$452+ Cheap flights from Osaka (OSA) to Chicago (CHI)
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 10/1. Fares are subject to change and may not be available on all flights or dates of travel.
OSA — CHI
Sep 20 — Sep 271
Round-trip
1 adult, Economy
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Find cheap flights from Osaka to Chicago with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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Cheapest flights from Osaka to ChicagoExplore the most affordable flight options available from Osaka to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 21, 2026.
Explore the most affordable flight options available from Osaka to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 21, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/57:35 am -
2 stops28h 04m
Mon 10/1911:50 am -
1 stop31h 25m
Deal found 8/18![Multiple Airlines logo]()
$1,021
This Kiwi.com deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” 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.
Wed 10/77:35 am -
2 stops20h 42m
Wed 10/215:45 pm -
1 stop29h 45m
Deal found 8/20![Multiple Airlines logo]()
$1,056
This Kiwi.com deal was found by Cheapflights users on 8/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/18:05 pm -
2 stops40h 29m
Sun 11/84:25 pm -
1 stop25h 20m
Deal found 8/18![Multiple Airlines logo]()
$1,121
This Kiwi.com deal was found by Cheapflights users on 8/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/18:05 pm -
2 stops40h 29m
Fri 11/610:30 am -
1 stop17h 10m
Deal found 8/18![Multiple Airlines logo]()
$1,136
This Kiwi.com deal was found by Cheapflights users on 8/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/167:45 am -
2 stops20h 32m
Wed 9/2311:50 am -
1 stop17h 25m
Deal found 8/18![Multiple Airlines logo]()
$1,137
This Kiwi.com deal was found by Cheapflights users on 8/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/147:35 am -
2 stops28h 04m
Thu 9/1711:50 am -
1 stop19h 00m
Deal found 8/18![Multiple Airlines logo]()
$1,149
This Kiwi.com deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/89:00 pm -
2 stops31h 17m
Thu 9/1711:50 am -
1 stop19h 00m
Deal found 8/19![Multiple Airlines logo]()
$1,150
This Kiwi.com deal was found by Cheapflights users on 8/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/119:00 pm -
2 stops31h 17m
Wed 9/165:45 pm -
1 stop24h 55m
Deal found 8/17![Multiple Airlines logo]()
$1,160
This Kiwi.com deal was found by Cheapflights users on 8/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/119:00 pm -
2 stops31h 17m
Thu 9/1711:50 am -
1 stop19h 00m
Deal found 8/17![Multiple Airlines logo]()
$1,169
This Gotogate deal was found by Cheapflights users on 8/16. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/146:00 pm -
1 stop34h 43m
Thu 9/173:40 pm -
1 stop34h 45m
Deal found 8/16![Air Canada logo]()
$1,173
This Kiwi.com deal was found by Cheapflights users on 8/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/18:20 pm -
2 stops40h 14m
Sun 11/810:30 am -
1 stop17h 25m
Deal found 8/18![Multiple Airlines logo]()
$1,184
This Kiwi.com deal was found by Cheapflights users on 8/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/18:20 pm -
2 stops40h 14m
Fri 11/610:30 am -
1 stop17h 25m
Deal found 8/18![Multiple Airlines logo]()
$1,193
Best flights from Osaka to ChicagoDiscover carefully curated flight deals from Osaka to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 21, 2026.
Discover carefully curated flight deals from Osaka to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 21, 2026.
This Air Canada deal was found by Cheapflights users on 8/16. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/226:00 pm -
1 stop16h 06m
Sun 10/253:30 pm -
1 stop36h 10m
Deal found 8/16![Air Canada logo]()
$1,184
This Cathay Pacific deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cathay Pacific is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/47:25 pm -
1 stop32h 30m
Sun 10/114:15 pm -
1 stop24h 25m
Deal found 8/19![Cathay Pacific logo]()
$1,308
This Expedia deal was found by Cheapflights users on 8/16. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/142:00 pm -
2 stops20h 12m
Thu 9/179:55 am -
2 stops19h 00m
Deal found 8/16![Multiple Airlines logo]()
$1,426
This Alaska Airlines deal was found by Cheapflights users on 8/17. 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.
