$217+ 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 11/16. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — HNL
Sep 14 — Sep 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 August 15, 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 August 15, 2026.
This Southwest deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/95:45 am -
1 stop11h 35m
Thu 11/129:25 pm -
1 stop10h 25m
Deal found 8/10![Southwest logo]()
$434
This Southwest deal was found by Cheapflights users on 8/13. 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 10/276:05 am -
1 stop11h 30m
Tue 11/311:50 am -
2 stops14h 05m
Deal found 8/13![Southwest logo]()
$435
This Southwest deal was found by Cheapflights users on 8/13. 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 11/125:45 am -
1 stop11h 30m
Mon 11/169:05 pm -
1 stop13h 05m
Deal found 8/13![Southwest logo]()
$444
This Delta deal was found by Cheapflights users on 8/10. 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 12/69:30 am -
2 stops14h 43m
Sat 12/129:40 pm -
2 stops16h 24m
Deal found 8/10![Delta logo]()
$445
This Southwest deal was found by Cheapflights users on 8/13. 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 11/95:45 am -
1 stop11h 30m
Wed 11/1811:50 am -
2 stops14h 05m
Deal found 8/13![Southwest logo]()
$475
This Southwest deal was found by Cheapflights users on 8/10. 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 11/110:15 am -
2 stops15h 15m
Sat 11/74:05 pm -
1 stop15h 30m
Deal found 8/10![Southwest logo]()
$480
This Delta deal was found by Cheapflights users on 8/11. 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 9/239:29 am -
2 stops14h 41m
Wed 9/309:54 pm -
2 stops15h 39m
Deal found 8/11![Delta logo]()
$485
This Southwest deal was found by Cheapflights users on 8/13. 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 10/299:50 am -
2 stops13h 20m
Sun 11/14:05 pm -
1 stop15h 30m
Deal found 8/13![Southwest logo]()
$510
This Southwest deal was found by Cheapflights users on 8/13. 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 11/95:45 am -
1 stop11h 55m
Wed 11/1811:40 am -
2 stops14h 15m
Deal found 8/13![Southwest logo]()
$510
This Southwest deal was found by Cheapflights users on 8/11. 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 11/610:05 am -
2 stops15h 20m
Thu 11/129:30 pm -
1 stop10h 20m
Deal found 8/11![Southwest logo]()
$524
This Southwest deal was found by Cheapflights users on 8/13. 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 stop11h 20m
Fri 12/117:00 pm -
2 stops13h 25m
Deal found 8/13![Southwest logo]()
$533
This Southwest deal was found by Cheapflights users on 8/12. 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.
Fri 11/275:10 am -
1 stop11h 45m
Fri 12/48:15 pm -
1 stop10h 20m
Deal found 8/12![Southwest logo]()
$536
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 August 15, 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 August 15, 2026.
This Southwest deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/95:45 am -
1 stop11h 35m
Thu 11/1211:35 am -
2 stops14h 20m
Deal found 8/10![Southwest logo]()
$440
This Delta deal was found by Cheapflights users on 8/10. 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 9/221:19 pm -
2 stops26h 47m
Mon 9/289:10 pm -
2 stops16h 23m
Deal found 8/10![Delta logo]()
$652
This Southwest deal was found by Cheapflights users on 8/14. 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 11/185:50 am -
1 stop12h 10m
Sun 11/2211:40 am -
2 stops14h 15m
Deal found 8/14![Southwest logo]()
$561
This Southwest deal was found by Cheapflights users on 8/11. 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 11/65:45 am -
1 stop11h 55m
Thu 11/129:00 am -
1 stop16h 45m
Deal found 8/11![Southwest logo]()
$584
This Delta deal was found by Cheapflights users on 8/13. 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 12/56:00 am -
1 stop12h 59m
Fri 12/115:20 pm -
1 stop11h 30m
Deal found 8/13![Delta logo]()
$674
This Southwest deal was found by Cheapflights users on 8/14. 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.
Tue 2/910:15 am -
2 stops15h 10m
Tue 2/167:05 pm -
2 stops13h 30m
Deal found 8/14![Southwest logo]()
$595
This Delta deal was found by Cheapflights users on 8/10. 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 8/189:24 am -
2 stops14h 52m
Thu 8/279:55 pm -
2 stops15h 38m
Deal found 8/10![Delta logo]()
$675
This Southwest deal was found by Cheapflights users on 8/13. 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 1/2610:00 am -
2 stops15h 25m
Tue 2/27:05 pm -
2 stops12h 15m
Deal found 8/13![Southwest logo]()
$595
This Delta deal was found by Cheapflights users on 8/13. 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.
