$212+ Cheap flights from Hawaii to Chicago (CHI)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 1/8. Fares are subject to change and may not be available on all flights or dates of travel.
HNL — CHI
Nov 4 — Nov 111
Round-trip
1 adult, Economy
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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 Hawaii to ChicagoExplore the most affordable flight options available from Hawaii to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 5, 2026.
Explore the most affordable flight options available from Hawaii to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 5, 2026.
This Delta deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” 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 10/169:53 pm -
1 stop14h 00m
Tue 10/2012:50 pm -
1 stop11h 29m
Deal found 9/30![Delta logo]()
$444
This United Airlines deal was found by Cheapflights users on 10/4. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/71:05 pm -
1 stop11h 10m
Fri 10/912:40 pm -
1 stop12h 04m
Deal found 10/4![United Airlines logo]()
$484
This Delta deal was found by Cheapflights users on 10/4. 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.
Wed 10/79:53 pm -
1 stop14h 00m
Fri 10/97:00 am -
2 stops17h 14m
Deal found 10/4![Delta logo]()
$490
This United Airlines deal was found by Cheapflights users on 10/4. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/81:05 pm -
1 stop11h 10m
Fri 10/912:40 pm -
1 stop12h 04m
Deal found 10/4![United Airlines logo]()
$494
This Alaska Airlines deal was found by Cheapflights users on 10/2. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/211:09 pm -
1 stop15h 50m
Mon 11/97:20 am -
1 stop12h 01m
Deal found 10/2![Alaska Airlines logo]()
$498
This Southwest deal was found by Cheapflights users on 10/4. 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 11/98:15 am -
1 stop16h 45m
Mon 11/1610:05 am -
1 stop13h 25m
Deal found 10/4![Southwest logo]()
$506
This Southwest deal was found by Cheapflights users on 10/3. 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 11/210:50 pm -
1 stop14h 25m
Mon 11/97:30 am -
2 stops17h 40m
Deal found 10/3![Southwest logo]()
$512
This Alaska Airlines deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” 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 12/111:15 pm -
1 stop15h 45m
Thu 12/32:13 pm -
1 stop11h 33m
Deal found 9/30![Multiple Airlines logo]()
$548
This Alaska Airlines deal was found by Cheapflights users on 10/4. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/309:10 am -
2 stops15h 30m
Thu 11/57:20 am -
1 stop12h 01m
Deal found 10/4![Multiple Airlines logo]()
$551
This American Airlines deal was found by Cheapflights users on 10/2. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/27:00 pm -
Nonstop8h 27m
Mon 11/910:00 am -
Nonstop9h 18m
Deal found 10/2![American Airlines logo]()
$564
This American Airlines deal was found by Cheapflights users on 10/1. Clicking the “Pick Dates” 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.
Mon 11/237:00 pm -
Nonstop8h 21m
Mon 11/3010:00 am -
Nonstop9h 17m
Deal found 10/1![American Airlines logo]()
$567
This Southwest deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/221:30 pm -
1 stop17h 20m
Tue 10/2710:30 am -
1 stop15h 50m
Deal found 9/30![Southwest logo]()
$570
Best flights from Hawaii to ChicagoDiscover carefully curated flight deals from Hawaii to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 5, 2026.
Discover carefully curated flight deals from Hawaii to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 5, 2026.
This Alaska Airlines deal was found by Cheapflights users on 10/3. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/225:59 pm -
2 stops15h 55m
Tue 3/27:55 pm -
1 stop24h 14m
Deal found 10/3![Multiple Airlines logo]()
$429
This American Airlines deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” 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.
