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$504+ 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 10/10. Fares are subject to change and may not be available on all flights or dates of travel.
OSA — CHI
Jul 29 — Aug 51
Wed 7/29
Wed 8/5
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 June 29, 2026.

This Kiwi.com deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” 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 9/19:00 pm
KIX
-
ORD
2 stops32h 59m
Multiple Airlines
Tue 9/811:50 am
ORD
-
KIX
1 stop19h 00m
Multiple Airlines
Deal found 6/24$1,195
This Kiwi.com deal was found by Cheapflights users on 6/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/17:35 am
KIX
-
ORD
2 stops36h 42m
Multiple Airlines
Wed 9/911:50 am
ORD
-
KIX
1 stop20h 10m
Multiple Airlines
Deal found 6/27$1,200
This Kiwi.com deal was found by Cheapflights users on 6/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/17:35 am
KIX
-
ORD
2 stops36h 42m
Multiple Airlines
Thu 9/1011:50 am
ORD
-
KIX
1 stop19h 00m
Multiple Airlines
Deal found 6/27$1,204
This Kiwi.com deal was found by Cheapflights users on 6/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/97:45 am
KIX
-
ORD
2 stops27h 49m
Multiple Airlines
Thu 10/1511:50 am
ORD
-
KIX
1 stop19h 00m
Multiple Airlines
Deal found 6/27$1,229
This Kiwi.com deal was found by Cheapflights users on 6/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/27:45 am
KIX
-
ORD
2 stops22h 14m
Multiple Airlines
Mon 9/1411:50 am
ORD
-
KIX
1 stop19h 00m
Multiple Airlines
Deal found 6/26$1,252
This Kiwi.com deal was found by Cheapflights users on 6/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/257:35 am
KIX
-
ORD
2 stops27h 59m
Multiple Airlines
Tue 9/2911:50 am
ORD
-
KIX
1 stop17h 25m
Multiple Airlines
Deal found 6/27$1,262
This Kiwi.com deal was found by Cheapflights users on 6/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/27:35 am
KIX
-
ORD
2 stops22h 24m
Multiple Airlines
Wed 9/911:50 am
ORD
-
KIX
1 stop31h 25m
Multiple Airlines
Deal found 6/27$1,267
This Kiwi.com deal was found by Cheapflights users on 6/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/39:00 pm
KIX
-
ORD
2 stops41h 49m
Multiple Airlines
Sun 9/1311:50 am
ORD
-
KIX
1 stop19h 00m
Multiple Airlines
Deal found 6/26$1,270
This Kiwi.com deal was found by Cheapflights users on 6/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/12:35 pm
ITM
-
ORD
2 stops29h 42m
Multiple Airlines
Thu 9/105:45 pm
ORD
-
ITM
1 stop24h 20m
Multiple Airlines
Deal found 6/27$1,272
This Kiwi.com deal was found by Cheapflights users on 6/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/27:35 am
KIX
-
ORD
2 stops22h 24m
Multiple Airlines
Thu 9/1011:50 am
ORD
-
KIX
1 stop19h 00m
Multiple Airlines
Deal found 6/27$1,273
This Kiwi.com deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” 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 9/12:35 pm
ITM
-
ORD
2 stops29h 42m
Multiple Airlines
Tue 9/85:45 pm
ORD
-
ITM
1 stop23h 40m
Multiple Airlines
Deal found 6/24$1,285
This Qatar Airways deal was found by Cheapflights users on 6/27. 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 Qatar Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/226:55 pm
KIX
-
ORD
1 stop34h 10m
Qatar Airways
Wed 10/287:50 pm
ORD
-
KIX
1 stop30h 35m
Qatar Airways
Deal found 6/27$1,313

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 June 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$1,195
(Kiwi.com)

One-way from

$504
(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)
Search Deals
One-way flight from Osaka (OSA) to Chicago (CHI)
Search Deals

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 June 29, 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 9/1

9:00 pm-3:59 pm

2 stops32h 59m

Chicago O'Hare Intl

Tue 9/8

11:50 am-8:50 pm

1 stop19h 00m

$1,195

OsakaChicago

KIX - ORD

KIXORD

Osaka Kansai Intl

Thu 11/12

5:55 pm-2:30 pm

1 stop35h 35m

Chicago O'Hare Intl

Sun 11/15

6:50 pm-4:25 pm

1 stop30h 35m

$1,360

OsakaChicago

KIX - ORD

KIXORD

Osaka Kansai Intl

Tue 9/22

1:10 pm-8:45 pm

1 stop21h 35m

Chicago O'Hare Intl

Sun 9/27

12:30 am-12:10 pm

1 stop21h 40m

$1,435

OsakaChicago

KIX - ORD

KIXORD

Osaka Kansai Intl

Wed 9/23

1:10 pm-8:45 pm

1 stop21h 35m

Chicago O'Hare Intl

Mon 9/28

12:30 am-5:15 pm

1 stop26h 45m

$1,435

OsakaChicago

KIX - ORD

KIXORD

Osaka Kansai Intl

Wed 9/23

11:10 am-8:45 pm

1 stop23h 35m

Chicago O'Hare Intl

Sun 9/27

12:30 am-12:10 pm

1 stop21h 40m

$1,436

OsakaChicago

KIX - ORD

KIXORD

Osaka Kansai Intl

Mon 8/10

9:00 pm-6:17 am

2 stops47h 17m

Chicago O'Hare Intl

Mon 8/17

11:50 am-8:50 pm

1 stop19h 00m

$1,442

OsakaChicago

KIX - ORD

KIXORD

Osaka Kansai Intl

Thu 11/12

4:15 pm-12:55 pm

2 stops35h 40m

Chicago O'Hare Intl

Sun 11/15

2:35 pm-2:55 pm

2 stops33h 20m

$1,444

OsakaChicago

KIX - ORD

KIXORD

Osaka Kansai Intl

Tue 8/11

7:45 am-6:17 am

2 stops36h 32m

Chicago O'Hare Intl

Sat 8/22

11:50 am-9:15 am

1 stop31h 25m

$1,464

OsakaChicago

KIX - ORD

KIXORD

Osaka Kansai Intl

Fri 10/9

9:45 am-1:55 pm

1 stop42h 10m

Chicago O'Hare Intl

Wed 10/14

4:15 pm-2:50 pm

2 stops32h 35m

$1,479

OsakaChicago

KIX - ORD

KIXORD

Osaka Kansai Intl

Tue 8/11

6:00 pm-2:36 pm

1 stop34h 36m

Chicago O'Hare Intl

Sat 8/22

3:40 pm-4:25 pm

1 stop34h 45m

$1,496

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/25

Showing 1-10 of 51 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 Itami - Chicago O'Hare Intl or Osaka Kansai Intl - Chicago Midway, 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
Hammond
Lansing
Merrillville
Valparaiso
Porter

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