Sun 11/17:30 pm -
2 stops37h 07m
Sun 11/87:00 am -
2 stops41h 55m
Deal found 8/17![Alaska Airlines logo]()
$1,893
This Qatar Airways deal was found by Cheapflights users on 8/17. 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 Qatar Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/198:05 pm -
2 stops33h 00m
Thu 10/17:20 pm -
2 stops34h 30m
Deal found 8/17![Qatar Airways logo]()
$2,077
This Cathay Pacific deal was found by Cheapflights users on 8/17. 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 Cathay Pacific is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/265:35 pm -
1 stop34h 20m
Mon 10/54:15 pm -
1 stop30h 40m
Deal found 8/17![Cathay Pacific logo]()
$1,310
This Cathay Pacific deal was found by Cheapflights users on 8/17. 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 Cathay Pacific is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/19:25 am -
1 stop42h 30m
Sun 11/82:35 pm -
1 stop24h 45m
Deal found 8/17![Cathay Pacific logo]()
$1,310
This Air Canada deal was found by Cheapflights users on 8/17. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/2112:50 pm -
2 stops20h 58m
Mon 9/287:09 am -
2 stops21h 01m
Deal found 8/17![Air Canada logo]()
$1,516
This Cathay Pacific deal was found by Cheapflights users on 8/17. 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 Cathay Pacific is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/229:45 am -
1 stop42h 10m
Wed 9/304:15 pm -
1 stop30h 40m
Deal found 8/17![Cathay Pacific logo]()
$1,310
This China Airlines deal was found by Cheapflights users on 8/18. 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 China Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/17:00 pm -
2 stops25h 55m
Sat 11/76:25 pm -
2 stops27h 55m
Deal found 8/18![Multiple Airlines logo]()
$1,643
This Cathay Pacific deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cathay Pacific is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/219:45 am -
1 stop42h 10m
Mon 9/284:15 pm -
1 stop35h 50m
Deal found 8/19![Cathay Pacific logo]()
$1,311
This China Airlines deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure China Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/87:05 pm -
2 stops24h 00m
Thu 9/175:55 pm -
2 stops28h 55m
Deal found 8/19![Multiple Airlines logo]()
$1,649
This Cathay Pacific deal was found by Cheapflights users on 8/18. 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 Cathay Pacific is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/165:35 pm -
1 stop34h 20m
Wed 9/234:15 pm -
1 stop32h 55m
Deal found 8/18![Cathay Pacific logo]()
$1,311
This Alaska Airlines deal was found by Cheapflights users on 8/18. 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.