Mon 2/222:15 pm -
1 stop11h 44m
Tue 3/26:48 am -
1 stop13h 12m
Deal found 9/30![American Airlines logo]()
$444
This Delta deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” 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 10/169:53 pm -
1 stop14h 00m
Tue 10/207:35 am -
2 stops16h 44m
Deal found 9/30![Delta logo]()
$450
This Alaska Airlines deal was found by Cheapflights users on 10/4. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/28:10 am -
1 stop11h 49m
Wed 2/32:11 pm -
1 stop11h 57m
Deal found 10/4![Alaska Airlines logo]()
$506
This Southwest deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” 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 2/2511:40 am -
2 stops14h 10m
Mon 3/15:00 am -
1 stop13h 55m
Deal found 9/30![Southwest logo]()
$576
This United Airlines deal was found by Cheapflights users on 10/3. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/221:05 pm -
1 stop11h 10m
Mon 10/2612:42 pm -
1 stop13h 48m
Deal found 10/3![United Airlines logo]()
$594
This Delta deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/2210:45 pm -
2 stops17h 52m
Tue 3/27:35 am -
1 stop14h 45m
Deal found 9/30![Delta logo]()
$480
This Southwest deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/210:50 pm -
1 stop14h 25m
Mon 11/97:25 am -
2 stops17h 40m
Deal found 9/30![Southwest logo]()
$594
This Alaska Airlines deal was found by Cheapflights users on 10/3. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1911:09 pm -
1 stop16h 54m
Mon 11/239:01 pm -
1 stop19h 37m
Deal found 10/3![Multiple Airlines logo]()
$606
This Alaska Airlines deal was found by Cheapflights users on 10/3. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/910:49 pm -
1 stop10h 20m
Wed 11/112:15 pm -
1 stop11h 34m
Deal found 10/3![Alaska Airlines logo]()
$625
This Delta deal was found by Cheapflights users on 10/2. 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.
Thu 10/221:05 pm -
2 stops14h 39m
Tue 10/279:29 am -
2 stops15h 19m
Deal found 10/2![Delta logo]()
$581
This United Airlines deal was found by Cheapflights users on 10/2. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/42:29 pm -
1 stop11h 29m
Fri 11/273:00 pm -
1 stop11h 45m
Deal found 10/2![United Airlines logo]()
$670
This Southwest deal was found by Cheapflights users on 10/3. 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 10/198:10 am -
1 stop11h 30m
Fri 10/235:25 am -
1 stop12h 15m
Deal found 10/3![Southwest logo]()
$612
This Alaska Airlines deal was found by Cheapflights users on 10/3. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/97:41 pm -
2 stops15h 19m
Wed 11/112:15 pm -
1 stop11h 34m
Deal found 10/3![Multiple Airlines logo]()
$631
This Expedia deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” 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.
Sun 11/811:34 am -
1 stop21h 43m
Tue 11/177:20 am -
1 stop12h 32m
Deal found 9/30![Alaska Airlines logo]()
$642
This Delta deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/25:50 pm -
1 stop14h 56m
Mon 11/97:45 am -
1 stop13h 59m
Deal found 9/30![Delta logo]()
$605
This Alaska Airlines deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” 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 11/88:45 pm -
2 stops23h 04m
Tue 11/177:20 am -
1 stop12h 32m
Deal found 9/30![Multiple Airlines logo]()
$634
This American Airlines deal was found by Cheapflights users on 10/3. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/261:51 pm -
1 stop12h 09m
Mon 11/210:00 am -
1 stop11h 47m
Deal found 10/3![American Airlines logo]()
$770
This Southwest deal was found by Cheapflights users on 10/2. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/247:05 pm -
2 stops12h 55m
Tue 3/27:25 am -
1 stop11h 30m
Deal found 10/2![Southwest logo]()
$642
This United Airlines deal was found by Cheapflights users on 10/2. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/188:00 pm -
1 stop10h 28m
Thu 10/226:00 am -
1 stop10h 47m
Deal found 10/2![United Airlines logo]()
$712
This Delta deal was found by Cheapflights users on 10/1. Clicking the “Pick Dates” 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 10/2610:02 pm -
1 stop10h 36m
Tue 11/107:30 am -
1 stop11h 11m
Deal found 10/1![Delta logo]()
$622
This Southwest deal was found by Cheapflights users on 10/2. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/259:30 pm -
2 stops13h 45m
Tue 3/210:15 am -
2 stops15h 10m
Deal found 10/2![Southwest logo]()
$647
This American Airlines deal was found by Cheapflights users on 10/3. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/174:59 pm -
1 stop10h 28m
Sat 12/1211:10 am -
1 stop11h 46m
Deal found 10/3![American Airlines logo]()
$785
This Alaska Airlines deal was found by Cheapflights users on 10/2. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/266:18 pm -
2 stops19h 35m
Mon 11/27:57 pm -
2 stops26h 22m
Deal found 10/2![Multiple Airlines logo]()
$675
This Delta deal was found by Cheapflights users on 10/2. 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.
