$259+ 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 9/15. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — HNL
Jun 15 — Jun 221
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 May 16, 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 May 16, 2026.
This Southwest deal was found by Cheapflights users on 5/14. 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 10/2110:00 am
MDW
- LIH
1 stop11h 10m
Southwest
Thu 10/298:30 pm
LIH
- MDW
1 stop11h 45m
Southwest
Deal found 5/14![Southwest logo]()
$540
This Southwest deal was found by Cheapflights users on 5/13. 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 8/186:50 am
MDW
- KOA
1 stop10h 50m
Southwest
Tue 8/2510:00 am
KOA
- MDW
1 stop14h 45m
Southwest
Deal found 5/13![Southwest logo]()
$544
This Delta deal was found by Cheapflights users on 5/15. 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 39m
Delta
Thu 8/279:55 pm
LIH
- MDW
2 stops15h 38m
Delta
Deal found 5/15![Delta logo]()
$545
This Delta deal was found by Cheapflights users on 5/15. 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 8/189:59 am
MDW
- KOA
2 stops14h 18m
Delta
Tue 8/259:55 pm
KOA
- MDW
2 stops19h 41m
Delta
Deal found 5/15![Delta logo]()
$546
This Southwest deal was found by Cheapflights users on 5/15. 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 8/186:50 am
MDW
- OGG
1 stop10h 45m
Southwest
Tue 9/2210:00 am
OGG
- MDW
1 stop14h 55m
Southwest
Deal found 5/15![Southwest logo]()
$554
This Southwest deal was found by Cheapflights users on 5/15. 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 10/610:00 am
MDW
- LIH
1 stop11h 10m
Southwest
Tue 10/139:30 pm
LIH
- MDW
1 stop10h 10m
Southwest
Deal found 5/15![Southwest logo]()
$554
This Delta deal was found by Cheapflights users on 5/15. 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 11/29:30 am
MDW
- LIH
2 stops14h 52m
Delta
Mon 11/910:26 pm
LIH
- MDW
2 stops16h 11m
Delta
Deal found 5/15![Delta logo]()
$557
This Southwest deal was found by Cheapflights users on 5/12. 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 9/166:50 am
MDW
- OGG
2 stops14h 20m
Southwest
Wed 9/308:35 pm
OGG
- MDW
1 stop11h 40m
Southwest
Deal found 5/12![Southwest logo]()
$560
This Southwest deal was found by Cheapflights users on 5/12. 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 9/296:50 am
MDW
- LIH
2 stops14h 20m
Southwest
Mon 10/58:30 pm
LIH
- MDW
1 stop12h 05m
Southwest
Deal found 5/12![Southwest logo]()
$561
This Delta deal was found by Cheapflights users on 5/15. 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 9/149:20 am
MDW
- KOA
2 stops14h 14m
Delta
Mon 9/288:40 pm
KOA
- MDW
2 stops16h 25m
Delta
Deal found 5/15![Delta logo]()
$561
This Delta deal was found by Cheapflights users on 5/12. 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 9/299:20 am
MDW
- KOA
2 stops14h 14m
Delta
Fri 10/28:40 pm
KOA
- MDW
2 stops16h 25m
Delta
Deal found 5/12![Delta logo]()
$565
This Southwest deal was found by Cheapflights users on 5/14. 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 8/225:40 am
MDW
- LIH
2 stops17h 25m
Southwest
Thu 8/278:25 pm
LIH
- MDW
2 stops14h 50m
Southwest
Deal found 5/14![Southwest logo]()
$566
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 May 16, 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 May 16, 2026.