Fri 2/56:00 am -
1 stop12h 52m
Fri 2/1212:45 pm -
2 stops16h 00m
Deal found 8/13![Delta logo]()
$680
This Delta deal was found by Cheapflights users on 8/14. 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.
Mon 9/289:59 am -
2 stops14h 16m
Mon 10/510:10 pm -
2 stops13h 37m
Deal found 8/14![Delta logo]()
$680
This Southwest deal was found by Cheapflights users on 8/14. 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 9/146:40 am -
1 stop10h 55m
Mon 9/218:25 pm -
1 stop10h 30m
Deal found 8/14![Southwest logo]()
$623
This Delta deal was found by Cheapflights users on 8/12. 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 1/276:00 am -
1 stop12h 52m
Sat 1/3012:45 pm -
2 stops16h 04m
Deal found 8/12![Delta logo]()
$690
This Southwest deal was found by Cheapflights users on 8/11. 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 10/2010:15 am -
2 stops13h 00m
Mon 10/268:45 pm -
1 stop11h 40m
Deal found 8/11![Southwest logo]()
$630
This Southwest deal was found by Cheapflights users on 8/11. 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 10/2110:15 am -
2 stops13h 00m
Mon 10/268:45 pm -
1 stop11h 40m
Deal found 8/11![Southwest logo]()
$630
This Delta deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/112:30 pm -
2 stops13h 23m
Tue 2/94:30 pm -
1 stop13h 22m
Deal found 8/11![Delta logo]()
$716
This Southwest deal was found by Cheapflights users on 8/13. 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 8/2510:15 am -
1 stop10h 55m
Sun 8/309:25 pm -
2 stops13h 45m
Deal found 8/13![Southwest logo]()
$640
This Delta deal was found by Cheapflights users on 8/12. 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 8/269:59 am -
2 stops14h 18m
Sat 8/2910:05 pm -
2 stops14h 56m
Deal found 8/12![Delta logo]()
$725
This Southwest deal was found by Cheapflights users on 8/11. 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 11/67:25 am -
2 stops17h 40m
Mon 11/98:00 am -
2 stops13h 05m
Deal found 8/11![Southwest logo]()
$649
This Delta deal was found by Cheapflights users on 8/11. 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.
Sat 12/59:30 am -
2 stops14h 34m
Sat 12/125:20 pm -
2 stops15h 15m
Deal found 8/11![Delta logo]()
$745
This Southwest deal was found by Cheapflights users on 8/14. 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 9/2811:10 am -
2 stops15h 10m
Tue 10/610:25 pm -
2 stops12h 20m
Deal found 8/14![Southwest logo]()
$650
This Delta deal was found by Cheapflights users on 8/11. 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 10/286:04 am -
2 stops16h 55m
Wed 11/48:59 pm -
2 stops17h 01m
Deal found 8/11![Delta logo]()
$759
This Southwest deal was found by Cheapflights users on 8/11. 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 9/106:40 am -
2 stops12h 30m
Thu 9/178:25 pm -
1 stop10h 40m
Deal found 8/11![Southwest logo]()
$651
This Delta deal was found by Cheapflights users on 8/14. 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.
Sat 1/235:35 pm -
2 stops29h 11m
Sat 1/3012:45 pm -
2 stops16h 04m
Deal found 8/14![Delta logo]()
$787
This Southwest deal was found by Cheapflights users on 8/14. 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 9/286:40 am -
2 stops12h 30m
Mon 10/511:50 am -
2 stops13h 05m
Deal found 8/14![Southwest logo]()
$652
This Southwest deal was found by Cheapflights users on 8/10. 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.
Fri 1/225:20 am -
2 stops15h 20m
Fri 1/2911:20 pm -
1 stop10h 10m
Deal found 8/10![Southwest logo]()
$654
This Southwest deal was found by Cheapflights users on 8/13. 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.
Sun 9/275:25 am -
1 stop12h 10m
Sun 10/412:15 pm -
2 stops12h 30m
Deal found 8/13![Southwest logo]()
$664
This Southwest deal was found by Cheapflights users on 8/14. 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 10/2311:50 am -
2 stops14h 35m
Wed 11/43:15 pm -
1 stop16h 20m
Deal found 8/14![Southwest logo]()
$665
This Southwest deal was found by Cheapflights users on 8/13. 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.
Sun 10/1810:00 am -
2 stops16h 30m
Wed 10/2812:15 pm -
1 stop12h 40m
Deal found 8/13![Southwest logo]()
$671
This Southwest deal was found by Cheapflights users on 8/13. 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.
