/27. 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 9/146:15 am
MDW
- LIH
2 stops13h 00m
Southwest
Mon 9/218:25 pm
LIH
- MDW
2 stops12h 55m
Southwest
Deal found 6/27![Southwest logo]()
$602
This Southwest deal was found by Cheapflights users on 6/28. 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.
Mon 8/246:40 am
MDW
- OGG
1 stop10h 55m
Southwest
Sat 8/299:10 am
OGG
- MDW
1 stop15h 45m
Southwest
Deal found 6/28![Southwest logo]()
$626
This Southwest deal was found by Cheapflights users on 6/29. 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.
Thu 8/136:15 am
MDW
- OGG
1 stop12h 30m
Southwest
Thu 8/208:25 pm
OGG
- MDW
1 stop9h 55m
Southwest
Deal found 6/29![Southwest logo]()
$644
This Southwest deal was found by Cheapflights users on 6/28. 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.
Mon 8/245:40 am
MDW
- KOA
2 stops17h 25m
Southwest
Sat 8/299:45 am
KOA
- MDW
1 stop15h 00m
Southwest
Deal found 6/28![Southwest logo]()
$655
This Southwest deal was found by Cheapflights users on 6/29. 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.
Thu 8/136:40 am
MDW
- KOA
1 stop11h 00m
Southwest
Thu 8/2010:00 am
KOA
- MDW
1 stop14h 45m
Southwest
Deal found 6/29![Southwest logo]()
$680
This Southwest deal was found by Cheapflights users on 6/29. 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.
Fri 9/2510:15 am
MDW
- HNL
1 stop15h 55m
Southwest
Mon 9/289:25 pm
HNL
- MDW
1 stop14h 10m
Southwest
Deal found 6/29![Southwest logo]()
$685
This Southwest deal was found by Cheapflights users on 6/28. 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 8/146:40 am
MDW
- OGG
1 stop10h 55m
Southwest
Wed 8/198:55 pm
OGG
- MDW
1 stop10h 50m
Southwest
Deal found 6/28![Southwest logo]()
$690
This Southwest deal was found by Cheapflights users on 6/27. 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
1 stop10h 45m
Southwest
Thu 8/208:35 pm
OGG
- MDW
1 stop10h 30m
Southwest
Deal found 6/27![Southwest logo]()
$690
This Southwest deal was found by Cheapflights users on 6/29. 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.
Sat 8/226:55 am
MDW
- OGG
2 stops14h 15m
Southwest
Sat 8/298:55 pm
OGG
- MDW
2 stops12h 30m
Southwest
Deal found 6/29![Southwest logo]()
$709
This Southwest deal was found by Cheapflights users on 6/26. 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.
Fri 9/255:40 am
MDW
- OGG
2 stops14h 10m
Southwest
Sun 10/48:25 pm
OGG
- MDW
1 stop10h 25m
Southwest
Deal found 6/26![Southwest logo]()
$712
This Southwest deal was found by Cheapflights users on 6/29. 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.
Sat 8/295:40 am
MDW
- ITO
2 stops21h 05m
Southwest
Mon 9/78:45 pm
ITO
- MDW
2 stops13h 00m
Southwest
Deal found 6/29![Southwest logo]()
$715
This Southwest deal was found by Cheapflights users on 6/27. 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 10/1410:05 am
MDW
- HNL
1 stop16h 10m
Southwest
Mon 10/198:55 pm
HNL
- MDW
1 stop10h 45m
Southwest
Deal found 6/27![Southwest logo]()
$719
This Southwest deal was found by Cheapflights users on 6/29. 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.
Fri 8/2812:15 pm
MDW
- HNL
2 stops14h 05m
Southwest
Sun 9/611:55 am
HNL
- MDW
1 stop12h 50m
Southwest
Deal found 6/29![Southwest logo]()
$726
Last-minute flights from Midway to HawaiiDiscover last-minute flight deals from Midway to Hawaii. Data last updated June 30, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Hawaii. Data last updated June 30, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 6/29. 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 7/19:17 am
MDW
- LIH
2 stops14h 45m
Delta
Thu 7/168:31 pm
LIH
- MDW
2 stops16h 54m
Delta
Deal found 6/29![Delta logo]()
$715
This Southwest deal was found by Cheapflights users on 6/25. 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.
Fri 7/310:10 am
MDW
- HNL
1 stop16h 10m
Southwest
Thu 7/1612:55 pm
HNL
- MDW
1 stop17h 15m
Southwest
Deal found 6/25![Southwest logo]()
$707
This Southwest deal was found by Cheapflights users on 6/29. 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.
