$485+ Cheap flights from Chicago (CHI) to Osaka (OSA)
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 11/15. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — OSA
Oct 1 — Oct 81
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Osaka 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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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 Osaka
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Cheapest flights from Chicago to OsakaExplore the most affordable flight options available from Chicago to Osaka. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 1, 2026.
Explore the most affordable flight options available from Chicago to Osaka. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 1, 2026.
This Gotogate deal was found by Cheapflights users on 8/30. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/53:40 pm -
1 stop34h 45m
Mon 9/216:00 pm -
1 stop34h 43m
Deal found 8/30![Air Canada logo]()
$782
This Gotogate deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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.
Sat 8/293:40 pm -
1 stop34h 45m
Mon 9/146:00 pm -
1 stop34h 43m
Deal found 8/27![Air Canada logo]()
$786
This Trip.com deal was found by Cheapflights users on 8/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/308:49 am -
1 stop17h 36m
Tue 9/156:00 pm -
1 stop16h 06m
Deal found 8/29![Air Canada logo]()
$802
This Air Canada deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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.
Tue 9/153:40 pm -
1 stop34h 45m
Tue 9/296:00 pm -
1 stop34h 43m
Deal found 8/27![Air Canada logo]()
$819
This Air Canada deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” 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.
Sun 9/205:00 am -
2 stops21h 25m
Thu 10/86:00 pm -
2 stops29h 35m
Deal found 8/28![Air Canada logo]()
$826
This Booking.com deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/75:55 am -
2 stops20h 30m
Mon 9/146:00 pm -
2 stops19h 59m
Deal found 8/31![Air Canada logo]()
$827
This Gotogate deal was found by Cheapflights users on 8/30. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/139:50 am -
2 stops20h 00m
Wed 9/162:35 pm -
2 stops19h 37m
Deal found 8/30![Multiple Airlines logo]()
$980
This American Airlines deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/282:30 pm -
1 stop28h 15m
Wed 11/48:30 am -
1 stop16h 30m
Deal found 8/31![American Airlines logo]()
$1,031
This Bravofly deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Bravofly is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/311:50 am -
1 stop17h 05m
Thu 9/108:00 am -
1 stop14h 40m
Deal found 8/28![ANA logo]()
$1,049
This American Airlines deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 9/158:23 am -
2 stops20h 17m
Tue 9/291:25 pm -
2 stops20h 11m
Deal found 8/27![American Airlines logo]()
$1,059
This Ovago deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Ovago is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/710:15 am -
1 stop19h 35m
Mon 9/141:25 pm -
1 stop35h 20m
Deal found 8/31![Japan Airlines logo]()
$1,063
This Air Canada deal was found by Cheapflights users on 8/29. Clicking the “Pick Dates” 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.
Tue 9/158:50 am -
2 stops19h 20m
Tue 9/2912:50 pm -
2 stops20h 58m
Deal found 8/29![Air Canada logo]()
$1,068
Best flights from Chicago to OsakaDiscover carefully curated flight deals from Chicago to Osaka that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 1, 2026.
Discover carefully curated flight deals from Chicago to Osaka that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 1, 2026.
