$171+ Cheap flights from Hawaii to Midway (MDW)
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 4/15. Fares are subject to change and may not be available on all flights or dates of travel.
HNL — MDW
Mar 9 — Mar 161
1 adult, Economy
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Find cheap flights from Hawaii to Midway 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 Hawaii to MidwayExplore the most affordable flight options available from Hawaii to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 7, 2026.
Explore the most affordable flight options available from Hawaii to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 7, 2026.
This Southwest deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” 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 4/291:00 pm
HNL
- MDW
1 stop11h 50m
Southwest
Wed 5/610:20 am
MDW
- HNL
1 stop12h 20m
Southwest
Deal found 2/3![Southwest logo]()
$342
This Southwest deal was found by Cheapflights users on 2/4. Clicking the “Pick Dates” 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 3/28:05 am
HNL
- MDW
1 stop12h 20m
Southwest
Mon 3/98:50 am
MDW
- HNL
1 stop17h 20m
Southwest
Deal found 2/4![Southwest logo]()
$391
This Southwest deal was found by Cheapflights users on 2/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/71:00 pm
HNL
- MDW
1 stop11h 50m
Southwest
Sun 5/102:40 pm
MDW
- HNL
1 stop11h 25m
Southwest
Deal found 2/6![Southwest logo]()
$413
This Delta deal was found by Cheapflights users on 2/4. Clicking the “Pick Dates” 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 3/24:45 pm
HNL
- MDW
1 stop12h 09m
Delta
Mon 3/99:30 am
MDW
- HNL
2 stops16h 21m
Delta
Deal found 2/4![Delta logo]()
$438
This Delta deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” 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 4/304:10 pm
HNL
- MDW
2 stops15h 33m
Delta
Wed 5/61:23 pm
MDW
- HNL
2 stops13h 22m
Delta
Deal found 2/3![Delta logo]()
$465
This Delta deal was found by Cheapflights users on 2/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/71:31 pm
HNL
- MDW
2 stops14h 11m
Delta
Sun 5/109:22 am
MDW
- HNL
2 stops16h 49m
Delta
Deal found 2/6![Delta logo]()
$495
This Southwest deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” 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 3/28:10 am
HNL
- MDW
1 stop16h 55m
Southwest
Thu 3/59:30 pm
MDW
- HNL
1 stop17h 30m
Southwest
Deal found 2/3![Southwest logo]()
$502
This Southwest deal was found by Cheapflights users on 2/4. Clicking the “Pick Dates” 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 2/199:15 pm
LIH
- MDW
2 stops17h 10m
Southwest
Mon 2/237:55 am
MDW
- LIH
2 stops14h 20m
Southwest
Deal found 2/4![Southwest logo]()
$605
This Delta deal was found by Cheapflights users on 2/4. Clicking the “Pick Dates” 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 2/69:20 pm
LIH
- MDW
2 stops14h 56m
Delta
Mon 2/99:33 am
MDW
- LIH
2 stops14h 21m
Delta
Deal found 2/4![Delta logo]()
$619
This Delta deal was found by Cheapflights users on 2/5. Clicking the “Pick Dates” 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 2/208:55 pm
KOA
- MDW
2 stops15h 19m
Delta
Tue 2/249:34 am
MDW
- KOA
2 stops14h 05m
Delta
Deal found 2/5![Delta logo]()
$639
This Southwest deal was found by Cheapflights users on 2/6. Clicking the “Pick Dates” 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 8/3110:00 am
OGG
- MDW
1 stop14h 55m
Southwest
Tue 9/1510:15 am
MDW
- OGG
1 stop10h 55m
Southwest
Deal found 2/6![Southwest logo]()
$654
This Southwest deal was found by Cheapflights users on 2/4. Clicking the “Pick Dates” 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 2/57:05 pm
LIH
- MDW
2 stops13h 25m
Southwest
Thu 3/1210:05 am
MDW
- LIH
1 stop11h 05m
Southwest
Deal found 2/4![Southwest logo]()
$659
Best flights from Hawaii to MidwayDiscover carefully curated flight deals from Hawaii to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 7, 2026.
Discover carefully curated flight deals from Hawaii to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 7, 2026.
