$223+ Cheap flights from Chicago (CHI) to The Big Island
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 10/20. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — KOA
Aug 17 — Aug 241
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to The Big Island with Cheapflights
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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 Chicago to The Big IslandExplore the most affordable flight options available from Chicago to The Big Island. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 18, 2026.
Explore the most affordable flight options available from Chicago to The Big Island. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 18, 2026.
This Alaska Airlines deal was found by Cheapflights users on 7/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/252:18 pm
ORD
- KOA
1 stop29h 30m
Alaska Airlines
Thu 8/2710:35 am
KOA
- ORD
1 stop21h 47m
Alaska Airlines
Deal found 7/17![Alaska Airlines logo]()
$433
This Delta deal was found by Cheapflights users on 7/17. Clicking the “Pick Dates” 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 8/257:00 am
ORD
- KOA
1 stop15h 35m
Delta
Thu 8/278:42 pm
KOA
- ORD
1 stop15h 18m
Delta
Deal found 7/17![Delta logo]()
$434
This Alaska Airlines deal was found by Cheapflights users on 7/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/252:18 pm
ORD
- KOA
1 stop29h 30m
Multiple Airlines
Thu 8/278:45 pm
KOA
- ORD
2 stops17h 36m
Multiple Airlines
Deal found 7/17![Multiple Airlines logo]()
$439
This American Airlines deal was found by Cheapflights users on 7/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/187:00 am
ORD
- KOA
2 stops14h 15m
American Airlines
Tue 8/259:45 pm
KOA
- ORD
1 stop13h 20m
American Airlines
Deal found 7/16![American Airlines logo]()
$440
This American Airlines deal was found by Cheapflights users on 7/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/1110:35 pm
ORD
- KOA
1 stop20h 23m
American Airlines
Tue 8/183:35 pm
KOA
- ORD
1 stop10h 31m
American Airlines
Deal found 7/17![American Airlines logo]()
$492
This Alaska Airlines deal was found by Cheapflights users on 7/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/76:01 am
ORD
- KOA
1 stop13h 47m
Alaska Airlines
Thu 9/1710:35 am
KOA
- ORD
1 stop21h 47m
Alaska Airlines
Deal found 7/18![Alaska Airlines logo]()
$494
This Alaska Airlines deal was found by Cheapflights users on 7/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/97:25 am
ORD
- KOA
1 stop12h 27m
Multiple Airlines
Mon 11/168:45 pm
KOA
- ORD
2 stops23h 04m
Multiple Airlines
Deal found 7/17![Multiple Airlines logo]()
$495
This Alaska Airlines deal was found by Cheapflights users on 7/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/192:18 pm
ORD
- KOA
1 stop29h 30m
Multiple Airlines
Fri 9/256:00 am
KOA
- ORD
2 stops12h 59m
Multiple Airlines
Deal found 7/18![Multiple Airlines logo]()
$499
This Alaska Airlines deal was found by Cheapflights users on 7/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/76:01 am
ORD
- KOA
1 stop13h 47m
Multiple Airlines
Thu 9/176:00 am
KOA
- ORD
2 stops12h 59m
Multiple Airlines
Deal found 7/18![Multiple Airlines logo]()
$500
This Southwest deal was found by Cheapflights users on 7/17. Clicking the “Pick Dates” 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 8/256:50 am
MDW
- KOA
1 stop10h 50m
Southwest
Thu 8/278:35 pm
KOA
- MDW
2 stops13h 40m
Southwest
Deal found 7/17![Southwest logo]()
$500
This American Airlines deal was found by Cheapflights users on 7/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/26:00 am
ORD
- KOA
2 stops15h 15m
American Airlines
Tue 11/39:45 pm
KOA
- ORD
1 stop10h 14m
American Airlines
Deal found 7/16![American Airlines logo]()
$515
This Southwest deal was found by Cheapflights users on 7/17. Clicking the “Pick Dates” 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
MDW
- KOA
2 stops12h 55m
Southwest
Tue 10/278:35 pm
KOA
- MDW
1 stop10h 00m
Southwest
Deal found 7/17![Southwest logo]()
$530
Best flights from Chicago to The Big IslandDiscover carefully curated flight deals from Chicago to The Big Island that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 18, 2026.
Discover carefully curated flight deals from Chicago to The Big Island that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 18, 2026.