This Delta deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 9/159:59 am -
2 stops22h 41m
Tue 9/299:05 am -
2 stops27h 39m
Deal found 8/31![Delta logo]()
$1,083
This oojo deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/2712:30 am -
1 stop27h 30m
Wed 11/117:00 pm -
1 stop39h 35m
Deal found 8/28![EVA Air logo]()
$1,122
This Japan Airlines deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Japan Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1710:15 am -
1 stop19h 35m
Mon 9/2110:25 am -
1 stop14h 20m
Deal found 8/27![Japan Airlines logo]()
$1,165
This United Airlines deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” 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 9/236:00 am -
1 stop18h 50m
Wed 9/304:55 pm -
2 stops20h 37m
Deal found 8/26![United Airlines logo]()
$1,172
This Turkish Airlines deal was found by Cheapflights users on 8/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Turkish Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/288:15 pm -
1 stop31h 40m
Fri 2/1210:45 pm -
1 stop34h 35m
Deal found 8/29![Turkish Airlines logo]()
$1,194
This Cheapflightsfares deal was found by Cheapflights users on 8/30. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/2811:30 am -
1 stop17h 30m
Mon 11/98:20 pm -
1 stop26h 00m
Deal found 8/30![ANA logo]()
$1,256
This Philippine Airlines deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Philippine Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/3012:00 pm -
2 stops29h 55m
Sun 11/89:20 pm -
1 stop34h 35m
Deal found 8/28![Multiple Airlines logo]()
$1,260
This Cathay Pacific deal was found by Cheapflights users on 8/30. 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 Cathay Pacific is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/283:10 pm -
2 stops33h 45m
Mon 11/94:15 pm -
2 stops35h 40m
Deal found 8/30![Cathay Pacific logo]()
$1,272
This Korean Air deal was found by Cheapflights users on 8/30. 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 Korean Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/611:15 am -
1 stop31h 55m
Tue 11/176:40 pm -
1 stop28h 50m
Deal found 8/30![Korean Air logo]()
$1,333
This American Airlines deal was found by Cheapflights users on 8/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/286:55 am -
2 stops21h 45m
Mon 11/93:30 pm -
2 stops19h 50m
Deal found 8/29![American Airlines logo]()
$1,357
This FlightHub deal was found by Cheapflights users on 8/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/2712:30 am -
1 stop27h 30m
Mon 11/97:00 pm -
1 stop39h 35m
Deal found 8/29![EVA Air logo]()
$1,124
This United Airlines deal was found by Cheapflights users on 8/29. Clicking the “Pick Dates” 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.
Sat 9/269:40 pm -
1 stop27h 10m
Sat 10/39:20 am -
2 stops33h 25m
Deal found 8/29![United Airlines logo]()
$1,221
This Cathay Pacific deal was found by Cheapflights users on 8/30. 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 Cathay Pacific is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/283:10 pm -
2 stops33h 45m
Wed 11/114:15 pm -
2 stops35h 40m
Deal found 8/30![Cathay Pacific logo]()
$1,272
This Delta deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 10/286:04 am -
2 stops26h 36m
Tue 11/102:15 am -
2 stops25h 36m
Deal found 8/31![Delta logo]()
$1,296
This China Airlines deal was found by Cheapflights users on 8/30. 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 China Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/283:30 pm -
2 stops30h 05m
Mon 11/97:00 pm -
2 stops25h 55m
Deal found 8/30![Multiple Airlines logo]()
$1,303
This EVA Air deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure EVA Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/712:30 am -
1 stop27h 30m
Thu 9/107:00 pm -
1 stop39h 45m
Deal found 8/26![EVA Air logo]()
$1,217
This Cheapflightsfares deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/225:45 pm -
1 stop24h 20m
Sat 10/318:00 am -
1 stop14h 20m
Deal found 8/26![ANA logo]()
$1,354
This United Airlines deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/174:25 pm -
1 stop34h 45m
Tue 11/242:30 pm -
1 stop15h 40m
Deal found 8/27![United Airlines logo]()
$1,274
This China Airlines deal was found by Cheapflights users on 8/30. 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 China Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/284:45 pm -
3 stops28h 50m
Wed 11/117:00 pm -
2 stops25h 55m
Deal found 8/30![Multiple Airlines logo]()
$1,303
This iWofly deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure iWofly is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/1412:30 am -
1 stop27h 30m
Mon 10/197:00 pm -
1 stop39h 45m
Deal found 8/28![EVA Air logo]()
$1,266
This American Airlines deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” 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.
