$212+ 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 12/9. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — HNL
Oct 29 — Nov 51
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 September 29, 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 September 29, 2026.
This Delta deal was found by Cheapflights users on 9/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/319:29 am -
2 stops14h 45m
Sun 11/810:51 pm -
2 stops15h 13m
Deal found 9/27![Delta logo]()
$435
This Southwest deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/66:05 am -
1 stop11h 30m
Tue 10/1312:15 pm -
1 stop12h 40m
Deal found 9/28![Southwest logo]()
$474
This Southwest deal was found by Cheapflights users on 9/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/265:10 am -
1 stop12h 25m
Mon 11/24:05 pm -
1 stop16h 25m
Deal found 9/26![Southwest logo]()
$489
This Southwest deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/195:10 am -
1 stop12h 25m
Mon 10/2612:15 pm -
1 stop12h 40m
Deal found 9/28![Southwest logo]()
$494
This Southwest deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/295:10 am -
1 stop12h 25m
Thu 11/59:30 pm -
1 stop10h 20m
Deal found 9/29![Southwest logo]()
$527
This Southwest deal was found by Cheapflights users on 9/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/316:35 am -
1 stop11h 00m
Sun 11/811:50 am -
2 stops14h 05m
Deal found 9/27![Southwest logo]()
$530
This Southwest deal was found by Cheapflights users on 9/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/255:20 am -
1 stop12h 15m
Sun 11/14:05 pm -
1 stop15h 30m
Deal found 9/25![Southwest logo]()
$544
This Delta deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/119:30 am -
2 stops14h 37m
Sun 11/159:45 pm -
2 stops16h 19m
Deal found 9/28![Delta logo]()
$545
This Delta deal was found by Cheapflights users on 9/24. Clicking the “Pick Dates” 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 10/249:29 am -
2 stops14h 45m
Sat 10/319:45 pm -
2 stops16h 15m
Deal found 9/24![Delta logo]()
$551
This Delta deal was found by Cheapflights users on 9/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/74:19 pm -
2 stops23h 45m
Wed 11/111:35 pm -
2 stops16h 11m
Deal found 9/27![Delta logo]()
$560
This Southwest deal was found by Cheapflights users on 9/24. Clicking the “Pick Dates” 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 10/265:40 am -
1 stop12h 35m
Mon 11/98:15 am -
1 stop16h 45m
Deal found 9/24![Southwest logo]()
$562
This Southwest deal was found by Cheapflights users on 9/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/265:40 am -
1 stop12h 35m
Tue 11/103:15 pm -
1 stop10h 40m
Deal found 9/25![Southwest logo]()
$570
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 September 29, 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 September 29, 2026.
This Southwest deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/66:05 am -
1 stop11h 30m
Tue 10/1312:15 pm -
1 stop12h 40m
Deal found 9/28![Southwest logo]()
$474
This Delta deal was found by Cheapflights users on 9/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/56:04 am -
2 stops18h 55m
Thu 11/121:59 pm -
2 stops14h 51m
Deal found 9/27![Delta logo]()
$579
This Southwest deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/216:05 am -
1 stop11h 30m
Mon 10/2611:50 am -
2 stops13h 05m
Deal found 9/29![Southwest logo]()
$500
This Southwest deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/295:10 am -
1 stop12h 25m
Thu 11/59:30 pm -
1 stop10h 20m
Deal found 9/29![Southwest logo]()
$527
This Delta deal was found by Cheapflights users on 9/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/19:29 am -
2 stops15h 19m
Thu 11/54:15 pm -
1 stop13h 17m
Deal found 9/25![Delta logo]()
$634
This Southwest deal was found by Cheapflights users on 9/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/316:35 am -
1 stop11h 00m