This Delta deal was found by Cheapflights users on 5/15. 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 11/29:30 am
MDW
- LIH
2 stops14h 52m
Delta
Mon 11/910:26 pm
LIH
- MDW
2 stops16h 11m
Delta
Deal found 5/15![Delta logo]()
$557
This Southwest deal was found by Cheapflights users on 5/12. 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 9/166:50 am
MDW
- OGG
2 stops14h 20m
Southwest
Wed 9/308:35 pm
OGG
- MDW
1 stop11h 40m
Southwest
Deal found 5/12![Southwest logo]()
$560
This Delta deal was found by Cheapflights users on 5/15. 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 9/219:30 am
MDW
- LIH
2 stops14h 50m
Delta
Tue 9/299:45 pm
LIH
- MDW
2 stops15h 20m
Delta
Deal found 5/15![Delta logo]()
$625
This Southwest deal was found by Cheapflights users on 5/11. 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 11/310:05 am
MDW
- LIH
2 stops15h 25m
Southwest
Tue 11/109:05 pm
LIH
- MDW
1 stop11h 00m
Southwest
Deal found 5/11![Southwest logo]()
$635
This Delta deal was found by Cheapflights users on 5/13. 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 39m
Delta
Thu 8/279:55 pm
LIH
- MDW
2 stops15h 38m
Delta
Deal found 5/13![Delta logo]()
$625
This Southwest deal was found by Cheapflights users on 5/14. 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 9/186:40 am
MDW
- KOA
2 stops16h 25m
Southwest
Wed 9/3010:00 am
KOA
- MDW
2 stops14h 45m
Southwest
Deal found 5/14![Southwest logo]()
$635
This Delta deal was found by Cheapflights users on 5/15. 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 5/299:22 am
MDW
- OGG
2 stops15h 13m
Delta
Mon 6/89:13 pm
OGG
- MDW
2 stops16h 18m
Delta
Deal found 5/15![Delta logo]()
$638
This Southwest deal was found by Cheapflights users on 5/13. 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 10/612:25 pm
MDW
- HNL
2 stops13h 55m
Southwest
Mon 10/129:25 pm
HNL
- MDW
2 stops13h 20m
Southwest
Deal found 5/13![Southwest logo]()
$655
This Delta deal was found by Cheapflights users on 5/15. 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 9/149:20 am
MDW
- KOA
2 stops14h 14m
Delta
Tue 9/298:40 pm
KOA
- MDW
2 stops16h 25m
Delta
Deal found 5/15![Delta logo]()
$640
This Southwest deal was found by Cheapflights users on 5/14. 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 8/106:40 am
MDW
- KOA
1 stop11h 00m
Southwest
Thu 8/2010:00 am
KOA
- MDW
1 stop14h 45m
Southwest
Deal found 5/14![Southwest logo]()
$680
This Delta deal was found by Cheapflights users on 5/15. 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 9/139:20 am
MDW
- KOA
2 stops14h 14m
Delta
Mon 9/288:40 pm
KOA
- MDW
2 stops16h 25m
Delta
Deal found 5/15![Delta logo]()
$656
This Southwest deal was found by Cheapflights users on 5/16. 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 11/115:45 am
MDW
- LIH
2 stops16h 20m
Southwest
Sun 11/159:05 pm
LIH
- MDW
2 stops13h 50m
Southwest
Deal found 5/16![Southwest logo]()
$687
This Delta deal was found by Cheapflights users on 5/11. 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.
Fri 8/219:59 am
MDW
- KOA
2 stops14h 18m
Delta
Fri 8/289:55 pm
KOA
- MDW
2 stops19h 41m
Delta
Deal found 5/11![Delta logo]()
$677
This Southwest deal was found by Cheapflights users on 5/15. 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 8/175:40 am
MDW
- KOA
2 stops13h 30m
Southwest
Sat 8/299:45 am
KOA
- MDW
1 stop15h 00m
Southwest
Deal found 5/15![Southwest logo]()
$721
This Delta deal was found by Cheapflights users on 5/15. 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 9/149:20 am
MDW
- KOA
2 stops14h 14m
Delta
Sun 9/279:45 pm
KOA
- MDW
2 stops15h 46m
Delta
Deal found 5/15![Delta logo]()
$690
This Southwest deal was found by Cheapflights users on 5/11. 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.