Thu 10/2210:15 am -
1 stop19h 35m
Sat 10/314:25 pm -
2 stops20h 35m
Deal found 8/26![American Airlines logo]()
$1,544
This United Airlines deal was found by Cheapflights users on 8/30. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/165:00 am -
2 stops22h 10m
Wed 11/252:30 pm -
1 stop15h 40m
Deal found 8/30![United Airlines logo]()
$1,279
This China Airlines deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 9/145:55 pm -
2 stops28h 05m
Sun 9/277:05 pm -
2 stops24h 50m
Deal found 8/31![Multiple Airlines logo]()
$1,333
This CheapTickets deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapTickets is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/1012:30 am -
1 stop19h 30m
Sun 10/187:00 pm -
1 stop39h 45m
Deal found 8/27![EVA Air logo]()
$1,267
This United Airlines deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 11/186:04 am -
2 stops21h 06m
Tue 11/242:30 pm -
1 stop31h 50m
Deal found 8/27![United Airlines logo]()
$1,279
This United Airlines deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 10/286:00 am -
2 stops20h 45m
Wed 11/116:35 pm -
2 stops19h 11m
Deal found 8/31![United Airlines logo]()
$1,286
This SmartFares deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/2112:30 am -
1 stop19h 30m
Sat 10/317:00 pm -
1 stop39h 35m
Deal found 8/26![EVA Air logo]()
$1,291
This Gotogate deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” 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.
Thu 10/1510:15 am -
1 stop19h 35m
Mon 10/192:00 pm -
2 stops19h 48m
Deal found 8/28![Multiple Airlines logo]()
$1,481
This United Airlines deal was found by Cheapflights users on 8/30. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/185:00 am -
2 stops19h 50m
Wed 10/286:35 pm -
2 stops19h 24m
Deal found 8/30![United Airlines logo]()
$1,286
This oojo deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/176:35 pm -
2 stops32h 25m
Tue 12/17:00 pm -
2 stops27h 00m
Deal found 8/28![EVA Air logo]()
$1,341
Last-minute flights from Chicago to OsakaDiscover last-minute flight deals from Chicago to Osaka. Data last updated September 1, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Osaka. Data last updated September 1, 2026 and is based on user searches.
This Bravofly deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Bravofly is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/311:50 am -
1 stop17h 05m
Thu 9/108:00 am -
1 stop14h 40m
Deal found 8/28![ANA logo]()
$1,049
This Gotogate deal was found by Cheapflights users on 8/30. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/53:40 pm -
1 stop34h 45m
Mon 9/216:00 pm -
1 stop34h 43m
Deal found 8/30![Air Canada logo]()
$782
This Booking.com deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/75:55 am -
2 stops20h 30m
Mon 9/146:00 pm -
2 stops19h 59m
Deal found 8/31![Air Canada logo]()
$827
This Ovago deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Ovago is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/710:15 am -
1 stop19h 35m
Mon 9/141:25 pm -
1 stop35h 20m
Deal found 8/31![Japan Airlines logo]()
$1,063
This Air Canada deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” 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 9/108:50 am -
1 stop17h 35m
Mon 9/216:00 pm -
2 stops27h 51m
Deal found 8/28![Air Canada logo]()
$833
This Gotogate deal was found by Cheapflights users on 8/30. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/139:50 am -
2 stops20h 00m
Wed 9/162:35 pm -
2 stops19h 37m
Deal found 8/30![Multiple Airlines logo]()
$980
This Air Canada deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 9/148:49 am -
1 stop17h 36m
Wed 9/166:00 pm -
1 stop29h 53m
Deal found 8/27![Air Canada logo]()
$829
This Air Canada deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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.
Tue 9/153:40 pm -
1 stop34h 45m
Tue 9/296:00 pm -
1 stop34h 43m
Deal found 8/27![Air Canada logo]()
$819
This American Airlines deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 9/158:23 am -
2 stops20h 17m
Tue 9/291:25 pm -
2 stops20h 11m
Deal found 8/27![American Airlines logo]()
$1,059
This Air Canada deal was found by Cheapflights users on 8/29. Clicking the “Pick Dates” 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.