Sat 7/410:35 am
MDW
- HNL
1 stop15h 30m
Southwest
Sat 7/1112:15 pm
HNL
- MDW
1 stop12h 25m
Southwest
Deal found 6/29![Southwest logo]()
$720
This Southwest deal was found by Cheapflights users on 6/26. 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.
Sat 7/412:50 pm
MDW
- HNL
2 stops13h 15m
Southwest
Thu 7/911:00 am
HNL
- MDW
2 stops13h 25m
Southwest
Deal found 6/26![Southwest logo]()
$731
This Southwest deal was found by Cheapflights users on 6/28. 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.
Mon 7/66:30 am
MDW
- LIH
1 stop11h 15m
Southwest
Fri 7/106:15 am
LIH
- MDW
2 stops12h 15m
Southwest
Deal found 6/28![Southwest logo]()
$692
This Southwest deal was found by Cheapflights users on 6/29. 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 7/145:25 am
MDW
- OGG
1 stop12h 15m
Southwest
Wed 7/228:55 pm
OGG
- MDW
1 stop10h 40m
Southwest
Deal found 6/29![Southwest logo]()
$714
This Southwest deal was found by Cheapflights users on 6/28. 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 7/165:10 am
MDW
- HNL
1 stop11h 35m
Southwest
Mon 7/2011:00 am
HNL
- MDW
1 stop13h 00m
Southwest
Deal found 6/28![Southwest logo]()
$741
This Southwest deal was found by Cheapflights users on 6/27. 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 7/172:15 pm
MDW
- HNL
1 stop12h 15m
Southwest
Fri 7/2412:15 pm
HNL
- MDW
1 stop12h 25m
Southwest
Deal found 6/27![Southwest logo]()
$742
This Southwest deal was found by Cheapflights users on 6/29. 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.
Wed 7/225:30 am
MDW
- OGG
2 stops15h 40m
Southwest
Wed 7/298:35 pm
OGG
- MDW
1 stop10h 10m
Southwest
Deal found 6/29![Southwest logo]()
$756
This Southwest deal was found by Cheapflights users on 6/29. 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.
Fri 7/242:15 pm
MDW
- HNL
1 stop12h 15m
Southwest
Tue 7/288:15 am
HNL
- MDW
1 stop15h 45m
Southwest
Deal found 6/29![Southwest logo]()
$739
This Delta deal was found by Cheapflights users on 6/29. 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 7/299:54 am
MDW
- HNL
2 stops16h 28m
Delta
Thu 8/62:50 pm
HNL
- MDW
1 stop13h 27m
Delta
Deal found 6/29![Delta logo]()
$719
This Southwest deal was found by Cheapflights users on 6/30. 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.
Thu 7/305:20 am
MDW
- OGG
1 stop12h 20m
Southwest
Thu 8/68:55 pm
OGG
- MDW
1 stop10h 50m
Southwest
Deal found 6/30![Southwest logo]()
$634
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 June 30, 2026.
Search for one-way flight options from Midway to Hawaii. Find affordable one-way fares based on user searches. Data last updated June 30, 2026.
This Southwest deal was found by Cheapflights users on 6/25. 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.
Fri 9/1110:15 am
MDW
- LIH
1 stop10h 55m
Southwest
Deal found 6/25![Southwest logo]()
$236
This Southwest deal was found by Cheapflights users on 6/25. 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.
Tue 10/2010:30 am
MDW
- HNL
1 stop15h 50m
Southwest
Deal found 6/25![Southwest logo]()
$247
This Southwest deal was found by Cheapflights users on 6/28. 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 9/2910:15 am
MDW
- LIH
1 stop10h 55m
Southwest
Deal found 6/28![Southwest logo]()
$269
This Southwest deal was found by Cheapflights users on 6/26. 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.
Mon 8/316:40 am
MDW
- HNL
1 stop11h 40m
Southwest
Deal found 6/26![Southwest logo]()
$277
This Southwest deal was found by Cheapflights users on 6/28. 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 9/1510:15 am
MDW
- OGG
1 stop10h 55m
Southwest
Deal found 6/28![Southwest logo]()
$277
This Delta deal was found by Cheapflights users on 6/29. 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.
Tue 8/189:24 am
MDW
- HNL
2 stops16h 56m
Delta
Deal found 6/29![Delta logo]()
$290
This Southwest deal was found by Cheapflights users on 6/28. 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.
