$218+ Cheap flights from Midway (MDW) to Hawaii
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 1/17. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — HNL
Dec 14 — Dec 211
Round-trip
1 adult, Economy
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Find cheap flights from Midway to Hawaii with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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Cheapest flights from Midway to 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 November 14, 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 November 14, 2026.
This Southwest deal was found by Cheapflights users on 11/9. 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 12/75:50 am -
1 stop11h 25m
Mon 12/149:05 pm -
1 stop11h 00m
Deal found 11/9![Southwest logo]()
$424
This Delta deal was found by Cheapflights users on 11/11. 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 12/99:37 am -
2 stops14h 41m
Wed 12/169:44 pm -
2 stops16h 17m
Deal found 11/11![Delta logo]()
$435
This Delta deal was found by Cheapflights users on 11/10. 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.
Sun 11/229:30 am -
2 stops14h 37m
Thu 11/269:45 pm -
2 stops14h 54m
Deal found 11/10![Delta logo]()
$465
This Delta deal was found by Cheapflights users on 11/10. 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.
Sat 11/149:30 am -
2 stops14h 37m
Sat 11/2110:59 pm -
2 stops13h 40m
Deal found 11/10![Delta logo]()
$495
This Southwest deal was found by Cheapflights users on 11/11. 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 12/95:50 am -
1 stop11h 25m
Wed 12/169:05 pm -
1 stop12h 25m
Deal found 11/11![Southwest logo]()
$504
This Delta deal was found by Cheapflights users on 11/13. 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.
Sat 11/149:30 am -
2 stops14h 37m
Sun 11/159:45 pm -
2 stops16h 19m
Deal found 11/13![Delta logo]()
$505
This Southwest deal was found by Cheapflights users on 11/11. 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.
Thu 11/125:45 am -
1 stop11h 30m
Mon 11/169:05 pm -
1 stop11h 00m
Deal found 11/11![Southwest logo]()
$534
This Southwest deal was found by Cheapflights users on 11/11. 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 12/610:00 am -
2 stops15h 30m
Sun 12/1311:50 am -
2 stops14h 05m
Deal found 11/11![Southwest logo]()
$545
This Southwest deal was found by Cheapflights users on 11/9. 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 12/910:05 am -
1 stop13h 25m
Wed 12/163:15 pm -
1 stop10h 40m
Deal found 11/9![Southwest logo]()
$578
This Southwest deal was found by Cheapflights users on 11/9. 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 12/75:50 am -
1 stop13h 35m
Mon 12/143:15 pm -
1 stop17h 15m
Deal found 11/9![Southwest logo]()
$582
This Southwest deal was found by Cheapflights users on 11/9. 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 12/710:10 am -
1 stop15h 10m
Fri 12/1111:15 pm -
2 stops14h 40m
Deal found 11/9![Southwest logo]()
$584
This Delta deal was found by Cheapflights users on 11/10. 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 12/156:00 am -
1 stop12h 55m
Mon 12/214:40 pm -
1 stop12h 09m
Deal found 11/10![Delta logo]()
$586
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 November 14, 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 November 14, 2026.
This Southwest deal was found by Cheapflights users on 11/9. 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 12/75:50 am -
1 stop11h 25m
Mon 12/149:05 pm -
1 stop11h 00m
Deal found 11/9![Southwest logo]()
$424
This Delta deal was found by Cheapflights users on 11/13. 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.
Thu 1/79:38 am -
2 stops14h 43m
Thu 1/149:46 pm -
2 stops15h 07m
Deal found 11/13![Delta logo]()
$445
This Delta deal was found by Cheapflights users on 11/9. 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 12/79:37 am -
2 stops14h 41m
Mon 12/149:44 pm -
2 stops15h 06m
Deal found 11/9![Delta logo]()
$465
This Southwest deal was found by Cheapflights users on 11/12. 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 2/210:00 am -
2 stops14h 50m
Thu 2/1110:45 am -
2 stops13h 45m
Deal found 11/12![Southwest logo]()
$589
This Delta deal was found by Cheapflights users on 11/11. 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 1/279:38 am -
2 stops14h 22m
Wed 2/39:40 pm -
2 stops15h 13m
Deal found 11/11![Delta logo]()
$589
This Southwest deal was found by Cheapflights users on 11/12. 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 1/2810:00 am -
1 stop12h 05m
Mon 2/111:20 pm -
2 stops13h 15m
Deal found 11/12![Southwest logo]()
$592
This Delta deal was found by Cheapflights users on 11/13. 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 3/169:30 am -
2 stops14h 54m
Tue 3/238:52 pm -
1 stop9h 59m
Deal found 11/13![Delta logo]()
$592
This Southwest deal was found by Cheapflights users on 11/9. 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 11/3010:55 pm -
1 stop18h 00m
Thu 12/38:15 pm -
2 stops12h 00m
Deal found 11/9![Southwest logo]()
$615
This Delta deal was found by Cheapflights users on 11/13. 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.
