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$475+ 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 10/15. Fares are subject to change and may not be available on all flights or dates of travel.
OSA — CHI
Jun 11 — Jun 181
Thu 6/11
Thu 6/18
1 adult, Economy
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Cheap flight deals from Osaka to Chicago

Cheapest flights from Osaka to Chicago
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 May 12, 2026.

This China Airlines deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure China Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/222:00 pm
KIX
-
ORD
2 stops30h 22m
Multiple Airlines
Tue 9/297:00 pm
ORD
-
KIX
2 stops27h 00m
Multiple Airlines
Deal found 5/11$1,217
This Kiwi.com deal was found by Cheapflights users on 5/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/167:45 am
KIX
-
ORD
2 stops27h 49m
Multiple Airlines
Thu 9/2412:30 am
ORD
-
KIX
1 stop19h 40m
Multiple Airlines
Deal found 5/10$1,259
This Kiwi.com deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/187:45 am
KIX
-
ORD
2 stops27h 49m
Multiple Airlines
Tue 9/224:15 pm
ORD
-
KIX
1 stop24h 25m
Multiple Airlines
Deal found 5/11$1,292
This oojo deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/203:15 pm
KIX
-
ORD
1 stop40h 40m
Philippine Airlines
Wed 1/610:45 pm
ORD
-
KIX
1 stop29h 50m
Philippine Airlines
Deal found 5/11$1,314
This China Airlines deal was found by Cheapflights users on 5/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure China Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/227:05 pm
KIX
-
ORD
2 stops25h 17m
Multiple Airlines
Sat 8/298:42 pm
ORD
-
KIX
2 stops25h 18m
Multiple Airlines
Deal found 5/8$1,414
This Gotogate deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/225:35 pm
KIX
-
ORD
1 stop34h 45m
Cathay Pacific
Mon 6/294:00 pm
ORD
-
KIX
1 stop24h 40m
Cathay Pacific
Deal found 5/11$1,427
This oojo deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” 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.
Mon 6/159:05 am
KIX
-
ORD
1 stop43h 15m
Cathay Pacific
Fri 6/194:00 pm
ORD
-
KIX
1 stop24h 40m
Cathay Pacific
Deal found 5/12$1,431
This oojo deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/255:35 pm
KIX
-
ORD
1 stop34h 45m
Cathay Pacific
Thu 7/24:00 pm
ORD
-
KIX
1 stop36h 05m
Cathay Pacific
Deal found 5/11$1,434
This Gotogate deal was found by Cheapflights users on 5/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/249:05 am
KIX
-
ORD
1 stop43h 15m
Cathay Pacific
Wed 7/14:00 pm
ORD
-
KIX
1 stop24h 40m
Cathay Pacific
Deal found 5/10$1,437
This Gotogate deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” 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.
Wed 6/34:15 pm
KIX
-
ORD
2 stops35h 40m
Cathay Pacific
Thu 6/184:00 pm
ORD
-
KIX
1 stop39h 15m
Cathay Pacific
Deal found 5/12$1,443
This oojo deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” 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.
Thu 7/27:25 pm
KIX
-
ORD
1 stop32h 55m
Cathay Pacific
Wed 7/154:00 pm
ORD
-
KIX
2 stops32h 50m
Cathay Pacific
Deal found 5/12$1,447
This oojo deal was found by Cheapflights users on 5/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/14:15 pm
KIX
-
ORD
2 stops35h 40m
Cathay Pacific
Tue 8/44:00 pm
ORD
-
KIX
1 stop24h 40m
Cathay Pacific
Deal found 5/9$1,449

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 May 12, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$1,217
(China Airlines)

One-way from

$475
(Kiwi.com)
Provider with most accurate pricing for Osaka (OSA)-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Osaka (OSA)-Chicago (CHI) flights.
Search Deals
From Osaka (OSA) to Chicago (CHI)
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One-way flight from Osaka (OSA) to Chicago (CHI)
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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 2,558,603 searches. Data last updated May 12, 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