Tue 9/158:50 am -
2 stops19h 20m
Tue 9/2912:50 pm -
2 stops20h 58m
Deal found 8/29![Air Canada logo]()
$1,068
This Delta deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 9/159:59 am -
2 stops22h 41m
Tue 9/2912:35 pm -
2 stops24h 09m
Deal found 8/27![Delta logo]()
$1,068
This Air Canada deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” 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.
Sun 9/205:00 am -
2 stops21h 25m
Thu 10/86:00 pm -
2 stops29h 35m
Deal found 8/28![Air Canada logo]()
$826
One-way flights from Chicago to OsakaSearch for one-way flight options from Chicago to Osaka. Find affordable one-way fares based on user searches. Data last updated September 1, 2026.
Search for one-way flight options from Chicago to Osaka. Find affordable one-way fares based on user searches. Data last updated September 1, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/151:06 pm -
2 stops53h 04m
Deal found 8/30![Multiple Airlines logo]()
$485
This Kiwi.com deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 10/301:06 pm -
2 stops53h 49m
Deal found 8/31![Multiple Airlines logo]()
$488
This Kiwi.com deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 10/301:06 pm -
2 stops52h 24m
Deal found 8/31![Multiple Airlines logo]()
$519
This Kiwi.com deal was found by Cheapflights users on 8/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/151:06 pm -
2 stops38h 54m
Deal found 8/30![Multiple Airlines logo]()
$529
This Kiwi.com deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” 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 11/91:06 pm -
2 stops53h 04m
Deal found 8/28![Multiple Airlines logo]()
$540
This Cheapflightsfares deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/1810:45 pm -
1 stop30h 20m
Deal found 8/27![Philippine Airlines logo]()
$605
This Trip.com deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/128:01 pm -
2 stops52h 09m
Deal found 8/28![Multiple Airlines logo]()
$617
This Kiwi.com deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” 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 11/96:42 pm -
3 stops47h 28m
Deal found 8/28![Multiple Airlines logo]()
$622
This Expedia deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 11/184:25 pm -
1 stop33h 45m
Deal found 8/27![ANA logo]()
$629
This Expedia deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 11/181:05 pm -
1 stop27h 55m
Deal found 8/27![ANA logo]()
$629
This oojo deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/137:00 am -
1 stop21h 45m
Deal found 8/28![Japan Airlines logo]()
$632
This United Airlines deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” 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.
Mon 10/126:07 am -
1 stop18h 43m
Deal found 8/28![United Airlines logo]()
$636
Find flight deals from Chicago to Osaka
Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Osaka (OSA). 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 September 1, 2026.
Most accurate provider | Ovago 3 stars |
|---|---|
Most trusted provider | Ovago 3 stars |
Round-trip from | $819 (Air Canada) |
One-way from | $485 (Kiwi.com) |
Popular in | December |
Cheapest in | May |
Average price | $1,114 |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to Osaka 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 September 1, 2026.
