$173+ 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 3/2. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — KOA
Mar 13 — Mar 201
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
Find cheap flights from Chicago to The Big Island 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
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Chicago to The Big Island
Cheapest
Best
Last-minute
One-way
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 February 11, 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 February 11, 2026.
This Orbitz deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/117:59 pm
ORD
- KOA
1 stop23h 57m
Alaska Airlines
Tue 5/1910:36 am
KOA
- ORD
1 stop23h 11m
Alaska Airlines
Deal found 2/9![Alaska Airlines logo]()
$421
This Alaska Airlines deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” 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 3/23:07 pm
ORD
- KOA
1 stop28h 46m
Alaska Airlines
Wed 3/410:17 pm
KOA
- ORD
1 stop11h 54m
Alaska Airlines
Deal found 2/8![Alaska Airlines logo]()
$422
This Delta deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/127:10 am
ORD
- KOA
1 stop15h 32m
Delta
Tue 5/198:55 pm
KOA
- ORD
1 stop11h 38m
Delta
Deal found 2/9![Delta logo]()
$424
This Alaska Airlines deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” 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 3/23:07 pm
ORD
- KOA
1 stop28h 46m
Multiple Airlines
Wed 3/49:01 pm
KOA
- ORD
2 stops15h 32m
Multiple Airlines
Deal found 2/8![Multiple Airlines logo]()
$428
This Expedia deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/33:07 pm
ORD
- KOA
2 stops27h 04m
Multiple Airlines
Tue 3/1712:10 pm
KOA
- ORD
1 stop21h 11m
Multiple Airlines
Deal found 2/9![Multiple Airlines logo]()
$429
This Alaska Airlines deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/107:00 am
ORD
- KOA
1 stop14h 13m
Alaska Airlines
Tue 3/1712:10 pm
KOA
- ORD
1 stop21h 11m
Alaska Airlines
Deal found 2/9![Alaska Airlines logo]()
$432
This Alaska Airlines deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/97:00 am
ORD
- KOA
1 stop14h 13m
Alaska Airlines
Mon 3/169:17 pm
KOA
- ORD
1 stop11h 54m
Alaska Airlines
Deal found 2/10![Alaska Airlines logo]()
$435
This Alaska Airlines deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/43:07 pm
ORD
- KOA
2 stops27h 04m
Multiple Airlines
Mon 3/91:56 pm
KOA
- ORD
2 stops20h 02m
Multiple Airlines
Deal found 2/11![Multiple Airlines logo]()
$437
This Southwest deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” 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
MDW
- KOA
2 stops17h 10m
Southwest
Wed 3/47:00 pm
KOA
- MDW
2 stops13h 30m
Southwest
Deal found 2/8![Southwest logo]()
$495
This Delta deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/99:35 am
MDW
- KOA
2 stops14h 02m
Delta
Mon 3/1610:15 pm
KOA
- MDW
2 stops14h 39m
Delta
Deal found 2/10![Delta logo]()
$497
This Alaska Airlines deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” 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 3/23:07 pm
ORD
- ITO
2 stops30h 34m
Multiple Airlines
Wed 3/46:44 pm
ITO
- ORD
2 stops16h 14m
Multiple Airlines
Deal found 2/8![Multiple Airlines logo]()
$500
This Southwest deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/286:10 am
MDW
- KOA
1 stop12h 05m
Southwest
Thu 5/78:25 pm
KOA
- MDW
2 stops12h 55m
Southwest
Deal found 2/9![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 February 11, 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 February 11, 2026.