This Delta deal was found by Cheapflights users on 7/17. Clicking the “Pick Dates” 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 8/257:00 am
ORD
- KOA
1 stop15h 35m
Delta
Thu 8/278:42 pm
KOA
- ORD
1 stop15h 18m
Delta
Deal found 7/17![Delta logo]()
$434
This Southwest deal was found by Cheapflights users on 7/17. Clicking the “Pick Dates” 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
MDW
- KOA
2 stops12h 55m
Southwest
Tue 10/278:35 pm
KOA
- MDW
1 stop10h 00m
Southwest
Deal found 7/17![Southwest logo]()
$530
This Alaska Airlines deal was found by Cheapflights users on 7/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/251:03 pm
ORD
- KOA
1 stop29h 21m
Alaska Airlines
Thu 8/2710:35 am
KOA
- ORD
1 stop21h 47m
Alaska Airlines
Deal found 7/15![Alaska Airlines logo]()
$553
This Alaska Airlines deal was found by Cheapflights users on 7/14. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/162:18 pm
ORD
- KOA
2 stops24h 14m
Multiple Airlines
Wed 9/3012:18 pm
KOA
- ORD
2 stops18h 49m
Multiple Airlines
Deal found 7/14![Multiple Airlines logo]()
$559
This United Airlines deal was found by Cheapflights users on 7/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/299:30 am
ORD
- ITO
1 stop17h 24m
United Airlines
Wed 9/306:00 am
ITO
- ORD
2 stops17h 45m
United Airlines
Deal found 7/17![United Airlines logo]()
$807
This Alaska Airlines deal was found by Cheapflights users on 7/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/192:18 pm
ORD
- KOA
2 stops24h 14m
Alaska Airlines
Wed 8/2610:35 am
KOA
- ORD
1 stop21h 47m
Alaska Airlines
Deal found 7/16![Alaska Airlines logo]()
$553
This Southwest deal was found by Cheapflights users on 7/17. Clicking the “Pick Dates” 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 8/206:40 am
MDW
- KOA
1 stop11h 00m
Southwest
Thu 8/278:35 pm
KOA
- MDW
2 stops14h 40m
Southwest
Deal found 7/17![Southwest logo]()
$560
This Delta deal was found by Cheapflights users on 7/13. 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.
Mon 8/249:24 am
MDW
- KOA
2 stops14h 53m
Delta
Mon 8/318:42 pm
KOA
- MDW
2 stops16h 19m
Delta
Deal found 7/13![Delta logo]()
$573
This Alaska Airlines deal was found by Cheapflights users on 7/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/297:20 am
ORD
- KOA
2 stops14h 53m
Multiple Airlines
Wed 9/301:28 pm
KOA
- ORD
2 stops17h 39m
Multiple Airlines
Deal found 7/17![Multiple Airlines logo]()
$576
This Southwest deal was found by Cheapflights users on 7/14. 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 9/168:50 pm
MDW
- KOA
2 stops20h 35m
Southwest
Wed 9/3010:00 am
KOA
- MDW
1 stop14h 45m
Southwest
Deal found 7/14![Southwest logo]()
$565
This Alaska Airlines deal was found by Cheapflights users on 7/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/287:20 am
ORD
- KOA
2 stops15h 56m
Multiple Airlines
Sun 11/16:00 am
KOA
- ORD
2 stops13h 49m
Multiple Airlines
Deal found 7/17![Multiple Airlines logo]()
$585
This Alaska Airlines deal was found by Cheapflights users on 7/13. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/248:17 pm
ORD
- KOA
1 stop23h 31m
Alaska Airlines
Mon 8/3110:35 am
KOA
- ORD
1 stop21h 47m
Alaska Airlines
Deal found 7/13![Alaska Airlines logo]()
$603
This Delta deal was found by Cheapflights users on 7/17. Clicking the “Pick Dates” 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 8/207:48 am
ORD
- KOA
2 stops16h 29m
Delta
Thu 8/2710:05 pm
KOA
- ORD
2 stops15h 14m
Delta
Deal found 7/17![Delta logo]()
$605
This Kissandfly.com deal was found by Cheapflights users on 7/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/299:20 am
ORD
- MUE
1 stop14h 52m
Southern / Mokulele
Sat 9/57:17 am
MUE
- ORD
1 stop16h 43m
Southern / Mokulele
Deal found 7/15![Southern / Mokulele logo]()
$1,360