Sat 9/51:15 pm
MDW
- HNL
1 stop12h 55m
Southwest
Tue 9/88:55 pm
HNL
- MDW
1 stop10h 00m
Southwest
Deal found 5/11![Southwest logo]()
$734
This Delta deal was found by Cheapflights users on 5/11. 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 7/149:19 am
MDW
- KOA
2 stops14h 58m
Delta
Tue 7/219:55 pm
KOA
- MDW
2 stops15h 30m
Delta
Deal found 5/11![Delta logo]()
$740
This Southwest deal was found by Cheapflights users on 5/15. 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 8/610:15 am
MDW
- OGG
1 stop10h 55m
Southwest
Thu 8/138:55 pm
OGG
- MDW
1 stop10h 50m
Southwest
Deal found 5/15![Southwest logo]()
$745
This Delta deal was found by Cheapflights users on 5/15. 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 6/239:13 pm
OGG
- MDW
2 stops16h 18m
Delta
Deal found 5/15![Delta logo]()
$756
This Southwest deal was found by Cheapflights users on 5/15. 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 7/65:10 am
MDW
- KOA
2 stops14h 00m
Southwest
Mon 7/138:25 pm
KOA
- MDW
1 stop9h 55m
Southwest
Deal found 5/15![Southwest logo]()
$756
This Delta deal was found by Cheapflights users on 5/15. 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 8/36:05 am
MDW
- HNL
1 stop12h 10m
Delta
Mon 8/104:10 pm
HNL
- MDW
2 stops15h 29m
Delta
Deal found 5/15![Delta logo]()
$762
This Southwest deal was found by Cheapflights users on 5/15. 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
2 stops15h 30m
Southwest
Sat 11/1411:20 pm
OGG
- MDW
1 stop14h 20m
Southwest
Deal found 5/15![Southwest logo]()
$771
This Delta deal was found by Cheapflights users on 5/15. 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 10/16:00 am
MDW
- HNL
1 stop12h 15m
Delta
Thu 10/81:30 pm
HNL
- MDW
2 stops14h 19m
Delta
Deal found 5/15![Delta logo]()
$773
This Southwest deal was found by Cheapflights users on 5/11. 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 10/206:10 am
MDW
- ITO
2 stops17h 00m
Southwest
Mon 11/29:25 pm
ITO
- MDW
1 stop10h 40m
Southwest
Deal found 5/11![Southwest logo]()
$776
This Southwest deal was found by Cheapflights users on 5/11. 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.
Mon 6/810:10 am
MDW
- OGG
1 stop11h 00m
Southwest
Mon 6/158:25 pm
OGG
- MDW
1 stop9h 55m
Southwest
Deal found 5/11![Southwest logo]()
$779
This Delta deal was found by Cheapflights users on 5/15. 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 9/159:30 am
MDW
- LIH
2 stops14h 50m
Delta
Tue 9/299:45 pm
LIH
- MDW
2 stops15h 20m
Delta
Deal found 5/15![Delta logo]()
$805
This Southwest deal was found by Cheapflights users on 5/11. 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.
Sat 9/126:55 am
MDW
- OGG
2 stops14h 15m
Southwest
Sat 9/199:10 am
OGG
- MDW
2 stops15h 45m
Southwest
Deal found 5/11![Southwest logo]()
$790
This Delta deal was found by Cheapflights users on 5/14. 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 5/279:23 am
MDW
- OGG
2 stops15h 12m
Delta
Tue 6/28:00 pm
OGG
- MDW
2 stops15h 12m
Delta
Deal found 5/14![Delta logo]()
$811
This Southwest deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/306:55 am
MDW
- OGG
2 stops14h 10m
Southwest
Sat 6/68:25 pm
OGG
- MDW
2 stops13h 15m
Southwest
Deal found 5/14![Southwest logo]()
$791
This Delta deal was found by Cheapflights users on 5/15. 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 8/216:05 am
MDW
- HNL
1 stop12h 10m
Delta
Fri 8/282:45 pm
HNL
- MDW
1 stop13h 32m
Delta
Deal found 5/15![Delta logo]()
$870
Last-minute flights from Midway to HawaiiDiscover last-minute flight deals from Midway to Hawaii. Data last updated May 16, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Hawaii. Data last updated May 16, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/165:10 am
MDW
- OGG
1 stop12h 45m
Southwest
Tue 5/198:35 pm
OGG
- MDW
1 stop12h 35m
Southwest
Deal found 5/12![Southwest logo]()
$674
This Delta deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/169:22 am
MDW
- OGG
2 stops15h 13m
Delta
Tue 5/1910:00 pm
OGG
- MDW
2 stops15h 33m
Delta
Deal found 5/12![Delta logo]()
$685
This Southwest deal was found by Cheapflights users on 5/12. 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 5/2810:05 am
MDW
- OGG
1 stop11h 00m
Southwest
Thu 6/48:55 pm
OGG
- MDW
1 stop10h 40m
Southwest
Deal found 5/12![Southwest logo]()
$577
This Delta deal was found by Cheapflights users on 5/12. 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 5/289:22 am
MDW
- OGG
2 stops15h 13m
Delta
Tue 6/212:55 pm
OGG
- MDW
2 stops14h 47m
Delta
Deal found 5/12![Delta logo]()
$588
This Southwest deal was found by Cheapflights users on 5/12. 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 5/2810:10 am
MDW
- HNL
1 stop15h 55m
Southwest
Mon 6/111:55 am
HNL
- MDW
1 stop12h 30m
Southwest
Deal found 5/12![Southwest logo]()
$620
This Delta deal was found by Cheapflights users on 5/15. 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 5/299:22 am
MDW
- OGG
2 stops15h 13m
Delta
Mon 6/89:13 pm
OGG
- MDW
2 stops16h 18m
Delta
Deal found 5/15![Delta logo]()
$638
This Southwest deal was found by Cheapflights users on 5/11. 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.