This Alaska Airlines deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” 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 3/23:07 pm
ORD
- KOA
1 stop28h 46m
Multiple Airlines
Wed 3/49:01 pm
KOA
- ORD
2 stops15h 32m
Multiple Airlines
Deal found 2/8![Multiple Airlines logo]()
$428
This Delta deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/287:15 am
ORD
- KOA
1 stop16h 48m
Delta
Thu 5/78:55 pm
KOA
- ORD
1 stop15h 09m
Delta
Deal found 2/9![Delta logo]()
$434
This Alaska Airlines deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/97:00 am
ORD
- KOA
1 stop14h 13m
Alaska Airlines
Mon 3/169:17 pm
KOA
- ORD
1 stop11h 54m
Alaska Airlines
Deal found 2/10![Alaska Airlines logo]()
$435
This Southwest deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” 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
MDW
- KOA
2 stops17h 10m
Southwest
Wed 3/47:00 pm
KOA
- MDW
2 stops13h 30m
Southwest
Deal found 2/8![Southwest logo]()
$495
This United Airlines deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/71:43 pm
ORD
- ITO
2 stops22h 25m
United Airlines
Mon 5/1110:56 am
ITO
- ORD
2 stops22h 27m
United Airlines
Deal found 2/11![United Airlines logo]()
$605
This Delta deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/77:25 am
ORD
- KOA
1 stop16h 13m
Delta
Wed 4/158:50 pm
KOA
- ORD
1 stop14h 49m
Delta
Deal found 2/10![Delta logo]()
$434
This Alaska Airlines deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/27:00 am
ORD
- KOA
1 stop14h 13m
Alaska Airlines
Wed 3/41:10 pm
KOA
- ORD
1 stop30h 49m
Alaska Airlines
Deal found 2/9![Alaska Airlines logo]()
$442
This Alaska Airlines deal was found by Cheapflights users on 2/7. Clicking the “Pick Dates” 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 3/23:07 pm
ORD
- ITO
2 stops30h 34m
Multiple Airlines
Wed 3/46:44 pm
ITO
- ORD
2 stops25h 15m
Multiple Airlines
Deal found 2/7![Multiple Airlines logo]()
$455
This Delta deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” 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 3/97:25 am
ORD
- KOA
1 stop16h 12m
Delta
Mon 3/2310:15 pm
KOA
- ORD
2 stops18h 19m
Delta
Deal found 2/8![Delta logo]()
$442
This Southwest deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” 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 4/76:10 am
MDW
- KOA
2 stops13h 20m
Southwest
Tue 4/148:25 pm
KOA
- MDW
2 stops12h 50m
Southwest
Deal found 2/8![Southwest logo]()
$538
This Delta deal was found by Cheapflights users on 2/7. Clicking the “Pick Dates” 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 3/97:20 am
ORD
- KOA
2 stops16h 17m
Delta
Mon 3/1610:15 pm
KOA
- ORD
2 stops18h 19m
Delta
Deal found 2/7![Delta logo]()
$447
This Alaska Airlines deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/308:50 am
ORD
- ITO
2 stops16h 38m
Multiple Airlines
Mon 5/46:44 pm
ITO
- ORD
2 stops19h 19m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$546
This United Airlines deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/307:00 am
ORD
- ITO
2 stops19h 33m
United Airlines
Mon 5/46:00 am
ITO
- ORD
2 stops19h 03m
United Airlines
Deal found 2/11![United Airlines logo]()
$605
This Southwest deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/286:10 am
MDW
- KOA
1 stop12h 05m
Southwest
Thu 5/78:25 pm
KOA
- MDW
1 stop11h 45m
Southwest
Deal found 2/9![Southwest logo]()
$551
This Delta deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/99:35 am
MDW
- KOA
2 stops14h 02m
Delta
Mon 3/1610:15 pm
KOA
- MDW
2 stops14h 39m
Delta
Deal found 2/10![Delta logo]()
$497
This Southwest deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/115:10 am
MDW
- KOA
2 stops14h 05m
Southwest
Tue 5/1910:00 am
KOA
- MDW
1 stop14h 45m
Southwest
Deal found 2/9![Southwest logo]()
$560
This Alaska Airlines deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” 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 4/102:09 pm
ORD
- ITO
2 stops13h 24m
Multiple Airlines
Thu 4/305:59 pm
ITO
- ORD
2 stops24h 44m
Multiple Airlines
Deal found 2/8![Multiple Airlines logo]()
$565
This Southwest deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/126:10 am
MDW
- KOA
2 stops16h 55m
Southwest
Tue 5/1910:00 am
KOA
- MDW
1 stop14h 45m
Southwest
Deal found 2/9![Southwest logo]()
$560
This Alaska Airlines deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/78:50 am
ORD
- ITO
2 stops17h 43m
Multiple Airlines