This Southwest deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” 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 4/291:00 pm
HNL
- MDW
1 stop11h 50m
Southwest
Wed 5/610:20 am
MDW
- HNL
1 stop12h 20m
Southwest
Deal found 2/3![Southwest logo]()
$342
This Delta deal was found by Cheapflights users on 2/4. Clicking the “Pick Dates” 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 3/25:15 pm
HNL
- MDW
2 stops15h 31m
Delta
Mon 3/99:30 am
MDW
- HNL
2 stops16h 21m
Delta
Deal found 2/4![Delta logo]()
$443
This Southwest deal was found by Cheapflights users on 2/4. Clicking the “Pick Dates” 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 3/28:05 am
HNL
- MDW
1 stop12h 20m
Southwest
Mon 3/98:50 am
MDW
- HNL
1 stop17h 20m
Southwest
Deal found 2/4![Southwest logo]()
$391
This Southwest deal was found by Cheapflights users on 2/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/71:00 pm
HNL
- MDW
1 stop11h 50m
Southwest
Sun 5/102:40 pm
MDW
- HNL
1 stop11h 25m
Southwest
Deal found 2/6![Southwest logo]()
$413
This Delta deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” 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 4/304:10 pm
HNL
- MDW
2 stops15h 33m
Delta
Wed 5/61:23 pm
MDW
- HNL
2 stops13h 22m
Delta
Deal found 2/3![Delta logo]()
$465
This Delta deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” 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 4/2912:25 pm
HNL
- MDW
2 stops15h 26m
Delta
Wed 5/69:31 am
MDW
- HNL
2 stops17h 14m
Delta
Deal found 2/3![Delta logo]()
$492
This Southwest deal was found by Cheapflights users on 2/4. Clicking the “Pick Dates” 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 2/199:15 pm
LIH
- MDW
2 stops17h 10m
Southwest
Mon 2/237:55 am
MDW
- LIH
2 stops14h 20m
Southwest
Deal found 2/4![Southwest logo]()
$605
This Delta deal was found by Cheapflights users on 2/5. Clicking the “Pick Dates” 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 2/208:55 pm
KOA
- MDW
2 stops15h 19m
Delta
Tue 2/249:34 am
MDW
- KOA
2 stops14h 05m
Delta
Deal found 2/5![Delta logo]()
$639
This Southwest deal was found by Cheapflights users on 2/4. Clicking the “Pick Dates” 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 3/59:20 pm
LIH
- MDW
1 stop10h 25m
Southwest
Thu 3/1210:05 am
MDW
- LIH
1 stop11h 05m
Southwest
Deal found 2/4![Southwest logo]()
$664
This Delta deal was found by Cheapflights users on 2/6. Clicking the “Pick Dates” 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 2/1810:55 pm
KOA
- MDW
2 stops14h 42m
Delta
Sun 2/229:34 am
MDW
- KOA
2 stops14h 05m
Delta
Deal found 2/6![Delta logo]()
$759
This Southwest deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” 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 3/178:25 pm
KOA
- MDW
2 stops12h 20m
Southwest
Mon 3/2310:05 am
MDW
- KOA
2 stops16h 20m
Southwest
Deal found 2/3![Southwest logo]()
$693
This Southwest deal was found by Cheapflights users on 2/6. Clicking the “Pick Dates” 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 2/217:05 pm
LIH
- MDW
2 stops12h 45m
Southwest
Wed 2/258:25 am
MDW
- LIH
2 stops16h 55m
Southwest
Deal found 2/6![Southwest logo]()
$710
This Delta deal was found by Cheapflights users on 2/4. Clicking the “Pick Dates” 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 4/710:15 pm
KOA
- MDW
2 stops14h 39m
Delta
Sun 4/126:00 am
MDW
- KOA
2 stops18h 16m
Delta
Deal found 2/4![Delta logo]()
$858
This Southwest deal was found by Cheapflights users on 2/4. Clicking the “Pick Dates” 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 2/209:35 pm
OGG
- MDW
1 stop11h 55m
Southwest
Tue 2/245:05 am
MDW
- OGG
1 stop11h 45m
Southwest
Deal found 2/4![Southwest logo]()
$714
This Southwest deal was found by Cheapflights users on 2/4. Clicking the “Pick Dates” 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 2/199:25 pm
OGG
- MDW
1 stop13h 40m
Southwest
Mon 2/238:10 am
MDW
- OGG
1 stop12h 15m
Southwest
Deal found 2/4![Southwest logo]()
$714