Sun 11/811:50 am -
2 stops14h 05m
Deal found 9/27![Southwest logo]()
$530
This Delta deal was found by Cheapflights users on 9/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/69:29 am -
2 stops14h 45m
Tue 11/109:45 pm -
2 stops16h 19m
Deal found 9/27![Delta logo]()
$645
This Southwest deal was found by Cheapflights users on 9/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/255:20 am -
1 stop12h 15m
Sun 11/14:05 pm -
1 stop15h 30m
Deal found 9/25![Southwest logo]()
$544
This Delta deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/46:05 am -
1 stop12h 23m
Tue 10/61:05 pm -
2 stops15h 27m
Deal found 9/28![Delta logo]()
$676
This Southwest deal was found by Cheapflights users on 9/24. Clicking the “Pick Dates” 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 10/246:15 am -
1 stop11h 20m
Sat 10/3112:15 pm -
1 stop11h 50m
Deal found 9/24![Southwest logo]()
$584
This Delta deal was found by Cheapflights users on 9/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/189:30 am -
2 stops15h 34m
Sun 11/229:35 pm -
2 stops14h 43m
Deal found 9/25![Delta logo]()
$708
This Southwest deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/95:45 am -
1 stop11h 55m
Mon 11/169:30 pm -
1 stop12h 45m
Deal found 9/29![Southwest logo]()
$612
This Southwest deal was found by Cheapflights users on 9/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/2611:50 am -
2 stops14h 30m
Mon 11/911:15 pm -
2 stops14h 25m
Deal found 9/26![Southwest logo]()
$618
This Delta deal was found by Cheapflights users on 9/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/19:29 am -
2 stops14h 58m
Sun 11/810:05 pm -
2 stops15h 59m
Deal found 9/27![Delta logo]()
$750
This Southwest deal was found by Cheapflights users on 9/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/276:25 am -
1 stop12h 35m
Sun 11/19:25 pm -
2 stops13h 50m
Deal found 9/26![Southwest logo]()
$618
This Delta deal was found by Cheapflights users on 9/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/69:29 am -
2 stops15h 30m
Fri 11/134:25 pm -
1 stop13h 21m
Deal found 9/27![Delta logo]()
$753
This Southwest deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/65:10 am -
1 stop12h 50m
Sat 12/1210:05 pm -
2 stops13h 10m
Deal found 9/28![Southwest logo]()
$626
This Delta deal was found by Cheapflights users on 9/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/99:30 am -
2 stops15h 34m
Thu 11/124:25 pm -
1 stop13h 21m
Deal found 9/26![Delta logo]()
$761
This Southwest deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 1/1310:15 am -
2 stops15h 35m
Wed 1/2011:35 am -
2 stops14h 15m
Deal found 9/28![Southwest logo]()
$643
This Southwest deal was found by Cheapflights users on 9/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/15:50 am -
2 stops14h 25m
Wed 12/911:50 am -
2 stops14h 05m
Deal found 9/27![Southwest logo]()
$645
This Southwest deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/112:00 pm -
2 stops13h 20m
Wed 12/93:15 pm -
1 stop10h 40m
Deal found 9/28![Southwest logo]()
$648
This Southwest deal was found by Cheapflights users on 9/24. Clicking the “Pick Dates” 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 11/175:20 am -
1 stop11h 35m
Tue 12/111:20 pm -
1 stop14h 05m
Deal found 9/24![Southwest logo]()
$651
This Southwest deal was found by Cheapflights users on 9/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/135:25 am -
1 stop12h 15m
Mon 11/239:30 pm -
2 stops13h 00m
Deal found 9/25![Southwest logo]()
$670
This Delta deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/206:00 am -
1 stop12h 29m
Sat 12/55:59 pm -
1 stop10h 56m
Deal found 9/28![Delta logo]()
$1,214
This Southwest deal was found by Cheapflights users on 9/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/145:05 am -
2 stops17h 05m
Mon 11/239:30 pm -
2 stops13h 00m
Deal found 9/25![Southwest logo]()
$675