Wed 2/246:00 am -
1 stop12h 59m
Mon 3/14:49 pm -
1 stop12h 11m
Deal found 11/13![Delta logo]()
$596
This Southwest deal was found by Cheapflights users on 11/12. 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 11/255:50 am -
1 stop11h 25m
Fri 12/411:50 am -
2 stops14h 05m
Deal found 11/12![Southwest logo]()
$618
This Delta deal was found by Cheapflights users on 11/9. 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 3/169:30 am -
2 stops14h 54m
Tue 3/304:05 pm -
2 stops14h 51m
Deal found 11/9![Delta logo]()
$597
This Southwest deal was found by Cheapflights users on 11/9. 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.
Fri 2/197:00 am -
1 stop15h 30m
Fri 2/264:05 pm -
1 stop15h 55m
Deal found 11/9![Southwest logo]()
$624
This Delta deal was found by Cheapflights users on 11/14. 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.
Tue 1/269:38 am -
2 stops14h 22m
Tue 2/29:40 pm -
2 stops16h 20m
Deal found 11/14![Delta logo]()
$597
This Southwest deal was found by Cheapflights users on 11/9. 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.
Fri 12/1110:15 am -
1 stop14h 50m
Mon 12/218:15 am -
1 stop16h 45m
Deal found 11/9![Southwest logo]()
$628
This Delta deal was found by Cheapflights users on 11/12. 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.
Wed 1/279:38 am -
2 stops14h 22m
Tue 2/29:40 pm -
2 stops15h 13m
Deal found 11/12![Delta logo]()
$599
This Southwest deal was found by Cheapflights users on 11/11. 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 2/267:00 am -
1 stop15h 30m
Wed 3/1011:20 pm -
1 stop14h 35m
Deal found 11/11![Southwest logo]()
$628
This Delta deal was found by Cheapflights users on 11/12. 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.
Sun 1/179:38 am -
2 stops14h 22m
Fri 1/228:40 pm -
2 stops15h 42m
Deal found 11/12![Delta logo]()
$599
This Southwest deal was found by Cheapflights users on 11/9. 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 12/145:50 am -
1 stop11h 25m
Mon 12/219:05 pm -
2 stops13h 25m
Deal found 11/9![Southwest logo]()
$635
This Delta deal was found by Cheapflights users on 11/11. 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 1/269:38 am -
2 stops14h 41m
Wed 2/39:15 pm -
2 stops16h 45m
Deal found 11/11![Delta logo]()
$607
This Southwest deal was found by Cheapflights users on 11/13. 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.
Thu 1/710:00 am -
2 stops14h 35m
Thu 1/149:30 pm -
1 stop11h 05m
Deal found 11/13![Southwest logo]()
$642
This Delta deal was found by Cheapflights users on 11/11. 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 11/266:00 am -
1 stop12h 40m
Mon 12/144:25 pm -
1 stop13h 12m
Deal found 11/11![Delta logo]()
$628
This Southwest deal was found by Cheapflights users on 11/13. 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 12/25:50 am -
1 stop12h 10m
Wed 12/99:30 pm -
1 stop12h 45m
Deal found 11/13![Southwest logo]()
$670
This Delta deal was found by Cheapflights users on 11/10. 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 12/89:37 am -
2 stops15h 20m
Tue 12/159:35 pm -
1 stop10h 24m
Deal found 11/10![Delta logo]()
$634
This Southwest deal was found by Cheapflights users on 11/9. 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 11/295:45 am -
2 stops14h 25m
Thu 12/310:30 pm -
1 stop10h 00m
Deal found 11/9![Southwest logo]()
$677
This Delta deal was found by Cheapflights users on 11/13. 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 1/199:38 am -
2 stops14h 41m
Tue 1/269:15 pm -
2 stops15h 38m
Deal found 11/13![Delta logo]()
$642
This Southwest deal was found by Cheapflights users on 11/9. 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.
Fri 1/2210:15 am -
2 stops14h 25m
Fri 1/299:25 pm -
2 stops13h 55m
Deal found 11/9![Southwest logo]()
$677
This Delta deal was found by Cheapflights users on 11/10. 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.