Price

Cheapest round-trip

OsakaChicago

KIX - ORD

KIXORD

Osaka Kansai Intl

Tue 9/22

2:00 pm-6:22 am

2 stops30h 22m

Chicago O'Hare Intl

Tue 9/29

7:00 pm-12:00 pm

2 stops27h 00m

$1,217

OsakaChicago

KIX - ORD

KIXORD

Osaka Kansai Intl

Sat 8/22

7:05 pm-6:22 am

2 stops25h 17m

Chicago O'Hare Intl

Sat 8/29

8:42 pm-12:00 pm

2 stops25h 18m

$1,414

OsakaChicago

KIX - ORD

KIXORD

Osaka Kansai Intl

Mon 6/15

9:05 am-2:20 pm

1 stop43h 15m

Chicago O'Hare Intl

Fri 6/19

4:00 pm-6:40 am

1 stop24h 40m

$1,431

OsakaChicago

KIX - ORD

KIXORD

Osaka Kansai Intl

Fri 9/18

11:10 am-8:45 pm

1 stop23h 35m

Chicago O'Hare Intl

Tue 9/22

4:15 pm-6:40 am

1 stop24h 25m

$1,516

OsakaChicago

KIX - ORD

KIXORD

Osaka Kansai Intl

Wed 6/3

4:15 pm-1:55 pm

2 stops35h 40m

Chicago O'Hare Intl

Thu 6/18

4:00 pm-2:50 pm

2 stops32h 50m

$1,553

OsakaChicago

KIX - ORD

KIXORD

Osaka Kansai Intl

Thu 6/11

5:35 pm-1:55 pm

1 stop34h 20m

Chicago O'Hare Intl

Tue 6/23

4:00 pm-6:40 am

1 stop24h 40m

$1,619

OsakaChicago

KIX - ORD

KIXORD

Osaka Kansai Intl

Wed 5/27

2:00 pm-11:55 pm

2 stops23h 55m

Chicago O'Hare Intl

Thu 5/28

7:49 pm-12:50 pm

2 stops27h 01m

$1,621

OsakaChicago

KIX - MDW

KIXMDW

Osaka Kansai Intl

Wed 6/10

7:05 pm-5:55 am

2 stops24h 50m

Chicago Midway

Wed 6/17

3:50 pm-12:50 pm

2 stops31h 00m

$1,627

OsakaChicago

KIX - MDW

KIXMDW

Osaka Kansai Intl

Fri 7/31

2:00 pm-12:35 am

2 stops24h 35m

Chicago Midway

Sun 8/9

8:35 pm-12:00 pm

2 stops25h 25m

$1,664

OsakaChicago

KIX - MDW

KIXMDW

Osaka Kansai Intl

Wed 6/24

7:05 pm-5:55 am

2 stops24h 50m

Chicago Midway

Wed 7/1

5:35 pm-12:50 pm

2 stops29h 15m

$1,667

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/10

Showing 1-10 of 50 resultsSorted by cheapest first
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  • 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.
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
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.

  • How long is the flight from Osaka to Chicago?

    Departing from Osaka to Chicago will take you 21h 05m. There are 6461 mi between Osaka and Chicago. This flight may include one or multiple stops.

  • What are the most popular routes from Osaka to Chicago?

    While some choose either Osaka Kansai Intl - Chicago Midway or Osaka Itami - Chicago O'Hare Intl, Osaka Kansai Intl - Chicago O'Hare Intl is the most popular route from Osaka to Chicago.

  • Can I find deals for flights from Osaka to Chicago that include hotel bookings?

    Yes. In addition to deals on Osaka to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Osaka to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Osaka to Chicago.

  • Can I find deals for business class flights from Osaka to Chicago?

    Yes. Cheapflights offers flight deals from Osaka to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Benton Harbor
Lansing
Merrillville
Hammond
Porter

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