This Southwest deal was found by Cheapflights users on 7/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/238:20 pm
MDW
- ITO
2 stops21h 15m
Southwest
Thu 10/156:00 am
ITO
- MDW
2 stops13h 30m
Southwest
Deal found 7/16![Southwest logo]()
$570
This Expedia deal was found by Cheapflights users on 7/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/286:01 am
ORD
- ITO
2 stops19h 12m
Multiple Airlines
Tue 9/14:44 pm
ITO
- ORD
2 stops21h 37m
Multiple Airlines
Deal found 7/17![Multiple Airlines logo]()
$595
This Southwest deal was found by Cheapflights users on 7/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/226:55 am
MDW
- KOA
1 stop10h 45m
Southwest
Fri 8/288:35 pm
KOA
- MDW
1 stop12h 35m
Southwest
Deal found 7/17![Southwest logo]()
$604
This Alaska Airlines deal was found by Cheapflights users on 7/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/297:20 am
ORD
- ITO
2 stops16h 52m
Multiple Airlines
Wed 9/306:00 am
ITO
- ORD
2 stops12h 59m
Multiple Airlines
Deal found 7/15![Multiple Airlines logo]()
$614
This Southwest deal was found by Cheapflights users on 7/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/176:40 am
MDW
- ITO
1 stop10h 55m
Southwest
Mon 8/248:45 pm
ITO
- MDW
1 stop10h 10m
Southwest
Deal found 7/16![Southwest logo]()
$614
This Alaska Airlines deal was found by Cheapflights users on 7/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/157:20 am
ORD
- KOA
1 stop12h 26m
Multiple Airlines
Thu 10/227:15 pm
KOA
- ORD
2 stops18h 05m
Multiple Airlines
Deal found 7/16![Multiple Airlines logo]()
$620
This Southwest deal was found by Cheapflights users on 7/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/36:40 am
MDW
- ITO
1 stop10h 55m
Southwest
Thu 9/178:45 pm
ITO
- MDW
2 stops14h 30m
Southwest
Deal found 7/16![Southwest logo]()
$620
This Alaska Airlines deal was found by Cheapflights users on 7/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/248:00 am
ORD
- ITO
2 stops15h 17m
Multiple Airlines
Tue 10/136:49 pm
ITO
- ORD
2 stops18h 31m
Multiple Airlines
Deal found 7/16![Multiple Airlines logo]()
$635
This Southwest deal was found by Cheapflights users on 7/13. 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.
Fri 9/117:10 am
MDW
- KOA
2 stops15h 55m
Southwest
Fri 9/188:35 pm
KOA
- MDW
1 stop10h 30m
Southwest
Deal found 7/13![Southwest logo]()
$620
This Alaska Airlines deal was found by Cheapflights users on 7/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/197:00 pm
ORD
- ITO
2 stops24h 25m
Multiple Airlines
Sat 9/2612:54 pm
ITO
- ORD
2 stops18h 13m
Multiple Airlines
Deal found 7/17![Multiple Airlines logo]()
$655
This Southwest deal was found by Cheapflights users on 7/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/510:05 am
MDW
- KOA
2 stops15h 20m
Southwest
Wed 11/1111:40 am
KOA
- MDW
2 stops14h 15m
Southwest
Deal found 7/16![Southwest logo]()
$625
This Orbitz deal was found by Cheapflights users on 7/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/11:03 pm
ORD
- ITO
2 stops23h 00m
Multiple Airlines
Sun 10/48:45 pm
ITO
- ORD
2 stops22h 14m
Multiple Airlines
Deal found 7/17![Multiple Airlines logo]()
$685
This Southwest deal was found by Cheapflights users on 7/13. 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 8/136:40 am
MDW
- ITO
1 stop10h 55m
Southwest
Thu 8/208:45 pm
ITO
- MDW
1 stop10h 20m
Southwest
Deal found 7/13![Southwest logo]()
$634
This Southwest deal was found by Cheapflights users on 7/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/286:40 am
MDW
- KOA
1 stop11h 00m
Southwest
Fri 9/48:35 pm
KOA
- MDW
1 stop12h 35m
Southwest
Deal found 7/14![Southwest logo]()
$634
This Alaska Airlines deal was found by Cheapflights users on 7/14. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/286:01 am
ORD
- ITO
2 stops16h 25m
Multiple Airlines
Fri 9/46:00 am