Wed 1/69:38 am -
2 stops14h 51m
Wed 1/138:25 pm -
2 stops16h 30m
Deal found 11/10![Delta logo]()
$676
This Southwest deal was found by Cheapflights users on 11/9. 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 11/185:20 am -
1 stop11h 35m
Tue 11/249:25 pm -
1 stop11h 45m
Deal found 11/9![Southwest logo]()
$680
This Delta deal was found by Cheapflights users on 11/9. 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.
Fri 1/86:00 am -
1 stop12h 59m
Thu 1/145:57 pm -
1 stop11h 01m
Deal found 11/9![Delta logo]()
$680
This Southwest deal was found by Cheapflights users on 11/12. 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 12/310:00 am -
2 stops13h 45m
Mon 12/711:15 pm -
2 stops14h 15m
Deal found 11/12![Southwest logo]()
$681
Last-minute flights from Midway to HawaiiDiscover last-minute flight deals from Midway to Hawaii. Data last updated November 14, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Hawaii. Data last updated November 14, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 11/11. 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.
Thu 11/125:45 am -
1 stop11h 30m
Mon 11/169:05 pm -
1 stop11h 00m
Deal found 11/11![Southwest logo]()
$534
This Delta deal was found by Cheapflights users on 11/10. 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.
Sat 11/149:30 am -
2 stops14h 37m
Sat 11/2110:59 pm -
2 stops13h 40m
Deal found 11/10![Delta logo]()
$495
This Delta deal was found by Cheapflights users on 11/13. 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.
Sat 11/149:30 am -
2 stops14h 37m
Sun 11/159:45 pm -
2 stops16h 19m
Deal found 11/13![Delta logo]()
$505
This Delta deal was found by Cheapflights users on 11/10. 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.
Sun 11/229:30 am -
2 stops14h 37m
Thu 11/269:45 pm -
2 stops14h 54m
Deal found 11/10![Delta logo]()
$465
This Southwest deal was found by Cheapflights users on 11/11. 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 12/610:00 am -
2 stops15h 30m
Sun 12/1311:50 am -
2 stops14h 05m
Deal found 11/11![Southwest logo]()
$545
This Southwest deal was found by Cheapflights users on 11/9. 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 12/75:50 am -
1 stop11h 25m
Mon 12/149:05 pm -
1 stop11h 00m
Deal found 11/9![Southwest logo]()
$424
This Southwest deal was found by Cheapflights users on 11/9. 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 12/75:50 am -
1 stop13h 35m
Mon 12/143:15 pm -
1 stop17h 15m
Deal found 11/9![Southwest logo]()
$582
This Southwest deal was found by Cheapflights users on 11/9. 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 12/710:10 am -
1 stop15h 10m
Fri 12/1111:15 pm -
2 stops14h 40m
Deal found 11/9![Southwest logo]()
$584
This Delta deal was found by Cheapflights users on 11/11. 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 12/99:37 am -
2 stops14h 41m
Wed 12/169:44 pm -
2 stops16h 17m
Deal found 11/11![Delta logo]()
$435
This Southwest deal was found by Cheapflights users on 11/11. 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 12/95:50 am -
1 stop11h 25m
Wed 12/169:05 pm -
1 stop12h 25m
Deal found 11/11![Southwest logo]()
$504
This Southwest deal was found by Cheapflights users on 11/9. 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 12/910:05 am -
1 stop13h 25m
Wed 12/163:15 pm -
1 stop10h 40m
Deal found 11/9![Southwest logo]()
$578
This Delta deal was found by Cheapflights users on 11/10. 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 12/156:00 am -
1 stop12h 55m
Mon 12/214:40 pm -
1 stop12h 09m
Deal found 11/10![Delta logo]()
$586
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 November 14, 2026.
Search for one-way flight options from Midway to Hawaii. Find affordable one-way fares based on user searches. Data last updated November 14, 2026.
This Delta deal was found by Cheapflights users on 11/9. 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 1/179:38 am -
2 stops14h 43m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/9![Delta logo]()
$218
This Southwest deal was found by Cheapflights users on 11/10. 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.
Wed 1/1310:15 am -
1 stop12h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/10![Southwest logo]()
$289
This Southwest deal was found by Cheapflights users on 11/11. 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 1/185:20 am -
1 stop11h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/11![Southwest logo]()
$289
This Delta deal was found by Cheapflights users on 11/10. 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.
Wed 3/36:00 am -
1 stop12h 59m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/10![Delta logo]()
$293
This Southwest deal was found by Cheapflights users on 11/10. 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 1/1710:00 am -
2 stops14h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/10![Southwest logo]()
$295
This Southwest deal was found by Cheapflights users on 11/12. 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.
Sun 1/3110:10 am -
2 stops14h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/12![Southwest logo]()
$295
This Southwest deal was found by Cheapflights users on 11/12. 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.