Tue 2/22:40 pm -
2 stops18h 19m
Thu 2/257:55 pm -
3 stops33h 00m
Deal found 8/18![Alaska Airlines logo]()
$1,920
This China Airlines deal was found by Cheapflights users on 8/16. 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 China Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/227:05 pm -
2 stops24h 45m
Sun 10/255:40 pm -
2 stops27h 55m
Deal found 8/16![Multiple Airlines logo]()
$1,674
This Cathay Pacific deal was found by Cheapflights users on 8/16. 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 Cathay Pacific is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/164:15 pm -
2 stops35h 40m
Tue 2/232:35 pm -
1 stop24h 45m
Deal found 8/16![Cathay Pacific logo]()
$1,326
This China Airlines deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure China Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/47:05 pm -
2 stops24h 45m
Sun 10/116:10 pm -
2 stops27h 50m
Deal found 8/19![Multiple Airlines logo]()
$1,731
This Air Canada deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2212:55 pm -
2 stops20h 53m
Sun 10/258:45 am -
2 stops20h 25m
Deal found 8/20![Air Canada logo]()
$2,117
This China Airlines deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure China Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/217:00 pm -
2 stops25h 55m
Sat 1/96:00 pm -
2 stops26h 35m
Deal found 8/19![Multiple Airlines logo]()
$1,741
This China Airlines deal was found by Cheapflights users on 8/18. 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 China Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/57:05 pm -
2 stops24h 45m
Mon 10/193:55 pm -
2 stops30h 05m
Deal found 8/18![Multiple Airlines logo]()
$1,762
This Qatar Airways deal was found by Cheapflights users on 8/18. 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 Qatar Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/16:35 pm -
2 stops34h 55m
Sun 11/86:50 pm -
2 stops34h 00m
Deal found 8/18![Multiple Airlines logo]()
$1,819
This Qatar Airways deal was found by Cheapflights users on 8/17. 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 Qatar Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/227:40 pm -
2 stops33h 25m
Sun 10/257:50 pm -
2 stops34h 00m
Deal found 8/17![Multiple Airlines logo]()
$1,848
This China Airlines deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure China Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/157:05 pm -
2 stops24h 45m
Mon 10/193:55 pm -
2 stops30h 55m
Deal found 8/20![Multiple Airlines logo]()
$1,860
This Flightnetwork deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/47:05 am -
2 stops26h 43m
Sat 10/1012:30 am -
2 stops29h 20m
Deal found 8/19![Multiple Airlines logo]()
$1,916
This China Airlines deal was found by Cheapflights users on 8/17. 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 China Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/267:05 pm -
2 stops24h 50m
Mon 10/53:55 pm -
2 stops30h 05m
Deal found 8/17![Multiple Airlines logo]()
$1,928
This China Airlines deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure China Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/197:05 pm -
2 stops24h 50m
Thu 10/13:55 pm -
2 stops30h 05m
Deal found 8/21![Multiple Airlines logo]()
$2,044
This Gotogate deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/142:35 pm -
2 stops19h 13m
Sat 12/510:25 am -
1 stop18h 30m
Deal found 8/21![Multiple Airlines logo]()
$2,093
Last-minute flights from Osaka to ChicagoDiscover last-minute flight deals from Osaka to Chicago. Data last updated August 21, 2026 and is based on user searches.
Discover last-minute flight deals from Osaka to Chicago. Data last updated August 21, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/89:00 pm -
2 stops31h 17m
Thu 9/1711:50 am -
1 stop19h 00m
Deal found 8/19![Multiple Airlines logo]()
$1,150
This Kiwi.com deal was found by Cheapflights users on 8/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/82:00 pm -
2 stops38h 17m
Thu 9/1711:50 am -
1 stop17h 05m
Deal found 8/18![Multiple Airlines logo]()
$1,216
This Kiwi.com deal was found by Cheapflights users on 8/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/119:00 pm -
2 stops31h 17m
Wed 9/165:45 pm -
1 stop24h 55m
Deal found 8/17![Multiple Airlines logo]()
$1,160
This Kiwi.com deal was found by Cheapflights users on 8/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/119:00 pm -
2 stops31h 17m
Thu 9/1711:50 am -
1 stop19h 00m
Deal found 8/17![Multiple Airlines logo]()
$1,169
This Air Canada deal was found by Cheapflights users on 8/17. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/116:00 pm -