ITO
- ORD
2 stops12h 59m
Multiple Airlines
Deal found 7/14![Multiple Airlines logo]()
$726
This Southwest deal was found by Cheapflights users on 7/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/206:55 am
MDW
- KOA
1 stop10h 45m
Southwest
Sat 9/269:45 am
KOA
- MDW
1 stop15h 00m
Southwest
Deal found 7/14![Southwest logo]()
$634
Last-minute flights from Chicago to The Big IslandDiscover last-minute flight deals from Chicago to The Big Island. Data last updated July 18, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to The Big Island. Data last updated July 18, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 7/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/1110:35 pm
ORD
- KOA
1 stop20h 23m
American Airlines
Tue 8/183:35 pm
KOA
- ORD
1 stop10h 31m
American Airlines
Deal found 7/17![American Airlines logo]()
$492
This Delta deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/116:00 am
ORD
- KOA
2 stops18h 17m
Delta
Wed 8/268:42 pm
KOA
- ORD
1 stop11h 41m
Delta
Deal found 7/13![Delta logo]()
$540
This American Airlines deal was found by Cheapflights users on 7/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/187:00 am
ORD
- KOA
2 stops14h 15m
American Airlines
Tue 8/259:45 pm
KOA
- ORD
1 stop13h 20m
American Airlines
Deal found 7/16![American Airlines logo]()
$440
This Delta deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/197:00 am
ORD
- KOA
1 stop15h 35m
Delta
Wed 8/268:42 pm
KOA
- ORD
1 stop11h 41m
Delta
Deal found 7/13![Delta logo]()
$534
This Expedia deal was found by Cheapflights users on 7/13. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/192:18 pm
ORD
- KOA
2 stops24h 14m
Multiple Airlines
Wed 8/267:15 pm
KOA
- ORD
2 stops19h 06m
Multiple Airlines
Deal found 7/13![Multiple Airlines logo]()
$539
This Delta deal was found by Cheapflights users on 7/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/246:00 am
ORD
- KOA
2 stops18h 17m
Delta
Mon 8/3110:05 pm
KOA
- ORD
2 stops18h 28m
Delta
Deal found 7/17![Delta logo]()
$538
This Southwest deal was found by Cheapflights users on 7/13. 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 8/246:15 am
MDW
- KOA
2 stops16h 50m
Southwest
Tue 9/110:00 am
KOA
- MDW
1 stop14h 45m
Southwest
Deal found 7/13![Southwest logo]()
$540
This Delta deal was found by Cheapflights users on 7/13. 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.
Mon 8/249:24 am
MDW
- KOA
2 stops14h 53m
Delta
Tue 9/18:42 pm
KOA
- MDW
2 stops16h 19m
Delta
Deal found 7/13![Delta logo]()
$545
This Alaska Airlines deal was found by Cheapflights users on 7/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/252:18 pm
ORD
- KOA
1 stop29h 30m
Alaska Airlines
Thu 8/2710:35 am
KOA
- ORD
1 stop21h 47m
Alaska Airlines
Deal found 7/17![Alaska Airlines logo]()
$433
This Delta deal was found by Cheapflights users on 7/17. Clicking the “Pick Dates” 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 8/257:00 am
ORD
- KOA
1 stop15h 35m
Delta
Thu 8/278:42 pm
KOA
- ORD
1 stop15h 18m
Delta
Deal found 7/17![Delta logo]()
$434
This Alaska Airlines deal was found by Cheapflights users on 7/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/252:18 pm
ORD
- KOA
1 stop29h 30m
Multiple Airlines
Thu 8/278:45 pm
KOA
- ORD
2 stops17h 36m
Multiple Airlines
Deal found 7/17![Multiple Airlines logo]()
$439
This Southwest deal was found by Cheapflights users on 7/17. Clicking the “Pick Dates” 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 8/256:50 am
MDW
- KOA
1 stop10h 50m
Southwest
Thu 8/278:35 pm
KOA
- MDW
2 stops13h 40m
Southwest
Deal found 7/17![Southwest logo]()
$500
One-way flights from Chicago to The Big IslandSearch for one-way flight options from Chicago to The Big Island. Find affordable one-way fares based on user searches. Data last updated July 18, 2026.