Thu 11/54:15 pm -
1 stop13h 17m
Sat 11/149:30 am -
2 stops15h 34m
Deal found 10/2![Delta logo]()
$626
This Southwest deal was found by Cheapflights users on 10/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/229:00 am -
1 stop16h 45m
Mon 11/3010:55 pm -
2 stops18h 00m
Deal found 10/1![Southwest logo]()
$653
This Delta deal was found by Cheapflights users on 10/2. 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.
Tue 11/101:35 pm -
2 stops16h 11m
Fri 11/136:00 am -
1 stop12h 40m
Deal found 10/2![Delta logo]()
$626
This Expedia deal was found by Cheapflights users on 10/4. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/18:45 pm -
2 stops18h 14m
Sun 11/87:57 pm -
2 stops26h 22m
Deal found 10/4![Multiple Airlines logo]()
$705
This Southwest deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/168:30 pm -
1 stop10h 00m
Tue 10/206:05 am -
1 stop11h 30m
Deal found 9/30![Southwest logo]()
$655
This Delta deal was found by Cheapflights users on 10/3. 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 11/1010:45 pm -
1 stop10h 52m
Wed 11/187:30 am -
2 stops15h 02m
Deal found 10/3![Delta logo]()
$642
Last-minute flights from Hawaii to ChicagoDiscover last-minute flight deals from Hawaii to Chicago. Data last updated October 5, 2026 and is based on user searches.
Discover last-minute flight deals from Hawaii to Chicago. Data last updated October 5, 2026 and is based on user searches.
This United Airlines deal was found by Cheapflights users on 10/4. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/71:05 pm -
1 stop11h 10m
Fri 10/912:40 pm -
1 stop12h 04m
Deal found 10/4![United Airlines logo]()
$484
This Delta deal was found by Cheapflights users on 10/4. 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.
Wed 10/79:53 pm -
1 stop14h 00m
Fri 10/97:00 am -
2 stops17h 14m
Deal found 10/4![Delta logo]()
$490
This United Airlines deal was found by Cheapflights users on 10/4. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/81:05 pm -
1 stop11h 10m
Fri 10/912:40 pm -
1 stop12h 04m
Deal found 10/4![United Airlines logo]()
$494
This Delta deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” 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 10/169:53 pm -
1 stop14h 00m
Tue 10/2012:50 pm -
1 stop11h 29m
Deal found 9/30![Delta logo]()
$444
This Alaska Airlines deal was found by Cheapflights users on 10/1. Clicking the “Pick Dates” 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 10/2012:10 pm -
1 stop20h 15m
Tue 11/37:20 am -
1 stop12h 01m
Deal found 10/1![Multiple Airlines logo]()
$548
This Southwest deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/221:30 pm -
1 stop17h 20m
Tue 10/2710:30 am -
1 stop15h 50m
Deal found 9/30![Southwest logo]()
$570
This Alaska Airlines deal was found by Cheapflights users on 10/4. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/309:10 am -
2 stops15h 30m
Thu 11/57:20 am -
1 stop12h 01m
Deal found 10/4![Multiple Airlines logo]()
$551
This Alaska Airlines deal was found by Cheapflights users on 10/2. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/211:09 pm -
1 stop15h 50m
Mon 11/97:20 am -
1 stop12h 01m
Deal found 10/2![Alaska Airlines logo]()
$498
This Southwest deal was found by Cheapflights users on 10/3. 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 11/210:50 pm -
1 stop14h 25m
Mon 11/97:30 am -
2 stops17h 40m
Deal found 10/3![Southwest logo]()
$512
This American Airlines deal was found by Cheapflights users on 10/2. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/27:00 pm -
Nonstop8h 27m
Mon 11/910:00 am -
Nonstop9h 18m
Deal found 10/2![American Airlines logo]()
$564
This Southwest deal was found by Cheapflights users on 10/4. 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 11/98:15 am -
1 stop16h 45m
Mon 11/1610:05 am -
1 stop13h 25m
Deal found 10/4![Southwest logo]()
$506
This American Airlines deal was found by Cheapflights users on 10/1. Clicking the “Pick Dates” 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.