This Southwest deal was found by Cheapflights users on 2/5. Clicking the “Pick Dates” 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 2/2810:00 am
KOA
- MDW
2 stops15h 05m
Southwest
Sat 3/710:05 am
MDW
- KOA
2 stops13h 00m
Southwest
Deal found 2/5![Southwest logo]()
$725
This Southwest deal was found by Cheapflights users on 2/5. Clicking the “Pick Dates” 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 2/209:25 pm
KOA
- MDW
2 stops13h 05m
Southwest
Tue 2/246:10 am
MDW
- KOA
1 stop11h 35m
Southwest
Deal found 2/5![Southwest logo]()
$752
This Delta deal was found by Cheapflights users on 2/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/228:31 pm
LIH
- MDW
2 stops16h 43m
Delta
Sun 5/319:23 am
MDW
- LIH
2 stops13h 17m
Delta
Deal found 2/4![Delta logo]()
$1,175
This Southwest deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” 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 3/1510:00 am
KOA
- MDW
1 stop14h 45m
Southwest
Mon 3/2310:05 am
MDW
- KOA
2 stops16h 20m
Southwest
Deal found 2/3![Southwest logo]()
$820
This Southwest deal was found by Cheapflights users on 2/6. Clicking the “Pick Dates” 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 6/197:10 pm
LIH
- MDW
2 stops12h 10m
Southwest
Mon 6/2210:10 am
MDW
- LIH
1 stop11h 00m
Southwest
Deal found 2/6![Southwest logo]()
$990
Last-minute flights from Hawaii to MidwayDiscover last-minute flight deals from Hawaii to Midway. Data last updated February 7, 2026 and is based on user searches.
Discover last-minute flight deals from Hawaii to Midway. Data last updated February 7, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 2/4. Clicking the “Pick Dates” 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 2/69:20 pm
LIH
- MDW
2 stops14h 56m
Delta
Mon 2/99:33 am
MDW
- LIH
2 stops14h 21m
Delta
Deal found 2/4![Delta logo]()
$619
This Southwest deal was found by Cheapflights users on 2/6. Clicking the “Pick Dates” 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 2/109:30 pm
HNL
- MDW
1 stop15h 05m
Southwest
Thu 3/128:50 am
MDW
- HNL
1 stop17h 20m
Southwest
Deal found 2/6![Southwest logo]()
$628
This Southwest deal was found by Cheapflights users on 2/5. Clicking the “Pick Dates” 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 2/189:55 pm
HNL
- MDW
1 stop15h 10m
Southwest
Thu 2/2610:15 pm
MDW
- HNL
1 stop17h 00m
Southwest
Deal found 2/5![Southwest logo]()
$577
This Southwest deal was found by Cheapflights users on 2/4. Clicking the “Pick Dates” 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 2/199:15 pm
LIH
- MDW
2 stops17h 10m
Southwest
Mon 2/237:55 am
MDW
- LIH
2 stops14h 20m
Southwest
Deal found 2/4![Southwest logo]()
$605
This Delta deal was found by Cheapflights users on 2/5. Clicking the “Pick Dates” 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 2/208:55 pm
KOA
- MDW
2 stops15h 19m
Delta
Tue 2/249:34 am
MDW
- KOA
2 stops14h 05m
Delta
Deal found 2/5![Delta logo]()
$639
This Southwest deal was found by Cheapflights users on 2/4. Clicking the “Pick Dates” 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 3/28:05 am
HNL
- MDW
1 stop12h 20m
Southwest
Mon 3/98:50 am
MDW
- HNL
1 stop17h 20m
Southwest
Deal found 2/4![Southwest logo]()
$391
This Delta deal was found by Cheapflights users on 2/4. Clicking the “Pick Dates” 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 3/24:45 pm
HNL
- MDW
1 stop12h 09m
Delta
Mon 3/99:30 am
MDW
- HNL
2 stops16h 21m
Delta
Deal found 2/4![Delta logo]()
$438
This Southwest deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” 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 3/28:10 am
HNL
- MDW
1 stop16h 55m
Southwest
Thu 3/59:30 pm
MDW
- HNL
1 stop17h 30m
Southwest
Deal found 2/3![Southwest logo]()
$502
This Southwest deal was found by Cheapflights users on 2/4. Clicking the “Pick Dates” 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 3/59:20 pm
LIH
- MDW
1 stop10h 25m
Southwest
Thu 3/1210:05 am
MDW
- LIH
1 stop11h 05m
Southwest
Deal found 2/4![Southwest logo]()
$664
This Southwest deal was found by Cheapflights users on 2/5. Clicking the “Pick Dates” 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 3/612:55 pm