Sun 11/295:30 am -
2 stops16h 40m
Sat 12/126:00 am -
2 stops12h 50m
Deal found 8/13![Southwest logo]()
$679
This Southwest deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/246:40 am -
1 stop10h 55m
Thu 10/111:40 am -
2 stops13h 15m
Deal found 8/10![Southwest logo]()
$680
Last-minute flights from Midway to HawaiiDiscover last-minute flight deals from Midway to Hawaii. Data last updated August 15, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Hawaii. Data last updated August 15, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 8/12. 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 8/186:40 am -
2 stops14h 30m
Mon 8/248:25 pm -
1 stop10h 30m
Deal found 8/12![Southwest logo]()
$590
This Southwest deal was found by Cheapflights users on 8/11. 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 8/216:15 am -
2 stops16h 50m
Tue 9/18:25 pm -
1 stop12h 05m
Deal found 8/11![Southwest logo]()
$613
This Southwest deal was found by Cheapflights users on 8/11. 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 8/276:40 am -
1 stop10h 55m
Tue 9/18:25 pm -
1 stop12h 05m
Deal found 8/11![Southwest logo]()
$574
This Southwest deal was found by Cheapflights users on 8/10. 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 9/26:50 am -
2 stops12h 20m
Fri 9/118:25 pm -
1 stop10h 40m
Deal found 8/10![Southwest logo]()
$624
This Southwest deal was found by Cheapflights users on 8/13. 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 9/102:50 pm -
1 stop11h 35m
Mon 9/1411:55 am -
1 stop12h 50m
Deal found 8/13![Southwest logo]()
$624
This Southwest deal was found by Cheapflights users on 8/14. 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 9/146:40 am -
1 stop10h 55m
Mon 9/218:25 pm -
1 stop10h 30m
Deal found 8/14![Southwest logo]()
$623
This Southwest deal was found by Cheapflights users on 8/14. 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.
Tue 9/156:40 am -
2 stops14h 30m
Tue 9/228:55 pm -
1 stop11h 00m
Deal found 8/14![Southwest logo]()
$590
This Southwest deal was found by Cheapflights users on 8/14. 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 9/166:50 am -
2 stops14h 20m
Tue 9/228:55 pm -
1 stop11h 00m
Deal found 8/14![Southwest logo]()
$620
This Southwest deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/226:50 am -
1 stop10h 45m
Mon 9/288:55 pm -
1 stop11h 00m
Deal found 8/10![Southwest logo]()
$624
This Delta deal was found by Cheapflights users on 8/11. 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 9/239:29 am -
2 stops14h 41m
Wed 9/309:54 pm -
2 stops15h 39m
Deal found 8/11![Delta logo]()
$485
This Delta deal was found by Cheapflights users on 8/10. 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 9/231:19 pm -
2 stops26h 47m
Mon 9/289:10 pm -
2 stops16h 23m
Deal found 8/10![Delta logo]()
$619
This Southwest deal was found by Cheapflights users on 8/14. 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 9/286:40 am -
1 stop10h 55m
Mon 10/512:15 pm -
1 stop12h 40m
Deal found 8/14![Southwest logo]()
$619
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 August 15, 2026.
Search for one-way flight options from Midway to Hawaii. Find affordable one-way fares based on user searches. Data last updated August 15, 2026.
This Southwest deal was found by Cheapflights users on 8/12. 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 11/165:50 am -
1 stop12h 10m
Deal found 8/12![Southwest logo]()
$217
This Delta deal was found by Cheapflights users on 8/11. 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 10/289:29 am -
2 stops14h 45m
Deal found 8/11![Delta logo]()
$218
This Southwest deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/316:40 am -
1 stop10h 55m
Deal found 8/10![Southwest logo]()
$223
This Delta deal was found by Cheapflights users on 8/13. 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.
Fri 11/139:30 am -
2 stops14h 43m
Deal found 8/13![Delta logo]()
$228
This Delta deal was found by Cheapflights users on 8/11. 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 9/19:24 am -
2 stops16h 56m
Deal found 8/11![Delta logo]()
$250
This Delta deal was found by Cheapflights users on 8/14. 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.
Sun 11/156:00 am -
2 stops18h 57m
Deal found 8/14![Delta logo]()
$251
This Southwest deal was found by Cheapflights users on 8/11. 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 10/286:05 am -
1 stop11h 30m
Deal found 8/11![Southwest logo]()
$252
This Southwest deal was found by Cheapflights users on 8/12. 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 2/810:20 am -
2 stops15h 10m
Deal found 8/12![Southwest logo]()
$258
This Delta deal was found by Cheapflights users on 8/14. 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.