Fri 5/2910:05 am
MDW
- OGG
1 stop11h 00m
Southwest
Mon 6/812:35 pm
OGG
- MDW
1 stop11h 25m
Southwest
Deal found 5/11![Southwest logo]()
$640
This Delta deal was found by Cheapflights users on 5/13. 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 6/29:23 am
MDW
- LIH
2 stops13h 17m
Delta
Tue 6/99:55 pm
LIH
- MDW
2 stops15h 36m
Delta
Deal found 5/13![Delta logo]()
$675
This Delta deal was found by Cheapflights users on 5/12. 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 6/29:23 am
MDW
- KOA
2 stops14h 57m
Delta
Sun 6/148:50 pm
KOA
- MDW
2 stops16h 41m
Delta
Deal found 5/12![Delta logo]()
$683
This Delta deal was found by Cheapflights users on 5/15. 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 6/39:23 am
MDW
- KOA
2 stops14h 57m
Delta
Tue 6/98:50 pm
KOA
- MDW
2 stops16h 41m
Delta
Deal found 5/15![Delta logo]()
$648
This Southwest deal was found by Cheapflights users on 5/12. 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 6/310:20 am
MDW
- HNL
1 stop12h 20m
Southwest
Mon 6/812:15 pm
HNL
- MDW
1 stop12h 25m
Southwest
Deal found 5/12![Southwest logo]()
$679
This Southwest deal was found by Cheapflights users on 5/16. 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 6/68:35 pm
MDW
- KOA
1 stop18h 00m
Southwest
Thu 6/1110:00 am
KOA
- MDW
1 stop14h 45m
Southwest
Deal found 5/16![Southwest logo]()
$670
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 May 16, 2026.
Search for one-way flight options from Midway to Hawaii. Find affordable one-way fares based on user searches. Data last updated May 16, 2026.
This Southwest deal was found by Cheapflights users on 5/13. 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 9/156:50 am
MDW
- LIH
2 stops14h 20m
Southwest
Deal found 5/13![Southwest logo]()
$259
This Southwest deal was found by Cheapflights users on 5/11. 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.
Sat 8/226:55 am
MDW
- LIH
2 stops14h 15m
Southwest
Deal found 5/11![Southwest logo]()
$268
This Southwest deal was found by Cheapflights users on 5/11. 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 9/1512:20 pm
MDW
- HNL
1 stop13h 55m
Southwest
Deal found 5/11![Southwest logo]()
$277
This Delta deal was found by Cheapflights users on 5/11. 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 9/159:20 am
MDW
- KOA
2 stops14h 14m
Delta
Deal found 5/11![Delta logo]()
$283
This Southwest deal was found by Cheapflights users on 5/11. 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 9/308:50 pm
MDW
- ITO
2 stops20h 50m
Southwest
Deal found 5/11![Southwest logo]()
$288
This Southwest deal was found by Cheapflights users on 5/14. 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 8/216:40 am
MDW
- LIH
1 stop10h 55m
Southwest
Deal found 5/14![Southwest logo]()
$292
This Southwest deal was found by Cheapflights users on 5/11. 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.