HNL
- MDW
1 stop13h 00m
Southwest
Fri 3/139:30 pm
MDW
- HNL
1 stop17h 30m
Southwest
Deal found 2/5![Southwest logo]()
$618
This Southwest deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” 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 3/1311:55 am
HNL
- MDW
1 stop13h 00m
Southwest
Mon 3/169:30 pm
MDW
- HNL
1 stop17h 30m
Southwest
Deal found 2/3![Southwest logo]()
$542
This Southwest deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” 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 3/178:25 pm
KOA
- MDW
2 stops12h 20m
Southwest
Mon 3/2310:05 am
MDW
- KOA
2 stops16h 20m
Southwest
Deal found 2/3![Southwest logo]()
$693
One-way flights from Hawaii to MidwaySearch for one-way flight options from Hawaii to Midway. Find affordable one-way fares based on user searches. Data last updated February 7, 2026.
Search for one-way flight options from Hawaii to Midway. Find affordable one-way fares based on user searches. Data last updated February 7, 2026.
This Southwest deal was found by Cheapflights users on 2/5. Clicking the “Pick Dates” 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 2/278:05 am
HNL
- MDW
1 stop12h 30m
Southwest
Deal found 2/5![Southwest logo]()
$171
This Delta deal was found by Cheapflights users on 2/4. Clicking the “Pick Dates” 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 3/104:00 pm
OGG
- MDW
1 stop12h 56m
Delta
Deal found 2/4![Delta logo]()
$211
This Delta deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” 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 2/271:55 pm
HNL
- MDW
2 stops17h 08m
Delta
Deal found 2/2![Delta logo]()
$218
This Delta deal was found by Cheapflights users on 2/4. Clicking the “Pick Dates” 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 3/24:45 pm
HNL
- MDW
1 stop12h 09m
Delta
Deal found 2/4![Delta logo]()
$220
This Delta deal was found by Cheapflights users on 2/4. Clicking the “Pick Dates” 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 3/234:20 pm
HNL
- MDW
2 stops15h 09m
Delta
Deal found 2/4![Delta logo]()
$226
This Kiwi.com deal was found by Cheapflights users on 2/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/52:54 pm
LIH
- MDW
2 stops51h 30m
Multiple Airlines
Deal found 2/4![Multiple Airlines logo]()
$229
This Kiwi.com deal was found by Cheapflights users on 2/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/171:01 pm
HNL
- MDW
3 stops52h 44m
Multiple Airlines
Deal found 2/4![Multiple Airlines logo]()
$239
This Delta deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” 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 4/143:15 pm
HNL
- MDW
1 stop12h 32m
Delta
Deal found 2/3![Delta logo]()
$242
This Kiwi.com deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/169:40 pm
HNL
- MDW
3 stops43h 39m
Multiple Airlines
Deal found 2/3![Multiple Airlines logo]()
$249
This Southwest deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” 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 3/18:05 am
HNL
- MDW
1 stop12h 30m
Southwest
Deal found 2/3![Southwest logo]()
$251
This Kiwi.com deal was found by Cheapflights users on 2/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/109:28 am
OGG
- MDW
3 stops31h 51m
Multiple Airlines
Deal found 2/4![Multiple Airlines logo]()
$252
This Kiwi.com deal was found by Cheapflights users on 2/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/29:40 pm
HNL
- MDW
3 stops41h 27m
Multiple Airlines
Deal found 2/4![Multiple Airlines logo]()
$257
Find flight deals from Hawaii to Midway
Keep the following information in mind while searching for Hawaii to Midway flight deals. Data was last updated February 7, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $391 (Southwest) |
One-way from | $171 (Southwest) |
Popular in | July |
Cheapest in | February |
Average price | $471 |
Cheapflights Fare Finder
Customize your flight search to find flights from Hawaii to Midway 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 February 7, 2026.