Use the filters below to find and compare flights from Chicago to Osaka that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoOsaka
MDW Chicago Midway - KIX Osaka Kansai Intl
MDWKIX
Chicago Midway
Tue 9/15
9:59 am-10:40 pm
2 stops22h 41m
Osaka Kansai Intl
Tue 9/29
9:05 am-10:44 pm
2 stops27h 39m
$1,083
ChicagoKobe
ORD Chicago O'Hare Intl - UKB Kobe
ORDUKB
Chicago O'Hare Intl
Tue 10/27
12:30 am-6:00 pm
1 stop27h 30m
Kobe
Wed 11/11
7:00 pm-7:35 pm
1 stop39h 35m
$1,122
ChicagoKobe
ORD Chicago O'Hare Intl - UKB Kobe
ORDUKB
Chicago O'Hare Intl
Tue 10/27
12:30 am-6:00 pm
1 stop27h 30m
Kobe
Mon 11/9
7:00 pm-7:35 pm
1 stop39h 35m
$1,124
Quickest round-trip
ChicagoOsaka
ORD Chicago O'Hare Intl - ITM Osaka Itami
ORDITM
Chicago O'Hare Intl
Thu 9/17
10:15 am-7:50 pm
1 stop19h 35m
Osaka Itami
Mon 9/21
10:25 am-10:45 am
1 stop14h 20m
$1,165
ChicagoOsaka
ORD Chicago O'Hare Intl - KIX Osaka Kansai Intl
ORDKIX
Chicago O'Hare Intl
Wed 9/23
6:00 am-2:50 pm
1 stop18h 50m
Osaka Kansai Intl
Wed 9/30
4:55 pm-11:32 pm
2 stops20h 37m
$1,172
ChicagoOsaka
ORD Chicago O'Hare Intl - KIX Osaka Kansai Intl
ORDKIX
Chicago O'Hare Intl
Thu 1/28
8:15 pm-6:55 pm
1 stop31h 40m
Osaka Kansai Intl
Fri 2/12
10:45 pm-6:20 pm
1 stop34h 35m
$1,194
ChicagoKobe
ORD Chicago O'Hare Intl - UKB Kobe
ORDUKB
Chicago O'Hare Intl
Mon 9/7
12:30 am-6:00 pm
1 stop27h 30m
Kobe
Thu 9/10
7:00 pm-8:45 pm
1 stop39h 45m
$1,217
ChicagoOsaka
ORD Chicago O'Hare Intl - KIX Osaka Kansai Intl
ORDKIX
Chicago O'Hare Intl
Sat 9/26
9:40 pm-2:50 pm
1 stop27h 10m
Osaka Kansai Intl
Sat 10/3
9:20 am-4:45 am
2 stops33h 25m
$1,221
ChicagoOsaka
ORD Chicago O'Hare Intl - ITM Osaka Itami
ORDITM
Chicago O'Hare Intl
Wed 10/28
11:30 am-7:00 pm
1 stop17h 30m
Osaka Itami
Mon 11/9
8:20 pm-7:20 am
1 stop26h 00m
$1,256
ChicagoOsaka
ORD Chicago O'Hare Intl - KIX Osaka Kansai Intl
ORDKIX
Chicago O'Hare Intl
Fri 10/30
12:00 pm-7:55 am
2 stops29h 55m
Osaka Kansai Intl
Sun 11/8
9:20 pm-4:55 pm
1 stop34h 35m
$1,260
Showing 1-10 of 60 resultsSorted by cheapest first
Compare providers for flights from Chicago to Osaka
Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Chicago to Osaka in September.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Chicago-Osaka flights, users find the pricing of Ovago to be most consistent on Cheapflights vs. Ovago Users can find the same prices on Chicago-Osaka flight deals on Cheapflights vs. Ovago >95% of the time. Price accuracy is based on data collected from Chicago-Osaka flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Chicago-Osaka flights, Cheapflights users trust Ovago the most. Ovago 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 Chicago-Osaka 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 Chicago to Osaka
Have a flexible travel schedule? Discover the best time to fly to Osaka from Chicago with our price prediction graph.
CHI-OSA
MDW-KIX
ORD-UKB
ORD-ITM
ORD-KIX
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 Osaka
CHI-OSA
MDW-KIX
ORD-UKB
ORD-ITM
ORD-KIX
What is the cheapest month to book a flight from Chicago to Osaka?
Currently, October is the cheapest month in which you can book a flight from Chicago to Osaka (average of $1,097). Flying from Chicago to Osaka in December is currently the most expensive (average of $1,988). 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.
How much does it cost to fly round-trip from Chicago to Osaka?
Airfare is below average for this route at the moment.
Chicago to Osaka flights typically cost between $1,059 and $1,362 in September.The cheapest round-trip price found within the last 5 days was $819 on Air Canada (Sep 15-Sep 29).
What’s the top layover airport for flights from Chicago to Osaka?
Share of 1-stop round-trip flights from Chicago to Osaka chosen by Cheapflights users in the past 12 months, using the same layover each way.
Tokyo (HND) – chosen by Cheapflights users on 75% of 1-stop itineraries from Chicago to Osaka on Cheapflights.