Sun 10/49:55 am
MDW
- LIH
1 stop11h 15m
Southwest
Deal found 6/28![Southwest logo]()
$293
This Delta deal was found by Cheapflights users on 6/25. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/119:29 am
MDW
- LIH
2 stops14h 41m
Delta
Deal found 6/25![Delta logo]()
$299
This Southwest deal was found by Cheapflights users on 6/28. 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 9/111:00 am
MDW
- HNL
2 stops15h 20m
Southwest
Deal found 6/28![Southwest logo]()
$313
This Delta deal was found by Cheapflights users on 6/29. 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.
Sat 8/229:24 am
MDW
- HNL
2 stops16h 56m
Delta
Deal found 6/29![Delta logo]()
$317
This Southwest deal was found by Cheapflights users on 6/29. 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.
Thu 8/206:40 am
MDW
- OGG
1 stop10h 55m
Southwest
Deal found 6/29![Southwest logo]()
$319
This Southwest deal was found by Cheapflights users on 6/29. 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.
Thu 8/136:40 am
MDW
- LIH
1 stop10h 55m
Southwest
Deal found 6/29![Southwest logo]()
$322
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 June 30, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $435 (Delta) |
One-way from | $236 (Southwest) |
Popular in | June |
Cheapest in | January |
Average price | $965 |
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 June 30, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Hawaii that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoLihue
MDW - LIH
MDWLIH
Chicago Midway
Sat 8/22
6:55 am-4:10 pm
2 stops14h 15m
Lihue
Wed 8/26
8:25 pm-12:05 pm
1 stop10h 40m
$542
ChicagoHilo
MDW - ITO
MDWITO
Chicago Midway
Mon 8/17
6:40 am-12:35 pm
1 stop10h 55m
Hilo Intl
Fri 8/21
8:45 pm-2:15 pm
2 stops12h 30m
$560
ChicagoLihue
MDW - LIH
MDWLIH
Chicago Midway
Wed 8/12
8:20 pm-4:10 pm
2 stops24h 50m
Lihue
Thu 8/20
9:25 pm-4:10 pm
2 stops13h 45m
$560
ChicagoLihue
MDW - LIH
MDWLIH
Chicago Midway
Wed 8/19
10:15 am-4:10 pm
1 stop10h 55m
Lihue
Tue 8/25
8:25 pm-1:30 pm
1 stop12h 05m
$562
ChicagoKailua-Kona
MDW - KOA
MDWKOA
Chicago Midway
Tue 8/25
6:50 am-12:40 pm
1 stop10h 50m
Kona Intl
Wed 9/2
10:00 am-5:45 am
1 stop14h 45m
$569
ChicagoKailua-Kona
MDW - KOA
MDWKOA
Chicago Midway
Wed 8/26
6:50 am-12:40 pm
1 stop10h 50m
Kona Intl
Wed 9/9
10:00 am-5:45 am
1 stop14h 45m
$569
ChicagoLihue
MDW - LIH
MDWLIH
Chicago Midway
Thu 8/20
6:40 am-2:10 pm
2 stops12h 30m
Lihue
Sun 8/23
8:25 pm-12:05 pm
1 stop10h 40m
$580
ChicagoKahului
MDW - OGG
MDWOGG
Chicago Midway
Fri 9/11
6:40 am-4:10 pm
2 stops14h 30m
Kahului
Thu 9/17
8:55 pm-12:45 pm
1 stop10h 50m
$592
ChicagoKahului
MDW - OGG
MDWOGG
Chicago Midway
Wed 8/19
8:35 am-4:10 pm
2 stops12h 35m
Kahului
Sat 8/29
9:10 am-5:55 am
1 stop15h 45m
$592
ChicagoKailua-Kona
MDW - KOA
MDWKOA
Chicago Midway
Tue 8/11
6:50 am-12:40 pm
1 stop10h 50m
Kona Intl
Tue 8/25
10:00 am-5:45 am
1 stop14h 45m
$594
Showing 1-10 of 60 resultsSorted by cheapest first
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-OGG
MDW-LIH
MDW-HNL
MDW-KOA
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-OGG
MDW-LIH
MDW-HNL
MDW-KOA
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 $282). Flying from Chicago Midway Airport to Hawaii in November is currently the most expensive (average of $840). 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.
How much does it cost to fly round-trip from Chicago Midway Airport to Hawaii?
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 June 30, 2026.
Read through reviews of airlines operating flights from Chicago Midway Airport to Hawaii, such as Southwest. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Comfort
8.0
Crew
8.6
Entertainment
7.5
Overall
7.9
Boarding
8.1
Food
7.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Comfort
8.0
Crew
8.6
Entertainment
7.5
Overall
7.9
Boarding
8.1
Food
7.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
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.
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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 June 30, 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 airline flying from Midway to Hawaii
Discover the top airline 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 June 30, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$553 | Average$809 | FlexibilityNo cancel fee | On-time63% |