Mon 10/55:50 am
MDW
- ITO
1 stop11h 50m
Southwest
Deal found 5/11![Southwest logo]()
$307
This Southwest deal was found by Cheapflights users on 5/13. 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 10/199:40 am
MDW
- HNL
1 stop16h 30m
Southwest
Deal found 5/13![Southwest logo]()
$307
This Southwest deal was found by Cheapflights users on 5/13. 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 8/1911:10 am
MDW
- HNL
2 stops15h 05m
Southwest
Deal found 5/13![Southwest logo]()
$313
This Southwest deal was found by Cheapflights users on 5/15. 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 9/1710:15 am
MDW
- HNL
1 stop15h 55m
Southwest
Deal found 5/15![Southwest logo]()
$315
This Delta deal was found by Cheapflights users on 5/12. 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 8/299:24 am
MDW
- HNL
2 stops16h 56m
Delta
Deal found 5/12![Delta logo]()
$317
This Southwest deal was found by Cheapflights users on 5/14. 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 10/257:05 am
MDW
- HNL
1 stop11h 05m
Southwest
Deal found 5/14![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 May 16, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $544 (Southwest) |
One-way from | $259 (Southwest) |
Popular in | June |
Cheapest in | January |
Average price | $801 |
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 May 16, 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
Mon 11/2
9:30 am-8:22 pm
2 stops14h 52m
Lihue
Mon 11/9
10:26 pm-6:37 pm
2 stops16h 11m
$557
ChicagoKahului
MDW - OGG
MDWOGG
Chicago Midway
Wed 9/16
6:50 am-4:10 pm
2 stops14h 20m
Kahului
Wed 9/30
8:35 pm-1:15 pm
1 stop11h 40m
$560
ChicagoLihue
MDW - LIH
MDWLIH
Chicago Midway
Mon 9/21
9:30 am-7:20 pm
2 stops14h 50m
Lihue
Tue 9/29
9:45 pm-6:05 pm
2 stops15h 20m
$625
ChicagoLihue
MDW - LIH
MDWLIH
Chicago Midway
Tue 8/18
9:24 am-7:03 pm
2 stops14h 39m
Lihue
Thu 8/27
9:55 pm-6:33 pm
2 stops15h 38m
$625
ChicagoLihue
MDW - LIH
MDWLIH
Chicago Midway
Tue 11/3
10:05 am-9:30 pm
2 stops15h 25m
Lihue
Tue 11/10
9:05 pm-12:05 pm
1 stop11h 00m
$635
ChicagoKailua-Kona
MDW - KOA
MDWKOA
Chicago Midway
Fri 9/18
6:40 am-6:05 pm
2 stops16h 25m
Kona Intl
Wed 9/30
10:00 am-5:45 am
2 stops14h 45m
$635
ChicagoKahului
MDW - OGG
MDWOGG
Chicago Midway
Fri 5/29
9:22 am-7:35 pm
2 stops15h 13m
Kahului
Mon 6/8
9:13 pm-6:31 pm
2 stops16h 18m
$638
ChicagoKailua-Kona
MDW - KOA
MDWKOA
Chicago Midway
Mon 9/14
9:20 am-6:34 pm
2 stops14h 14m
Kona Intl
Tue 9/29
8:40 pm-6:05 pm
2 stops16h 25m
$640
ChicagoHonolulu
MDW - HNL
MDWHNL
Chicago Midway
Tue 10/6
12:25 pm-9:20 pm
2 stops13h 55m
Honolulu
Mon 10/12
9:25 pm-3:45 pm
2 stops13h 20m
$655
ChicagoKailua-Kona
MDW - KOA
MDWKOA
Chicago Midway
Sun 9/13
9:20 am-6:34 pm
2 stops14h 14m
Kona Intl
Mon 9/28
8:40 pm-6:05 pm
2 stops16h 25m
$656
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-LIH
MDW-HNL
MDW-KOA
MDW-ITO
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 Hawaii
MDW-USHI
MDW-LIH
MDW-HNL
MDW-KOA
MDW-ITO
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 May 16, 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.
Entertainment
7.5
Food
7.0
Crew
8.6
Boarding
8.1
Comfort
8.0
Overall
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Food
7.0
Crew
8.6
Boarding
8.1
Comfort
8.0
Overall
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Food
7.0
Crew
8.6
Boarding
8.1
Comfort
8.0
Overall
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
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 May 16, 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 May 16, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$429 | Average$733 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$553 | Average$794 | FlexibilityNo cancel fee | On-time63% |