This Delta deal was found by Cheapflights users on 9/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/19:37 am -
2 stops14h 53m
Wed 12/98:35 pm -
2 stops15h 41m
Deal found 9/27![Delta logo]()
$1,251
This Southwest deal was found by Cheapflights users on 9/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/85:50 am -
1 stop12h 10m
Sun 12/139:00 am -
1 stop16h 45m
Deal found 9/27![Southwest logo]()
$694
This Southwest deal was found by Cheapflights users on 9/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 1/1110:15 am -
2 stops15h 35m
Sat 1/166:55 pm -
2 stops13h 40m
Deal found 9/26![Southwest logo]()
$704
This Southwest deal was found by Cheapflights users on 9/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/25:50 am -
1 stop11h 20m
Wed 12/99:25 pm -
1 stop12h 45m
Deal found 9/25![Southwest logo]()
$714
This Southwest deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/1410:15 am -
2 stops15h 35m
Thu 1/216:55 pm -
2 stops13h 40m
Deal found 9/29![Southwest logo]()
$719
Last-minute flights from Midway to HawaiiDiscover last-minute flight deals from Midway to Hawaii. Data last updated September 29, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Hawaii. Data last updated September 29, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/66:05 am -
1 stop11h 30m
Tue 10/1312:15 pm -
1 stop12h 40m
Deal found 9/28![Southwest logo]()
$474
This Southwest deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/195:10 am -
1 stop12h 25m
Mon 10/2612:15 pm -
1 stop12h 40m
Deal found 9/28![Southwest logo]()
$494
This Southwest deal was found by Cheapflights users on 9/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/206:05 am -
1 stop11h 35m
Tue 10/279:55 pm -
1 stop14h 10m
Deal found 9/27![Southwest logo]()
$570
This Delta deal was found by Cheapflights users on 9/24. Clicking the “Pick Dates” 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 10/249:29 am -
2 stops14h 45m
Sat 10/319:45 pm -
2 stops16h 15m
Deal found 9/24![Delta logo]()
$551
This Southwest deal was found by Cheapflights users on 9/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/255:20 am -
1 stop12h 15m
Sun 11/14:05 pm -
1 stop15h 30m
Deal found 9/25![Southwest logo]()
$544
This Southwest deal was found by Cheapflights users on 9/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/265:10 am -
1 stop12h 25m
Mon 11/24:05 pm -
1 stop16h 25m
Deal found 9/26![Southwest logo]()
$489
This Southwest deal was found by Cheapflights users on 9/24. Clicking the “Pick Dates” 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 10/265:40 am -
1 stop12h 35m
Mon 11/98:15 am -
1 stop16h 45m
Deal found 9/24![Southwest logo]()
$562
This Southwest deal was found by Cheapflights users on 9/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/265:40 am -
1 stop12h 35m
Tue 11/103:15 pm -
1 stop10h 40m
Deal found 9/25![Southwest logo]()
$570
This Southwest deal was found by Cheapflights users on 9/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/276:55 am -
2 stops19h 30m
Tue 11/310:15 pm -
2 stops15h 05m
Deal found 9/27![Southwest logo]()
$572
This Southwest deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/295:10 am -
1 stop12h 25m
Thu 11/59:30 pm -
1 stop10h 20m
Deal found 9/29![Southwest logo]()
$527
This Delta deal was found by Cheapflights users on 9/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/319:29 am -
2 stops14h 45m
Sun 11/810:51 pm -
2 stops15h 13m
Deal found 9/27![Delta logo]()
$435
This Southwest deal was found by Cheapflights users on 9/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/316:35 am -
1 stop11h 00m
Sun 11/811:50 am -
2 stops14h 05m
Deal found 9/27![Southwest logo]()
$530
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 September 29, 2026.
Search for one-way flight options from Midway to Hawaii. Find affordable one-way fares based on user searches. Data last updated September 29, 2026.