Use the filters below to find and compare flights from Hawaii to Chicago Midway Airport that are best for you.
Fly from
Hawaii
Fly to
Midway
Route
Depart
Return
Price
HonoluluChicago
HNL - MDW
HNLMDW
Honolulu
Wed 4/29
1:00 pm-5:50 am
1 stop11h 50m
Chicago Midway
Wed 5/6
10:20 am-5:40 pm
1 stop12h 20m
$342
HonoluluChicago
HNL - MDW
HNLMDW
Honolulu
Mon 3/2
8:05 am-12:25 am
1 stop12h 20m
Chicago Midway
Mon 3/9
8:50 am-9:10 pm
1 stop17h 20m
$391
HonoluluChicago
HNL - MDW
HNLMDW
Honolulu
Thu 5/7
1:00 pm-5:50 am
1 stop11h 50m
Chicago Midway
Sun 5/10
2:40 pm-9:05 pm
1 stop11h 25m
$413
HonoluluChicago
HNL - MDW
HNLMDW
Honolulu
Mon 3/2
5:15 pm-12:46 pm
2 stops15h 31m
Chicago Midway
Mon 3/9
9:30 am-8:51 pm
2 stops16h 21m
$443
HonoluluChicago
HNL - MDW
HNLMDW
Honolulu
Thu 4/30
4:10 pm-12:43 pm
2 stops15h 33m
Chicago Midway
Wed 5/6
1:23 pm-9:45 pm
2 stops13h 22m
$465
HonoluluChicago
HNL - MDW
HNLMDW
Honolulu
Wed 4/29
12:25 pm-8:51 am
2 stops15h 26m
Chicago Midway
Wed 5/6
9:31 am-9:45 pm
2 stops17h 14m
$492
LihueChicago
LIH - MDW
LIHMDW
Lihue
Thu 2/19
9:15 pm-6:25 pm
2 stops17h 10m
Chicago Midway
Mon 2/23
7:55 am-6:15 pm
2 stops14h 20m
$605
Kailua-KonaChicago
KOA - MDW
KOAMDW
Kona Intl
Fri 2/20
8:55 pm-4:14 pm
2 stops15h 19m
Chicago Midway
Tue 2/24
9:34 am-7:39 pm
2 stops14h 05m
$639
LihueChicago
LIH - MDW
LIHMDW
Lihue
Thu 3/5
9:20 pm-11:45 am
1 stop10h 25m
Chicago Midway
Thu 3/12
10:05 am-4:10 pm
1 stop11h 05m
$664
Kailua-KonaChicago
KOA - MDW
KOAMDW
Kona Intl
Tue 3/17
8:25 pm-1:45 pm
2 stops12h 20m
Chicago Midway
Mon 3/23
10:05 am-9:25 pm
2 stops16h 20m
$693
Showing 1-10 of 50 results
Best time to book a flight from Hawaii to Midway
Have a flexible travel schedule? Discover the best time to fly to Midway from Hawaii with our price prediction graph.
HNL-MDW
LIH-MDW
KOA-MDW
OGG-MDW
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 Hawaii to Chicago Midway Airport
USHI-MDW
HNL-MDW
LIH-MDW
KOA-MDW
OGG-MDW
No data available for this route at this time. Please check back soon.
Related info for your journey
Find useful and relevant information for your journey from Hawaii to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Chicago Midway Airport?
Book flights to Chicago Midway Airport if you plan to visit one of these locationsLansing
Merrillville
Hammond
Porter
Benton Harbor
Browse thousands of different options on Cheapflights for your next trip
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Alternative routes for Hawaii to Midway
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Complete your trip
Complete your trip to Midway by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Hawaii to Midway by cabin class
Find flights from Hawaii to Midway, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Other flights to Midway
Explore flights to Midway departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on February 7, 2026.
Hawaii and Midway flights
Browse other Hawaii and Midway flight options. Last updated on February 7, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Hawaii to Midway flights
Consider these flights traveling from Hawaii to Midway.
Top airline flying from Hawaii to Midway
Discover the top airline that operate flights from Hawaii to Midway. 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 February 7, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$581 | Average$783 | FlexibilityNo cancel fee | On-time63% |