Mon 5/115:59 pm
ITO
- ORD
2 stops20h 04m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$577
This Southwest deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/95:00 am
MDW
- KOA
1 stop13h 00m
Southwest
Mon 3/168:25 pm
KOA
- MDW
1 stop13h 25m
Southwest
Deal found 2/10![Southwest logo]()
$569
This Alaska Airlines deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/28:20 am
ORD
- ITO
2 stops37h 21m
Multiple Airlines
Mon 3/97:36 pm
ITO
- ORD
2 stops23h 23m
Multiple Airlines
Deal found 2/9![Multiple Airlines logo]()
$608
This Southwest deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” 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 3/116:30 am
MDW
- KOA
1 stop11h 30m
Southwest
Wed 3/1810:00 am
KOA
- MDW
1 stop14h 45m
Southwest
Deal found 2/8![Southwest logo]()
$571
This Alaska Airlines deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/287:00 am
ORD
- ITO
2 stops17h 23m
Multiple Airlines
Tue 3/31:45 pm
ITO
- ORD
2 stops20h 26m
Multiple Airlines
Deal found 2/9![Multiple Airlines logo]()
$615
This Alaska Airlines deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” 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 3/316:00 am
ORD
- ITO
2 stops16h 27m
Multiple Airlines
Tue 4/79:00 pm
ITO
- ORD
2 stops21h 59m
Multiple Airlines
Deal found 2/8![Multiple Airlines logo]()
$616
This Alaska Airlines deal was found by Cheapflights users on 2/7. Clicking the “Pick Dates” 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 3/37:00 am
ORD
- ITO
2 stops15h 46m
Multiple Airlines
Sat 3/74:39 pm
ITO
- ORD
2 stops15h 32m
Multiple Airlines
Deal found 2/7![Multiple Airlines logo]()
$656
This Southwest deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” 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 5/810:10 am
MDW
- ITO
2 stops16h 35m
Southwest
Tue 5/196:55 pm
ITO
- MDW
2 stops14h 35m
Southwest
Deal found 2/8![Southwest logo]()
$750
This Southwest deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” 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 4/135:25 am
MDW
- ITO
2 stops14h 05m
Southwest
Sun 4/196:00 am
ITO
- MDW
2 stops13h 25m
Southwest
Deal found 2/8![Southwest logo]()
$760
This Expedia deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” 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 2/283:07 pm
ORD
- MUE
2 stops19h 46m
Multiple Airlines
Sun 3/19:10 pm
MUE
- ORD
2 stops13h 48m
Multiple Airlines
Deal found 2/8![Multiple Airlines logo]()
$778
This Southwest deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” 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 4/105:25 am
MDW
- ITO
2 stops14h 05m
Southwest
Thu 4/306:55 pm
ITO
- MDW
2 stops12h 40m
Southwest
Deal found 2/8![Southwest logo]()
$795
This Southwest deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” 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 2/227:55 am
MDW
- ITO
2 stops14h 15m
Southwest
Thu 2/266:55 pm
ITO
- MDW
2 stops16h 10m
Southwest
Deal found 2/8![Southwest logo]()
$805
Last-minute flights from Chicago to The Big IslandDiscover last-minute flight deals from Chicago to The Big Island. Data last updated February 11, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to The Big Island. Data last updated February 11, 2026 and is based on user searches.
This Alaska Airlines deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” 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 3/23:07 pm
ORD
- KOA
1 stop28h 46m
Alaska Airlines
Wed 3/410:17 pm
KOA
- ORD
1 stop11h 54m
Alaska Airlines
Deal found 2/8![Alaska Airlines logo]()
$422
This Alaska Airlines deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” 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 3/23:07 pm
ORD
- KOA
1 stop28h 46m
Multiple Airlines
Wed 3/49:01 pm
KOA
- ORD
2 stops15h 32m
Multiple Airlines
Deal found 2/8![Multiple Airlines logo]()
$428
This Alaska Airlines deal was found by Cheapflights users on 2/7. Clicking the “Pick Dates” 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 3/23:07 pm
ORD
- ITO
2 stops30h 34m
Multiple Airlines
Wed 3/46:44 pm
ITO
- ORD
2 stops25h 15m
Multiple Airlines
Deal found 2/7![Multiple Airlines logo]()
$455
This Southwest deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” 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
MDW
- KOA
2 stops17h 10m
Southwest
Wed 3/47:00 pm
KOA
- MDW
2 stops13h 30m
Southwest