Mon 12/75:20 am -
2 stops12h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/12![Southwest logo]()
$296
This Delta deal was found by Cheapflights users on 11/10. 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 1/196:00 am -
1 stop12h 59m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/10![Delta logo]()
$298
This Delta deal was found by Cheapflights users on 11/11. 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 3/309:30 am -
2 stops14h 52m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/11![Delta logo]()
$298
This Delta deal was found by Cheapflights users on 11/13. 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.
Wed 2/179:46 am -
2 stops16h 07m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/13![Delta logo]()
$299
This Southwest deal was found by Cheapflights users on 11/13. 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 12/910:05 am -
2 stops15h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/13![Southwest logo]()
$299
This Southwest deal was found by Cheapflights users on 11/12. 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 2/2010:10 am -
2 stops14h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/12![Southwest logo]()
$303
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 November 14, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $424 (Southwest) |
One-way from | $218 (Delta) |
Popular in | June |
Cheapest in | February |
Average price | $731 |
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 7,457,451 searches. Data last updated November 14, 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 Chicago Midway - LIH Lihue
MDWLIH
Chicago Midway
Sun 1/17
9:38 am-8:21 pm
2 stops14h 43m
Lihue
Wed 12/31
12:00 am-4:00 am
Nonstop0h 00m
$218
ChicagoHonolulu
MDW Chicago Midway - HNL Honolulu
MDWHNL
Chicago Midway
Wed 3/3
6:00 am-2:59 pm
1 stop12h 59m
Honolulu
Wed 12/31
12:00 am-4:00 am
Nonstop0h 00m
$293
ChicagoHonolulu
MDW Chicago Midway - HNL Honolulu
MDWHNL
Chicago Midway
Tue 12/15
6:00 am-2:55 pm
1 stop12h 55m
Honolulu
Wed 12/31
12:00 am-4:00 am
Nonstop0h 00m
$293
ChicagoHonolulu
MDW Chicago Midway - HNL Honolulu
MDWHNL
Chicago Midway
Thu 4/8
6:00 am-4:33 pm
1 stop15h 33m
Honolulu
Wed 12/31
12:00 am-4:00 am
Nonstop0h 00m
$293
ChicagoHonolulu
MDW Chicago Midway - HNL Honolulu
MDWHNL
Chicago Midway
Wed 2/17
6:00 am-2:59 pm
1 stop12h 59m
Honolulu
Wed 12/31
12:00 am-4:00 am
Nonstop0h 00m
$293
ChicagoHonolulu
MDW Chicago Midway - HNL Honolulu
MDWHNL
Chicago Midway
Thu 3/4
6:00 am-2:59 pm
1 stop12h 59m
Honolulu
Wed 12/31
12:00 am-4:00 am
Nonstop0h 00m
$298
ChicagoKahului
MDW Chicago Midway - OGG Kahului
MDWOGG
Chicago Midway
Wed 1/20
6:00 am-2:59 pm
1 stop12h 59m
Kahului
Wed 12/31
12:00 am-4:00 am
Nonstop0h 00m
$298
ChicagoHonolulu
MDW Chicago Midway - HNL Honolulu
MDWHNL
Chicago Midway
Wed 1/13
9:38 am-8:29 pm
2 stops14h 51m
Honolulu
Wed 12/31
12:00 am-4:00 am
Nonstop0h 00m
$299
ChicagoLihue
MDW Chicago Midway - LIH Lihue
MDWLIH
Chicago Midway
Sat 2/20
10:10 am-8:35 pm
2 stops14h 25m
Lihue
Wed 12/31
12:00 am-4:00 am
Nonstop0h 00m
$303
ChicagoKahului
MDW Chicago Midway - OGG Kahului
MDWOGG
Chicago Midway
Tue 1/19
6:00 am-2:59 pm
1 stop12h 59m
Kahului
Wed 12/31
12:00 am-4:00 am
Nonstop0h 00m
$303
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-OGG
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-LIH
MDW-HNL
MDW-KOA
MDW-OGG
How much does it cost to fly round-trip from Chicago Midway Airport to Hawaii?
Airfare is below average for this route at the moment.
Chicago Midway Airport to Hawaii flights typically cost between $590 and $680 in December.The cheapest round-trip price found within the last 5 days was $578 on Southwest (Dec 9-Dec 16).
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 November 14, 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
Overall
8.0
Food
7.0
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Comfort
8.0
Crew
8.6
Overall
8.0
Food
7.0
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - 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.
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 November 14, 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 7,457,451 searches. Data last updated November 14, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$536 | Average$809 | FlexibilityNo cancel fee | On-time63% |