2 stops27h 51m
Wed 9/165:55 am -
2 stops20h 30m
Deal found 8/17![Air Canada logo]()
$1,200
This Kiwi.com deal was found by Cheapflights users on 8/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/112:35 pm -
2 stops37h 42m
Thu 9/1711:50 am -
1 stop17h 05m
Deal found 8/17![Multiple Airlines logo]()
$1,214
This Kiwi.com deal was found by Cheapflights users on 8/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/147:35 am -
2 stops28h 04m
Thu 9/1711:50 am -
1 stop19h 00m
Deal found 8/18![Multiple Airlines logo]()
$1,149
This Gotogate deal was found by Cheapflights users on 8/16. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/146:00 pm -
1 stop34h 43m
Thu 9/173:40 pm -
1 stop34h 45m
Deal found 8/16![Air Canada logo]()
$1,173
This Kiwi.com deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” 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 9/147:45 am -
2 stops27h 54m
Sat 12/510:30 am -
1 stop31h 15m
Deal found 8/21![Multiple Airlines logo]()
$1,217
This Expedia deal was found by Cheapflights users on 8/16. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/142:00 pm -
2 stops20h 12m
Thu 9/179:55 am -
2 stops19h 00m
Deal found 8/16![Multiple Airlines logo]()
$1,426
This Kiwi.com deal was found by Cheapflights users on 8/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/167:45 am -
2 stops20h 32m
Wed 9/2311:50 am -
1 stop17h 25m
Deal found 8/18![Multiple Airlines logo]()
$1,137
This Air Canada deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/2112:50 pm -
2 stops20h 58m
Mon 9/287:09 am -
2 stops21h 01m
Deal found 8/21![Air Canada logo]()
$1,465
One-way flights from Osaka to ChicagoSearch for one-way flight options from Osaka to Chicago. Find affordable one-way fares based on user searches. Data last updated August 21, 2026.
Search for one-way flight options from Osaka to Chicago. Find affordable one-way fares based on user searches. Data last updated August 21, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/19:00 pm -
2 stops38h 39m
Deal found 8/17![Multiple Airlines logo]()
$452
This Kiwi.com deal was found by Cheapflights users on 8/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/197:35 am -
2 stops28h 59m
Deal found 8/16![Multiple Airlines logo]()
$492
This Kiwi.com deal was found by Cheapflights users on 8/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/15:45 pm -
2 stops41h 54m
Deal found 8/17![Multiple Airlines logo]()
$497
This Kiwi.com deal was found by Cheapflights users on 8/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/88:05 pm -
2 stops40h 29m
Deal found 8/17![Multiple Airlines logo]()
$513
This Kiwi.com deal was found by Cheapflights users on 8/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/77:35 am -
2 stops30h 31m
Deal found 8/16![Multiple Airlines logo]()
$526
This Kiwi.com deal was found by Cheapflights users on 8/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/2311:45 am -
3 stops50h 38m
Deal found 8/18![Multiple Airlines logo]()
$541
This Kiwi.com deal was found by Cheapflights users on 8/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/119:00 pm -
2 stops31h 17m
Deal found 8/17![Multiple Airlines logo]()
$549
This Kiwi.com deal was found by Cheapflights users on 8/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/37:35 am -
3 stops27h 41m
Deal found 8/16![Multiple Airlines logo]()
$550
This Kiwi.com deal was found by Cheapflights users on 8/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/109:00 pm -
2 stops38h 39m
Deal found 8/17![Multiple Airlines logo]()
$558
This Kiwi.com deal was found by Cheapflights users on 8/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/21:25 pm -
3 stops48h 41m
Deal found 8/16![Multiple Airlines logo]()
$574
This Kiwi.com deal was found by Cheapflights users on 8/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/82:05 pm -
2 stops46h 29m
Deal found 8/17![Multiple Airlines logo]()
$575
This Kiwi.com deal was found by Cheapflights users on 8/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/112:35 pm -
2 stops37h 42m
Deal found 8/17![Multiple Airlines logo]()
$592
Find flight deals from Osaka to Chicago
Discover tips and strategies to find the most affordable flight options for your journey from Osaka (OSA) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated August 21, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $1,021 (Kiwi.com) |
One-way from | $452 (Kiwi.com) |
Cheapflights Fare Finder
Customize your flight search to find flights from Osaka 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 August 21, 2026.