Mon 11/237:00 pm -
Nonstop8h 21m
Mon 11/3010:00 am -
Nonstop9h 17m
Deal found 10/1![American Airlines logo]()
$567
One-way flights from Hawaii to ChicagoSearch for one-way flight options from Hawaii to Chicago. Find affordable one-way fares based on user searches. Data last updated October 5, 2026.
Search for one-way flight options from Hawaii to Chicago. Find affordable one-way fares based on user searches. Data last updated October 5, 2026.
This Southwest deal was found by Cheapflights users on 10/3. 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 1/83:45 pm -
1 stop10h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/3![Southwest logo]()
$212
This United Airlines deal was found by Cheapflights users on 10/2. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2912:46 pm -
1 stop13h 27m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/2![United Airlines logo]()
$212
This American Airlines deal was found by Cheapflights users on 10/2. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/171:55 pm -
1 stop10h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/2![American Airlines logo]()
$216
This Expedia deal was found by Cheapflights users on 10/3. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/810:32 am -
1 stop22h 43m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/3![Alaska Airlines logo]()
$217
This Delta deal was found by Cheapflights users on 10/2. 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.
Thu 10/299:53 pm -
2 stops15h 17m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/2![Delta logo]()
$218
This Delta deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/179:53 pm -
2 stops17h 37m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![Delta logo]()
$228
This Delta deal was found by Cheapflights users on 10/2. 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.
Sat 1/1610:26 pm -
1 stop11h 21m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/2![Delta logo]()
$245
This Alaska Airlines deal was found by Cheapflights users on 10/1. Clicking the “Pick Dates” 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 10/301:55 pm -
1 stop10h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/1![Alaska Airlines logo]()
$245
This Southwest deal was found by Cheapflights users on 10/3. 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 11/28:15 am -
1 stop16h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/3![Southwest logo]()
$253
This Alaska Airlines deal was found by Cheapflights users on 10/2. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 1/1911:34 pm -
1 stop18h 34m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/2![Alaska Airlines logo]()
$253
This Southwest deal was found by Cheapflights users on 10/4. 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.
Tue 11/311:15 pm -
2 stops14h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/4![Southwest logo]()
$259
This Delta deal was found by Cheapflights users on 10/4. 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 11/310:51 pm -
2 stops13h 56m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/4![Delta logo]()
$278
Find flight deals from Hawaii to Chicago
Keep the following information in mind while searching for Hawaii to Chicago flight deals. Data was last updated October 5, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $424 (Alaska Airlines) |
One-way from | $212 (Southwest) |
Popular in | June |
Cheapest in | February |
Average price | $888 |
Good round-trip deal | $557 or less |
Good one-way deal | $327 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Hawaii to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated October 5, 2026.
Use the filters below to find and compare flights from Hawaii to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
LihueChicago
LIH Lihue - MDW Chicago Midway
LIHMDW
Lihue
Fri 1/8
3:45 pm-5:50 am
1 stop10h 05m
Chicago Midway
Wed 12/31
12:00 am-8:00 pm
Nonstop0h 00m
$212
LihueChicago
LIH Lihue - ORD Chicago O'Hare Intl
LIHORD
Lihue
Thu 10/29
12:46 pm-7:13 am
1 stop13h 27m
Chicago O'Hare Intl
Wed 12/31
12:00 am-8:00 pm
Nonstop0h 00m
$212
LihueChicago
LIH Lihue - ORD Chicago O'Hare Intl
LIHORD
Lihue
Sat 10/17
9:53 pm-1:30 pm
1 stop10h 37m
Chicago O'Hare Intl
Wed 12/31
12:00 am-8:00 pm
Nonstop0h 00m
$212
LihueChicago
LIH Lihue - ORD Chicago O'Hare Intl
LIHORD
Lihue
Thu 3/25
1:10 pm-5:05 am
1 stop10h 55m
Chicago O'Hare Intl
Wed 12/31
12:00 am-8:00 pm
Nonstop0h 00m
$212