Deal found 2/8![Southwest logo]()
$495
This Expedia deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/33:07 pm
ORD
- KOA
2 stops27h 04m
Multiple Airlines
Tue 3/1712:10 pm
KOA
- ORD
1 stop21h 11m
Multiple Airlines
Deal found 2/9![Multiple Airlines logo]()
$429
This Delta deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/37:15 am
ORD
- KOA
2 stops16h 24m
Delta
Tue 3/1010:15 pm
KOA
- ORD
2 stops18h 19m
Delta
Deal found 2/10![Delta logo]()
$445
This Alaska Airlines deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/43:07 pm
ORD
- KOA
2 stops27h 04m
Multiple Airlines
Mon 3/91:56 pm
KOA
- ORD
2 stops20h 02m
Multiple Airlines
Deal found 2/11![Multiple Airlines logo]()
$437
This Alaska Airlines deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/97:00 am
ORD
- KOA
1 stop14h 13m
Alaska Airlines
Mon 3/169:17 pm
KOA
- ORD
1 stop11h 54m
Alaska Airlines
Deal found 2/10![Alaska Airlines logo]()
$435
This Alaska Airlines deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/93:54 pm
ORD
- KOA
2 stops25h 06m
Multiple Airlines
Mon 3/169:17 pm
KOA
- ORD
1 stop11h 54m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$440
This Delta deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/99:35 am
MDW
- KOA
2 stops14h 02m
Delta
Mon 3/1610:15 pm
KOA
- MDW
2 stops14h 39m
Delta
Deal found 2/10![Delta logo]()
$497
This Alaska Airlines deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/107:00 am
ORD
- KOA
1 stop14h 13m
Alaska Airlines
Tue 3/1712:10 pm
KOA
- ORD
1 stop21h 11m
Alaska Airlines
Deal found 2/9![Alaska Airlines logo]()
$432
This Expedia deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/117:40 am
ORD
- KOA
1 stop12h 13m
Alaska Airlines
Tue 3/1712:10 pm
KOA
- ORD
1 stop25h 52m
Alaska Airlines
Deal found 2/10![Alaska Airlines logo]()
$444
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 February 11, 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 February 11, 2026.
This Kiwi.com deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/27:25 pm
MDW
- KOA
3 stops46h 00m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$173
This Alaska Airlines deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/108:20 am
ORD
- KOA
2 stops27h 57m
Multiple Airlines
Deal found 2/9![Multiple Airlines logo]()
$208
This Alaska Airlines deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/107:00 am
ORD
- KOA
1 stop14h 13m
Alaska Airlines
Deal found 2/11![Alaska Airlines logo]()
$211
This Kiwi.com deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/26:51 pm
ORD
- KOA
3 stops39h 35m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$213
This Alaska Airlines deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/72:07 pm
ORD
- KOA
1 stop24h 46m
Alaska Airlines
Deal found 2/9![Alaska Airlines logo]()
$217
This Delta deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/307:15 am
ORD
- KOA
1 stop16h 48m
Delta
Deal found 2/9![Delta logo]()
$224
This Kiwi.com deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/112:56 pm
ORD
- KOA
3 stops52h 29m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$225
This Kiwi.com deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/13:21 pm
MDW
- KOA
3 stops50h 04m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$236
This Expedia deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/117:40 am
ORD
- KOA
1 stop12h 13m
Alaska Airlines
Deal found 2/10![Alaska Airlines logo]()
$242
This Alaska Airlines deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/73:07 pm
ORD
- KOA
2 stops27h 04m
Multiple Airlines
Deal found 2/11![Multiple Airlines logo]()
$244
This Southwest deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/28:10 am
MDW
- KOA
2 stops17h 10m
Southwest
Deal found 2/10![Southwest logo]()
$248
This Southwest deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” 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 5/45:10 am
MDW
- KOA
2 stops14h 20m
Southwest
Deal found 2/8![Southwest logo]()
$291
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 February 11, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $421 (Orbitz) |
One-way from | $173 (Kiwi.com) |
Popular in | December |
Cheapest in | January |
Average price | $648 |
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 February 11, 2026.
Use the filters below to find and compare flights from Chicago to The Big Island that are best for you.