Search for one-way flight options from Chicago to The Big Island. Find affordable one-way fares based on user searches. Data last updated July 18, 2026.
This Booking.com deal was found by Cheapflights users on 7/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/207:49 pm
ORD
- KOA
1 stop23h 57m
Alaska Airlines
Deal found 7/17![Alaska Airlines logo]()
$223
This Delta deal was found by Cheapflights users on 7/13. 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.
Sun 8/167:00 am
ORD
- KOA
1 stop15h 35m
Delta
Deal found 7/13![Delta logo]()
$267
This American Airlines deal was found by Cheapflights users on 7/13. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/128:20 am
ORD
- KOA
2 stops12h 55m
American Airlines
Deal found 7/13![American Airlines logo]()
$273
This American Airlines deal was found by Cheapflights users on 7/14. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/165:00 am
ORD
- KOA
1 stop13h 58m
American Airlines
Deal found 7/14![American Airlines logo]()
$277
This Expedia deal was found by Cheapflights users on 7/13. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/52:54 pm
ORD
- KOA
1 stop28h 56m
Alaska Airlines
Deal found 7/13![Alaska Airlines logo]()
$282
This Expedia deal was found by Cheapflights users on 7/13. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/176:20 am
ORD
- KOA
2 stops20h 30m
Multiple Airlines
Deal found 7/13![Multiple Airlines logo]()
$283
This Booking.com deal was found by Cheapflights users on 7/14. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/58:42 pm
ORD
- KOA
2 stops21h 24m
Multiple Airlines
Deal found 7/14![Multiple Airlines logo]()
$293
This Delta deal was found by Cheapflights users on 7/14. 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.
Thu 11/127:35 am
ORD
- KOA
1 stop15h 04m
Delta
Deal found 7/14![Delta logo]()
$301
This Alaska Airlines deal was found by Cheapflights users on 7/14. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/122:25 pm
ORD
- KOA
2 stops24h 09m
Alaska Airlines
Deal found 7/14![Alaska Airlines logo]()
$308
This American Airlines deal was found by Cheapflights users on 7/13. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/1510:35 pm
ORD
- KOA
1 stop20h 23m
American Airlines
Deal found 7/13![American Airlines logo]()
$325
This American Airlines deal was found by Cheapflights users on 7/13. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/45:00 am
ORD
- KOA
1 stop14h 03m
American Airlines
Deal found 7/13![American Airlines logo]()
$327
This Alaska Airlines deal was found by Cheapflights users on 7/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/308:17 pm
ORD
- ITO
2 stops25h 41m
Multiple Airlines
Deal found 7/16![Multiple Airlines logo]()
$368
Find flight deals from Chicago to The Big Island
Keep the following information in mind while searching for Chicago to The Big Island flight deals. Data was last updated July 18, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $433 (Alaska Airlines) |
One-way from | $223 (Booking.com) |
Popular in | December |
Cheapest in | January |
Average price | $864 |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to The Big Island 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 July 18, 2026.