LihueChicago
LIH Lihue - ORD Chicago O'Hare Intl
LIHORD
Lihue
Fri 11/6
6:00 am-11:49 pm
2 stops13h 49m
Chicago O'Hare Intl
Wed 12/31
12:00 am-8:00 pm
Nonstop0h 00m
$218
LihueChicago
LIH Lihue - ORD Chicago O'Hare Intl
LIHORD
Lihue
Thu 10/29
9:53 pm-6:10 pm
2 stops15h 17m
Chicago O'Hare Intl
Wed 12/31
12:00 am-8:00 pm
Nonstop0h 00m
$218
LihueChicago
LIH Lihue - ORD Chicago O'Hare Intl
LIHORD
Lihue
Fri 1/29
10:45 pm-8:37 pm
2 stops17h 52m
Chicago O'Hare Intl
Wed 12/31
12:00 am-8:00 pm
Nonstop0h 00m
$218
LihueChicago
LIH Lihue - ORD Chicago O'Hare Intl
LIHORD
Lihue
Sat 1/16
10:24 am-1:15 pm
2 stops22h 51m
Chicago O'Hare Intl
Wed 12/31
12:00 am-8:00 pm
Nonstop0h 00m
$222
HonoluluChicago
HNL Honolulu - ORD Chicago O'Hare Intl
HNLORD
Honolulu
Tue 1/19
11:34 pm-10:08 pm
1 stop18h 34m
Chicago O'Hare Intl
Wed 12/31
12:00 am-8:00 pm
Nonstop0h 00m
$253
HonoluluChicago
HNL Honolulu - ORD Chicago O'Hare Intl
HNLORD
Honolulu
Tue 1/19
12:50 pm-1:15 pm
1 stop20h 25m
Chicago O'Hare Intl
Wed 12/31
12:00 am-8:00 pm
Nonstop0h 00m
$253
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Hawaii to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Hawaii with our price prediction graph.
LIH-ORD
HNL-ORD
HNL-MDW
LIH-MDW
KOA-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
USHI-CHI
LIH-ORD
HNL-ORD
HNL-MDW
LIH-MDW
What is the cheapest month to book a flight from Hawaii to Chicago?
Currently, January is the cheapest month in which you can book a flight from Hawaii to Chicago (average of $527). Flying from Hawaii to Chicago in June is currently the most expensive (average of $993). 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 HI to CHI?
Find hourly flight availability from Hawaii to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated October 5, 2026.
When flying from Hawaii to Chicago, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.
Weekly flight availability from Hawaii to Chicago
Explore weekly flight availability from Hawaii to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated October 5, 2026.
The most flights from USHI to CHI are scheduled on a Monday (2 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (2 on average).
How much does it cost to fly round-trip from Hawaii to Chicago?
Airfare is below average for this route at the moment.
Hawaii to Chicago flights typically cost between $760 and $1,105 in February.The cheapest round-trip price found within the last 5 days was $490 on Alaska Airlines (Feb 2-Feb 3).
How far ahead should I book a flight from Hawaii to Chicago?
To ensure you get the cheapest price possible for a flight from Hawaii to Chicago, you should look to book at least 79 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.
Related info for your journey
Find useful and relevant information for your journey from Hawaii to Chicago. 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?
Book flights to Chicago if you plan to visit one of these locationsBenton Harbor
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter
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
Chicago flight routes
Complete your trip
Flights by cabin class
Other flight options
Popular flights
Top destinations
Alternative routes for Hawaii to Chicago
See prices for flight routes from nearby airports that may be better suited for you.
Other flights to Chicago
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on October 5, 2026.
Complete your trip
Complete your trip to Chicago by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Hawaii to Chicago by cabin class
Find flights from Hawaii to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Hawaii and Chicago flights
Browse other Hawaii and Chicago flight options. Last updated on October 5, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Hawaii to Chicago flights
Consider these flights traveling from Hawaii to Chicago.
Top 5 airlines flying from Hawaii to Chicago
Discover the top 5 airlines that operate flights from Hawaii to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated October 5, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$217 | Average$513 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$330 | Average$712 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$416 | Average$709 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$444 | Average$804 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$494 | Average$764 | FlexibilityNo cancel fee | On-time63% |