What’s the cheapest layover airport for flights from Chicago to Osaka?
Average round-trip fare for 1-stop flights from Chicago to Osaka, chosen by Cheapflights users in the past 12 months, with the same layover each way.
Tokyo (HND) is the most affordable 1-stop option, with an average round-trip price of $1,196.
What’s the fastest layover option from Chicago to Osaka?
Shortest average travel time for 1-stop one-way flights from Chicago to Osaka, based on itineraries clicked by Cheapflights users over the past 12 months, grouped by layover airport.
Flights via Taipei City (TPE) have the shortest average one-way travel time for 1-stop routes: 19h 30m.
Which airport typically offers the quickest layover for flights from Chicago to Osaka?
Average layover duration for 1-stop one-way flights from Chicago to Osaka, chosen by Cheapflights users in the last 12 months, grouped by stopover airport.
Flights via Taipei City (TPE) offer the fastest connection on this route, with an average layover time of 3h 23m.
How often are flights from Chicago to Osaka delayed?
About 34% of weekly flights between Chicago and Osaka have experienced delays in the past year, with the average delay time being 162 minutes.
What is the most punctual flight time for Chicago to Osaka flights?
Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving at night tend to experience delays more often.
What day of the week experiences the fewest flight delays on this route?
Monday tends to have the lowest number of delays on this route, whereas Wednesday has historically faced a higher average of delays compared to other days of the week.
Which airline has the best punctuality record on Chicago to Osaka flights?
Over the last year, China Airlines have had the lowest number of delays on this route, with just 31% of flights being delayed.
Reviews of airlines servicing Osaka
Get insights into the airlines that provide service to Osaka. 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 Osaka. Reviews last updated September 1, 2026.
Read reviews from past customers who have flown EVA Air,Japan Airlines, andANA from Chicago to Osaka. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Food
8.1
Boarding
8.5
Entertainment
8.0
Overall
8.5
Comfort
8.3
Crew
8.7
Reviews
1 / 20
10.0
ExcellentDaisy,May 2026
SFO - TPE
Food
8.1
Boarding
8.5
Entertainment
8.0
Overall
8.5
Comfort
8.3
Crew
8.7
Reviews
1 / 20
10.0
ExcellentDaisy,May 2026
SFO - TPE
Food
8.1
Boarding
8.5
Entertainment
8.0
Overall
8.5
Comfort
8.3
Crew
8.7
Reviews
1 / 20
10.0
ExcellentDaisy,May 2026
SFO - TPE
Food
8.1
Boarding
8.5
Entertainment
8.0
Overall
8.5
Comfort
8.3
Crew
8.7
Reviews
1 / 20
10.0
ExcellentDaisy,May 2026
SFO - TPE
Food
8.1
Boarding
8.5
Entertainment
8.0
Overall
8.5
Comfort
8.3
Crew
8.7
Reviews
1 / 20
10.0
ExcellentDaisy,May 2026
SFO - TPE
Food
8.1
Boarding
8.5
Entertainment
8.0
Overall
8.5
Comfort
8.3
Crew
8.7
Reviews
1 / 20
10.0
ExcellentDaisy,May 2026
SFO - TPE
Related info for your journey
Find useful and relevant information for your journey from Chicago to Osaka. 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 Osaka?
Book flights to Osaka if you plan to visit one of these locationsNara
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Other flights to Osaka
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Browse other Chicago and Osaka flight options. Last updated on September 1, 2026.
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Top 4 airlines flying from Chicago to Osaka
Discover the top 4 airlines that operate flights from Chicago to Osaka. 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 September 1, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$1,008 | Average$1,107 | FlexibilityNo cancel fee | On-time74% | |
| Cheapest$1,039 | Average$1,511 | FlexibilityNo cancel fee | On-time79% | |
| Cheapest$1,145 | Average$1,880 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$1,162 | Average$1,926 | FlexibilityNo cancel fee | On-time80% |