This Southwest deal was found by Cheapflights users on 9/24. Clicking the “Pick Dates” 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 12/3112:00 am -
Nonstop0h 00m
Deal found 9/24![Southwest logo]()
$212
This Delta deal was found by Cheapflights users on 9/24. Clicking the “Pick Dates” 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 12/69:37 am -
2 stops14h 41m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/24![Delta logo]()
$218
This Southwest deal was found by Cheapflights users on 9/26. Clicking the “Pick Dates ” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/105:20 am -
2 stops13h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/26![Southwest logo]()
$241
This Delta deal was found by Cheapflights users on 9/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/39:29 am -
2 stops14h 58m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/25![Delta logo]()
$241
This Southwest deal was found by Cheapflights users on 9/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/2710:30 am -
1 stop15h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/27![Southwest logo]()
$245
This Southwest deal was found by Cheapflights users on 9/24. Clicking the “Pick Dates” 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 10/205:45 am -
1 stop12h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/24![Southwest logo]()
$269
This Southwest deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/265:10 am -
1 stop12h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/28![Southwest logo]()
$285
This Southwest deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/265:25 am -
1 stop12h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/28![Southwest logo]()
$285
This Delta deal was found by Cheapflights users on 9/24. Clicking the “Pick Dates” 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 12/75:30 pm -
2 stops30h 48m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/24![Delta logo]()
$285
This Southwest deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/276:05 am -
1 stop11h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/28![Southwest logo]()
$285
This Southwest deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/276:25 am -
2 stops13h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/28![Southwest logo]()
$291
This Southwest deal was found by Cheapflights users on 9/25. Clicking the “Pick Dates ” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/2812:05 pm -
2 stops13h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/25![Southwest logo]()
$291
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 September 29, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $435 (Delta) |
One-way from | $212 (Southwest) |
Popular in | June |
Cheapest in | February |
Average price | $815 |
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 September 29, 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
Wed 12/9
5:50 am-1:15 pm
1 stop11h 25m
Lihue
Wed 12/31
12:00 am-4:00 am
Nonstop0h 00m
$212
ChicagoKailua-Kona
MDW Chicago Midway - KOA Kona Intl
MDWKOA
Chicago Midway
Tue 11/3
9:29 am-8:27 pm
2 stops14h 58m
Kona Intl
Wed 12/31
12:00 am-4:00 am
Nonstop0h 00m
$241
ChicagoKahului
MDW Chicago Midway - OGG Kahului
MDWOGG
Chicago Midway
Tue 11/10
5:20 am-2:40 pm
2 stops13h 20m
Kahului
Wed 12/31
12:00 am-4:00 am
Nonstop0h 00m
$241
ChicagoKailua-Kona
MDW Chicago Midway - KOA Kona Intl
MDWKOA
Chicago Midway
Thu 11/12
10:05 am-9:25 pm
2 stops15h 20m
Kona Intl
Wed 12/31
12:00 am-4:00 am
Nonstop0h 00m
$241
ChicagoLihue
MDW Chicago Midway - LIH Lihue
MDWLIH
Chicago Midway
Mon 12/7
5:30 pm-8:18 pm
2 stops30h 48m
Lihue
Wed 12/31
12:00 am-4:00 am
Nonstop0h 00m
$285
ChicagoHilo
MDW Chicago Midway - ITO Hilo Intl
MDWITO
Chicago Midway
Mon 10/26
5:10 am-12:35 pm
1 stop12h 25m
Hilo Intl
Wed 12/31
12:00 am-4:00 am
Nonstop0h 00m
$285
ChicagoHonolulu
MDW Chicago Midway - HNL Honolulu
MDWHNL
Chicago Midway
Mon 12/7
5:20 am-2:00 pm
1 stop12h 40m
Honolulu
Wed 12/31
12:00 am-4:00 am
Nonstop0h 00m
$285
ChicagoHonolulu
MDW Chicago Midway - HNL Honolulu
MDWHNL
Chicago Midway
Sun 10/25
10:25 am-9:25 pm
1 stop16h 00m
Honolulu
Wed 12/31
12:00 am-4:00 am
Nonstop0h 00m
$285
ChicagoKailua-Kona
MDW Chicago Midway - KOA Kona Intl
MDWKOA
Chicago Midway
Tue 10/27
6:05 am-12:40 pm
1 stop11h 35m
Kona Intl
Wed 12/31
12:00 am-4:00 am
Nonstop0h 00m
$285
ChicagoLihue
MDW Chicago Midway - LIH Lihue
MDWLIH
Chicago Midway
Mon 2/8
5:55 am-4:20 pm
2 stops14h 25m
Lihue
Wed 12/31
12:00 am-4:00 am
Nonstop0h 00m
$288
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-KOA
MDW-HNL
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-KOA
MDW-HNL
MDW-OGG
What is the cheapest month to book a flight from Chicago Midway Airport to Hawaii?
Currently, February is the cheapest month in which you can book a flight from Chicago Midway Airport to Hawaii (average of $637). Flying from Chicago Midway Airport to Hawaii in October is currently the most expensive (average of $1,064). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
Reviews of airlines servicing Hawaii
Get insights into the airlines that provide service to Hawaii. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Hawaii. Reviews last updated September 29, 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.
Crew
8.6
Overall
8.0
Entertainment
7.5
Food
7.0
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Crew
8.6
Overall
8.0
Entertainment
7.5
Food
7.0
Comfort
8.0
Boarding
8.1
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 September 29, 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 September 29, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$556 | Average$812 | FlexibilityNo cancel fee | On-time63% |