Sat 9/129:29 am -
2 stops16h 43m
Deal found 8/14![Delta logo]()
$270
This Delta deal was found by Cheapflights users on 8/13. 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 11/125:09 pm -
2 stops23h 06m
Deal found 8/13![Delta logo]()
$272
This Southwest deal was found by Cheapflights users on 8/12. 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 12/145:50 am -
1 stop11h 25m
Deal found 8/12![Southwest logo]()
$272
This Delta deal was found by Cheapflights users on 8/13. 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 9/249:29 am -
2 stops14h 41m
Deal found 8/13![Delta logo]()
$278
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 August 15, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $434 (Southwest) |
One-way from | $217 (Southwest) |
Popular in | June |
Cheapest in | February |
Average price | $908 |
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 August 15, 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
ChicagoHilo
MDW Chicago Midway - ITO Hilo Intl
MDWITO
Chicago Midway
Mon 11/9
5:45 am-1:20 pm
1 stop11h 35m
Hilo Intl
Thu 11/12
11:35 am-5:55 am
2 stops14h 20m
$440
ChicagoKailua-Kona
MDW Chicago Midway - KOA Kona Intl
MDWKOA
Chicago Midway
Wed 11/18
5:50 am-2:00 pm
1 stop12h 10m
Kona Intl
Sun 11/22
11:40 am-5:55 am
2 stops14h 15m
$561
ChicagoKailua-Kona
MDW Chicago Midway - KOA Kona Intl
MDWKOA
Chicago Midway
Fri 11/6
5:45 am-1:40 pm
1 stop11h 55m
Kona Intl
Thu 11/12
9:00 am-5:45 am
1 stop16h 45m
$584
ChicagoKailua-Kona
MDW Chicago Midway - KOA Kona Intl
MDWKOA
Chicago Midway
Tue 2/9
10:15 am-9:25 pm
2 stops15h 10m
Kona Intl
Tue 2/16
7:05 pm-12:35 pm
2 stops13h 30m
$595
ChicagoKailua-Kona
MDW Chicago Midway - KOA Kona Intl
MDWKOA
Chicago Midway
Tue 1/26
10:00 am-9:25 pm
2 stops15h 25m
Kona Intl
Tue 2/2
7:05 pm-11:20 am
2 stops12h 15m
$595
Quickest round-trip
ChicagoLihue
MDW Chicago Midway - LIH Lihue
MDWLIH
Chicago Midway
Mon 9/14
6:40 am-12:35 pm
1 stop10h 55m
Lihue
Mon 9/21
8:25 pm-11:55 am
1 stop10h 30m
$623
ChicagoHilo
MDW Chicago Midway - ITO Hilo Intl
MDWITO
Chicago Midway
Tue 10/20
10:15 am-6:15 pm
2 stops13h 00m
Hilo Intl
Mon 10/26
8:45 pm-1:25 pm
1 stop11h 40m
$630
ChicagoHilo
MDW Chicago Midway - ITO Hilo Intl
MDWITO
Chicago Midway
Wed 10/21
10:15 am-6:15 pm
2 stops13h 00m
Hilo Intl
Mon 10/26
8:45 pm-1:25 pm
1 stop11h 40m
$630
ChicagoLihue
MDW Chicago Midway - LIH Lihue
MDWLIH
Chicago Midway
Tue 8/25
10:15 am-4:10 pm
1 stop10h 55m
Lihue
Sun 8/30
9:25 pm-4:10 pm
2 stops13h 45m
$640
ChicagoHonolulu
MDW Chicago Midway - HNL Honolulu
MDWHNL
Chicago Midway
Fri 11/6
7:25 am-9:05 pm
2 stops17h 40m
Honolulu
Mon 11/9
8:00 am-1:05 am
2 stops13h 05m
$649
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-ITO
MDW-OGG
MDW-KOA
MDW-LIH
MDW-HNL
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-ITO
MDW-OGG
MDW-KOA
MDW-LIH
What is the cheapest month to book a flight from Chicago Midway Airport to Hawaii?
Currently, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Hawaii (average of $465). Flying from Chicago Midway Airport to Hawaii in June is currently the most expensive (average of $1,011). 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?
Airfare is typical for this route at the moment.
Chicago Midway Airport to Hawaii flights typically cost between $621 and $723 in September.The cheapest round-trip price found within the last 5 days was $624 on Southwest (Sep 10-Sep 14).
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 August 15, 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
Food
7.0
Overall
8.0
Crew
8.6
Entertainment
7.5
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Comfort
8.0
Food
7.0
Overall
8.0
Crew
8.6
Entertainment
7.5
Boarding
8.1
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.
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 August 15, 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 August 15, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$553 | Average$808 | FlexibilityNo cancel fee | On-time63% |