Use the filters below to find and compare flights from Osaka to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
OsakaChicago
KIX Osaka Kansai Intl - ORD Chicago O'Hare Intl
KIXORD
Osaka Kansai Intl
Thu 10/22
6:00 pm-8:06 pm
1 stop16h 06m
Chicago O'Hare Intl
Sun 10/25
3:30 pm-5:40 pm
1 stop36h 10m
$1,184
OsakaChicago
KIX Osaka Kansai Intl - ORD Chicago O'Hare Intl
KIXORD
Osaka Kansai Intl
Sun 10/4
7:25 pm-1:55 pm
1 stop32h 30m
Chicago O'Hare Intl
Sun 10/11
4:15 pm-6:40 am
1 stop24h 25m
$1,308
OsakaChicago
KIX Osaka Kansai Intl - ORD Chicago O'Hare Intl
KIXORD
Osaka Kansai Intl
Sat 9/26
5:35 pm-1:55 pm
1 stop34h 20m
Chicago O'Hare Intl
Mon 10/5
4:15 pm-12:55 pm
1 stop30h 40m
$1,310
OsakaChicago
KIX Osaka Kansai Intl - ORD Chicago O'Hare Intl
KIXORD
Osaka Kansai Intl
Sun 11/1
9:25 am-1:55 pm
1 stop42h 30m
Chicago O'Hare Intl
Sun 11/8
2:35 pm-6:20 am
1 stop24h 45m
$1,310
OsakaChicago
KIX Osaka Kansai Intl - ORD Chicago O'Hare Intl
KIXORD
Osaka Kansai Intl
Tue 9/22
9:45 am-1:55 pm
1 stop42h 10m
Chicago O'Hare Intl
Wed 9/30
4:15 pm-12:55 pm
1 stop30h 40m
$1,310
OsakaChicago
KIX Osaka Kansai Intl - ORD Chicago O'Hare Intl
KIXORD
Osaka Kansai Intl
Mon 9/21
9:45 am-1:55 pm
1 stop42h 10m
Chicago O'Hare Intl
Mon 9/28
4:15 pm-6:05 pm
1 stop35h 50m
$1,311
OsakaChicago
KIX Osaka Kansai Intl - ORD Chicago O'Hare Intl
KIXORD
Osaka Kansai Intl
Wed 9/16
5:35 pm-1:55 pm
1 stop34h 20m
Chicago O'Hare Intl
Wed 9/23
4:15 pm-3:10 pm
1 stop32h 55m
$1,311
OsakaChicago
KIX Osaka Kansai Intl - ORD Chicago O'Hare Intl
KIXORD
Osaka Kansai Intl
Tue 2/16
4:15 pm-12:55 pm
2 stops35h 40m
Chicago O'Hare Intl
Tue 2/23
2:35 pm-6:20 am
1 stop24h 45m
$1,326
OsakaChicago
ITM Osaka Itami - ORD Chicago O'Hare Intl
ITMORD
Osaka Itami
Mon 9/14
2:00 pm-8:12 pm
2 stops20h 12m
Chicago O'Hare Intl
Thu 9/17
9:55 am-6:55 pm
2 stops19h 00m
$1,426
OsakaChicago
ITM Osaka Itami - ORD Chicago O'Hare Intl
ITMORD
Osaka Itami
Mon 9/21
12:50 pm-7:48 pm
2 stops20h 58m
Chicago O'Hare Intl
Mon 9/28
7:09 am-6:10 pm
2 stops21h 01m
$1,516
Showing 1-10 of 57 resultsSorted by cheapest first
- Most accurate provider: When it comes to deals on Osaka-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Osaka-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Osaka-Chicago flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Osaka-Chicago flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Osaka-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
Best time to book a flight from Osaka to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Osaka with our price prediction graph.
OSA-CHI
KIX-ORD
ITM-ORD
KIX-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 Osaka to Chicago
OSA-CHI
KIX-ORD
ITM-ORD
KIX-MDW
No data available for this route at this time. Please check back soon.
Related info for your journey
Find useful and relevant information for your journey from Osaka 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
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Saint Joseph
Porter
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