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$476+ 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 8/23. Fares are subject to change and may not be available on all flights or dates of travel.
OSA — CHI
May 1 — May 81
Fri 5/1
Fri 5/8
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 April 1, 2026.

This EVA Air deal was found by Cheapflights users on 3/29. 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 EVA Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/56:10 pm
KIX
-
ORD
1 stop40h 25m
EVA Air
Mon 11/911:30 pm
ORD
-
KIX
1 stop19h 25m
EVA Air
Deal found 3/29$983
This Air Canada deal was found by Cheapflights users on 3/30. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/76:00 pm
KIX
-
ORD
1 stop34h 45m
Air Canada
Sat 5/307:42 pm
ORD
-
KIX
2 stops30h 43m
Air Canada
Deal found 3/30$1,082
This Priceline deal was found by Cheapflights users on 3/27. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/116:00 pm
KIX
-
ORD
1 stop34h 45m
Air Canada
Mon 5/1811:00 pm
ORD
-
KIX
2 stops51h 25m
Air Canada
Deal found 3/27$1,176
This Flightnetwork deal was found by Cheapflights users on 3/29. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/146:00 pm
KIX
-
ORD
2 stops20h 58m
Air Canada
Sat 5/162:00 pm
ORD
-
KIX
2 stops36h 25m
Air Canada
Deal found 3/29$1,202
This EVA Air deal was found by Cheapflights users on 3/29. 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 EVA Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/116:30 pm
KIX
-
MDW
2 stops25h 25m
Multiple Airlines
Sat 6/279:00 pm
MDW
-
KIX
2 stops23h 10m
Multiple Airlines
Deal found 3/29$1,235
This Air Canada deal was found by Cheapflights users on 3/29. 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.
Thu 11/52:00 pm
ITM
-
ORD
2 stops20h 35m
Air Canada
Mon 11/94:40 pm
ORD
-
ITM
2 stops35h 30m
Air Canada
Deal found 3/29$1,418
This Booking.com deal was found by Cheapflights users on 4/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/1512:55 pm
ITM
-
ORD
2 stops23h 06m
Air Canada
Sat 5/308:35 pm
ORD
-
ITM
2 stops31h 35m
Air Canada
Deal found 4/1$1,455
This American Airlines deal was found by Cheapflights users on 3/29. 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.
Thu 6/112:35 pm
ITM
-
ORD
2 stops19h 44m
American Airlines
Sat 6/278:50 pm
ORD
-
ITM
2 stops24h 45m
American Airlines
Deal found 3/29$1,465
This oojo deal was found by Cheapflights users on 3/27. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/112:35 pm
ITM
-
ORD
1 stop31h 10m
Japan Airlines
Mon 5/189:40 am
ORD
-
ITM
2 stops43h 00m
Japan Airlines
Deal found 3/27$1,489
This Ovago deal was found by Cheapflights users on 3/29. 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 Ovago is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/137:05 am
ITM
-
ORD
1 stop17h 55m
Japan Airlines
Wed 5/206:56 am
ORD
-
ITM
2 stops22h 54m
Japan Airlines
Deal found 3/29$1,506
This China Airlines deal was found by Cheapflights users on 3/31. 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.
Sat 5/167:05 pm
KIX
-
MDW
2 stops24h 35m
Multiple Airlines
Sat 5/236:10 pm
MDW
-
KIX
2 stops28h 40m
Multiple Airlines
Deal found 3/31$1,528
This JTB deal was found by Cheapflights users on 3/28. 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 JTB is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/122:35 pm
ITM
-
ORD
2 stops19h 39m
Japan Airlines
Tue 5/198:57 am
ORD
-
ITM
2 stops20h 53m
Japan Airlines
Deal found 3/28$1,581

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 April 1, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$1,082
(Air Canada)

One-way from

$476
(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 April 1, 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

Mon 5/11

6:00 pm-8:00 am

2 stops28h 00m

Chicago O'Hare Intl

Mon 5/18

11:00 pm-4:25 pm

2 stops51h 25m

$1,180

OsakaChicago

KIX - MDW

KIXMDW

Osaka Kansai Intl

Thu 6/11

6:30 pm-5:55 am

2 stops25h 25m

Chicago Midway

Sat 6/27

9:00 pm-10:10 am

2 stops23h 10m

$1,235

OsakaChicago

KIX - ORD

KIXORD

Osaka Kansai Intl

Thu 5/14

6:00 pm-12:58 am

2 stops20h 58m

Chicago O'Hare Intl

Thu 5/21

7:42 pm-4:25 pm

2 stops30h 43m

$1,252

OsakaChicago

KIX - ORD

KIXORD

Osaka Kansai Intl

Thu 5/14

6:00 pm-8:15 pm

1 stop16h 15m

Chicago O'Hare Intl

Sat 5/16

3:40 pm-4:25 pm

2 stops34h 45m

$1,299

OsakaChicago

KIX - ORD

KIXORD

Osaka Kansai Intl

Tue 5/12

6:00 pm-2:45 pm

1 stop34h 45m

Chicago O'Hare Intl

Tue 5/19

4:15 pm-4:25 pm

2 stops34h 10m

$1,403

OsakaChicago

KIX - ORD

KIXORD

Osaka Kansai Intl

Sat 5/16

6:30 pm-6:20 am

2 stops25h 50m

Chicago O'Hare Intl

Sat 5/23

7:49 pm-10:10 am

2 stops24h 21m

$1,449

OsakaChicago

ITM - ORD

ITMORD

Osaka Itami

Thu 6/11

2:35 pm-8:19 pm

2 stops19h 44m

Chicago O'Hare Intl

Sat 6/27

8:50 pm-11:35 am

2 stops24h 45m

$1,465

OsakaChicago

KIX - ORD

KIXORD

Osaka Kansai Intl

Wed 4/29

1:10 pm-6:05 am

2 stops30h 55m

Chicago O'Hare Intl

Wed 5/6

4:00 pm-5:15 pm

2 stops35h 15m

$1,472

OsakaChicago

KIX - ORD

KIXORD

Osaka Kansai Intl

Thu 6/11

12:35 pm-9:57 pm

2 stops23h 22m

Chicago O'Hare Intl

Sat 6/27

8:36 am-10:40 pm

2 stops24h 04m

$1,485

OsakaChicago

ITM - ORD

ITMORD

Osaka Itami

Mon 5/11

2:35 pm-7:45 am

1 stop31h 10m

Chicago O'Hare Intl

Mon 5/18

9:40 am-6:40 pm

2 stops43h 00m

$1,489

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/31

Showing 1-10 of 52 resultsSorted by cheapest first
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6
  • 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 19h 44m. 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 Kansai Intl - Chicago O'Hare Intl, Osaka Itami - 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
Lansing
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Hammond
Porter
Benton Harbor

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