Fly from
Chicago
Fly to
The Big Island
Route
Depart
Return
Price
ChicagoKailua-Kona
ORD - KOA
ORDKOA
Chicago O'Hare Intl
Mon 3/2
3:07 pm-3:53 pm
1 stop28h 46m
Kona Intl
Wed 3/4
9:01 pm-4:33 pm
2 stops15h 32m
$428
ChicagoKailua-Kona
ORD - KOA
ORDKOA
Chicago O'Hare Intl
Tue 4/28
7:15 am-7:03 pm
1 stop16h 48m
Kona Intl
Thu 5/7
8:55 pm-5:04 pm
1 stop15h 09m
$434
ChicagoKailua-Kona
ORD - KOA
ORDKOA
Chicago O'Hare Intl
Tue 4/7
7:25 am-6:38 pm
1 stop16h 13m
Kona Intl
Wed 4/15
8:50 pm-4:39 pm
1 stop14h 49m
$434
ChicagoKailua-Kona
ORD - KOA
ORDKOA
Chicago O'Hare Intl
Mon 3/9
7:00 am-4:13 pm
1 stop14h 13m
Kona Intl
Mon 3/16
9:17 pm-2:11 pm
1 stop11h 54m
$435
ChicagoKailua-Kona
ORD - KOA
ORDKOA
Chicago O'Hare Intl
Mon 3/2
7:00 am-5:13 pm
1 stop14h 13m
Kona Intl
Wed 3/4
1:10 pm-11:59 pm
1 stop30h 49m
$442
ChicagoKailua-Kona
ORD - KOA
ORDKOA
Chicago O'Hare Intl
Mon 3/9
7:25 am-6:37 pm
1 stop16h 12m
Kona Intl
Mon 3/23
10:15 pm-9:34 pm
2 stops18h 19m
$442
ChicagoKailua-Kona
ORD - KOA
ORDKOA
Chicago O'Hare Intl
Mon 3/9
7:20 am-6:37 pm
2 stops16h 17m
Kona Intl
Mon 3/16
10:15 pm-9:34 pm
2 stops18h 19m
$447
ChicagoHilo
ORD - ITO
ORDITO
Chicago O'Hare Intl
Mon 3/2
3:07 pm-5:41 pm
2 stops30h 34m
Hilo Intl
Wed 3/4
6:44 pm-11:59 pm
2 stops25h 15m
$455
ChicagoKailua-Kona
MDW - KOA
MDWKOA
Chicago Midway
Mon 3/2
8:10 am-9:20 pm
2 stops17h 10m
Kona Intl
Wed 3/4
7:00 pm-12:30 pm
2 stops13h 30m
$495
ChicagoKailua-Kona
MDW - KOA
MDWKOA
Chicago Midway
Mon 3/9
9:35 am-6:37 pm
2 stops14h 02m
Kona Intl
Mon 3/16
10:15 pm-5:54 pm
2 stops14h 39m
$497
Showing 1-10 of 48 results
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
MDW-ITO
ORD-MUE
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
MDW-ITO
What is the cheapest month to book a flight from Chicago to The Big Island?
Currently, March is the cheapest month in which you can book a flight from Chicago to The Big Island (average of $371). Flying from Chicago to The Big Island in July is currently the most expensive (average of $668). 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 February 11, 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.
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 February 11, 2026.
Read reviews from past customers who have flown Alaska Airlines, Southwest, and Delta 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.
Overall
8.0
Crew
8.5
Comfort
7.8
Food
7.1
Boarding
8.1
Entertainment
7.0
Reviews
1 / 20
10.0
Excellentrobert,Feb 2026
LAS - SAN
Overall
8.0
Crew
8.5
Comfort
7.8
Food
7.1
Boarding
8.1
Entertainment
7.0
Reviews
1 / 20
10.0
Excellentrobert,Feb 2026
LAS - SAN
Overall
8.0
Crew
8.5
Comfort
7.8
Food
7.1
Boarding
8.1
Entertainment
7.0
Reviews
1 / 20
10.0
Excellentrobert,Feb 2026
LAS - SAN
Overall
8.0
Crew
8.5
Comfort
7.8
Food
7.1
Boarding
8.1
Entertainment
7.0
Reviews
1 / 20
10.0
Excellentrobert,Feb 2026
LAS - SAN
Overall
8.0
Crew
8.5
Comfort
7.8
Food
7.1
Boarding
8.1
Entertainment
7.0
Reviews
1 / 20
10.0
Excellentrobert,Feb 2026
LAS - SAN
Overall
8.0
Crew
8.5
Comfort
7.8
Food
7.1
Boarding
8.1
Entertainment
7.0
Reviews
1 / 20
10.0
Excellentrobert,Feb 2026
LAS - SAN
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.
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
Complete your trip
Flights by cabin class
Other flight options
Popular flights
Alternative routes for Chicago to The Big Island
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to The Big Island by adding a car rental and/or hotel reservation to your travel itinerary.
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 February 11, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 6 airlines flying from Chicago to The Big Island
Discover the top 6 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 February 11, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$265 | Average$574 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$418 | Average$770 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$429 | Average$609 | FlexibilityNo cancel fee | On-time85% | |
| Cheapest$447 | Average$1,086 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$453 | Average$709 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$578 | Average$788 | FlexibilityNo cancel fee | On-time63% |