Use the filters below to find and compare flights from Chicago to The Big Island that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoKailua-Kona
ORD - KOA
ORDKOA
Chicago O'Hare Intl
Tue 8/25
7:00 am-5:35 pm
1 stop15h 35m
Kona Intl
Thu 8/27
8:42 pm-5:00 pm
1 stop15h 18m
$434
ChicagoKailua-Kona
MDW - KOA
MDWKOA
Chicago Midway
Wed 10/21
10:15 am-6:10 pm
2 stops12h 55m
Kona Intl
Tue 10/27
8:35 pm-11:35 am
1 stop10h 00m
$530
ChicagoKailua-Kona
ORD - KOA
ORDKOA
Chicago O'Hare Intl
Tue 8/25
1:03 pm-1:24 pm
1 stop29h 21m
Kona Intl
Thu 8/27
10:35 am-1:22 pm
1 stop21h 47m
$553
ChicagoKailua-Kona
ORD - KOA
ORDKOA
Chicago O'Hare Intl
Wed 8/19
2:18 pm-9:32 am
2 stops24h 14m
Kona Intl
Wed 8/26
10:35 am-1:22 pm
1 stop21h 47m
$553
ChicagoKailua-Kona
ORD - KOA
ORDKOA
Chicago O'Hare Intl
Wed 9/16
2:18 pm-9:32 am
2 stops24h 14m
Kona Intl
Wed 9/30
12:18 pm-12:07 pm
2 stops18h 49m
$559
ChicagoKailua-Kona
MDW - KOA
MDWKOA
Chicago Midway
Thu 8/20
6:40 am-12:40 pm
1 stop11h 00m
Kona Intl
Thu 8/27
8:35 pm-4:15 pm
2 stops14h 40m
$560
ChicagoKailua-Kona
MDW - KOA
MDWKOA
Chicago Midway
Wed 9/16
8:50 pm-12:25 pm
2 stops20h 35m
Kona Intl
Wed 9/30
10:00 am-5:45 am
1 stop14h 45m
$565
ChicagoHilo
MDW - ITO
MDWITO
Chicago Midway
Wed 9/23
8:20 pm-12:35 pm
2 stops21h 15m
Hilo Intl
Thu 10/15
6:00 am-12:30 am
2 stops13h 30m
$570
ChicagoKailua-Kona
MDW - KOA
MDWKOA
Chicago Midway
Mon 8/24
9:24 am-7:17 pm
2 stops14h 53m
Kona Intl
Mon 8/31
8:42 pm-6:01 pm
2 stops16h 19m
$573
ChicagoKailua-Kona
ORD - KOA
ORDKOA
Chicago O'Hare Intl
Tue 9/29
7:20 am-5:13 pm
2 stops14h 53m
Kona Intl
Wed 9/30
1:28 pm-12:07 pm
2 stops17h 39m
$576
Showing 1-10 of 56 resultsSorted by cheapest first
Best time to book a flight from Chicago to The Big Island
Have a flexible travel schedule? Discover the best time to fly to The Big Island from Chicago with our price prediction graph.
ORD-KOA
MDW-KOA
ORD-ITO
ORD-MUE
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 to The Big Island
CHI-zzFUI
ORD-KOA
MDW-KOA
ORD-ITO
ORD-MUE
What is the cheapest month to book a flight from Chicago to The Big Island?
Currently, January is the cheapest month in which you can book a flight from Chicago to The Big Island (average of $550). Flying from Chicago to The Big Island in December is currently the most expensive (average of $1,105). 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.
What is the cheapest time of day to fly from CHI to FUI?
Find hourly flight availability from Chicago to The Big Island. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated July 18, 2026.
When flying from Chicago to The Big Island, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.
How far ahead should I book a flight from Chicago to The Big Island?
To ensure you get the cheapest price possible for a flight from Chicago to The Big Island, you should look to book at least 18 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.
Reviews of airlines servicing The Big Island
Get insights into the airlines that provide service to The Big Island. 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 The Big Island. Reviews last updated July 18, 2026.
Read reviews from past customers who have flown Southwest,Alaska Airlines, andDelta from Chicago to The Big Island. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Boarding
8.1
Comfort
8.0
Food
7.0
Crew
8.6
Entertainment
7.5
Overall
8.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Boarding
8.1
Comfort
8.0
Food
7.0
Crew
8.6
Entertainment
7.5
Overall
8.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Boarding
8.1
Comfort
8.0
Food
7.0
Crew
8.6
Entertainment
7.5
Overall
8.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Boarding
8.1
Comfort
8.0
Food
7.0
Crew
8.6
Entertainment
7.5
Overall
8.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Boarding
8.1
Comfort
8.0
Food
7.0
Crew
8.6
Entertainment
7.5
Overall
8.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Boarding
8.1
Comfort
8.0
Food
7.0
Crew
8.6
Entertainment
7.5
Overall
8.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Related info for your journey
Find useful and relevant information for your journey from Chicago to The Big Island. 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 Chicago to The Big Island
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Complete your trip
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Search flights from Chicago to The Big Island by cabin class
Find flights from Chicago to The Big Island, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Chicago and The Big Island flights
Browse other Chicago and The Big Island flight options. Last updated on July 18, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 4 airlines flying from Chicago to The Big Island
Discover the top 4 airlines that operate flights from Chicago to The Big Island. 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 July 18, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$350 | Average$639 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$418 | Average$643 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$445 | Average$687 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$447 | Average$892 | FlexibilityNo cancel fee | On-time69% |