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$435+ 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 8/25. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — OSA
Aug 22 — Aug 291
Sat 8/22
Sat 8/29
1 adult, Economy
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Cheap flight deals from Chicago to Osaka

Cheapest flights from Chicago to Osaka
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 July 23, 2026.

This Flightnetwork deal was found by Cheapflights users on 7/20. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/278:40 pm
ORD
-
KIX
1 stop29h 45m
Air Canada
Wed 8/126:00 pm
KIX
-
ORD
1 stop29h 00m
Air Canada
Deal found 7/20$866
This Air Canada deal was found by Cheapflights users on 7/23. 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 7/315:00 am
ORD
-
KIX
2 stops21h 25m
Air Canada
Thu 8/136:00 pm
KIX
-
ORD
2 stops25h 03m
Air Canada
Deal found 7/23$913
This Trip.com deal was found by Cheapflights users on 7/23. 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.
Fri 11/1310:45 pm
ORD
-
KIX
1 stop29h 25m
Philippine Airlines
Sun 11/299:20 pm
KIX
-
ORD
1 stop34h 35m
Philippine Airlines
Deal found 7/23$963
This Kiwi.com deal was found by Cheapflights users on 7/21. 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.
Tue 9/2911:50 am
ORD
-
KIX
1 stop19h 00m
Multiple Airlines
Wed 10/77:35 am
KIX
-
ORD
2 stops27h 59m
Multiple Airlines
Deal found 7/21$986
This Kiwi.com deal was found by Cheapflights users on 7/20. 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 8/2611:50 am
ORD
-
KIX
1 stop19h 00m
Multiple Airlines
Tue 10/68:05 pm
KIX
-
ORD
2 stops39h 29m
Multiple Airlines
Deal found 7/20$987
This Flightnetwork deal was found by Cheapflights users on 7/20. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/2711:50 am
ORD
-
ITM
1 stop17h 05m
ANA
Wed 8/127:25 am
ITM
-
ORD
1 stop15h 15m
ANA
Deal found 7/20$1,082
This oojo deal was found by Cheapflights users on 7/22. 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 8/3112:30 am
ORD
-
UKB
1 stop19h 30m
EVA Air
Wed 9/167:00 pm
UKB
-
ORD
1 stop39h 45m
EVA Air
Deal found 7/22$1,110
This Traveloka deal was found by Cheapflights users on 7/19. 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 Traveloka is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/272:30 pm
ORD
-
ITM
1 stop15h 55m
Japan Airlines
Wed 8/128:00 pm
ITM
-
ORD
1 stop25h 45m
Japan Airlines
Deal found 7/19$1,125
This oojo deal was found by Cheapflights users on 7/20. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/42:30 pm
ORD
-
ITM
1 stop15h 55m
Japan Airlines
Mon 8/102:30 pm
ITM
-
ORD
1 stop34h 30m
Japan Airlines
Deal found 7/20$1,143
This oojo deal was found by Cheapflights users on 7/22. 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.
Wed 8/1910:40 am
ORD
-
ITM
1 stop19h 10m
Japan Airlines
Wed 8/266:25 pm
ITM
-
ORD
1 stop27h 20m
Japan Airlines
Deal found 7/22$1,144
This oojo deal was found by Cheapflights users on 7/23. 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 8/410:40 am
ORD
-
ITM
1 stop19h 05m
Japan Airlines
Tue 8/114:45 pm
ITM
-
ORD
1 stop29h 00m
Japan Airlines
Deal found 7/23$1,146
This Kiwi.com deal was found by Cheapflights users on 7/20. 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.
Sun 8/3011:50 am
ORD
-
ITM
1 stop17h 05m
ANA
Tue 9/82:00 pm
ITM
-
ORD
1 stop14h 55m
ANA
Deal found 7/20$1,147

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 July 23, 2026.

Most accurate provider

Ovago
3 stars

Most trusted provider

Ovago
3 stars

Round-trip from

$963
(Trip.com)

One-way from

$435
(Kiwi.com)

Popular in

December

Cheapest in

May

Average price

$1,145
Provider with most accurate pricing for Chicago (CHI)-Osaka (OSA) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Osaka (OSA) flights.
Search Deals
From Chicago (CHI) to Osaka (OSA)
Search Deals
One-way flight from Chicago (CHI) to Osaka (OSA)
Search Deals
Highest demand for flights based on searches. 15% potential increase in price ($243 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($64 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2026
Search Deals

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 2,558,603 searches. Data last updated July 23, 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

Price

Cheapest round-trip

ChicagoOsaka

MDW - KIX

MDWKIX

Chicago Midway

Mon 8/31

9:59 am-10:40 pm

2 stops22h 41m

Osaka Kansai Intl

Fri 9/11

9:05 am-10:44 pm

2 stops27h 39m

$1,182

ChicagoOsaka

MDW - KIX

MDWKIX

Chicago Midway

Mon 8/31

9:59 am-10:40 pm

2 stops22h 41m

Osaka Kansai Intl

Wed 9/9

12:35 pm-10:44 pm

2 stops24h 09m

$1,182

ChicagoOsaka

ORD - KIX

ORDKIX

Chicago O'Hare Intl

Wed 8/26

5:00 am-2:50 pm

2 stops19h 50m

Osaka Kansai Intl

Tue 10/6

4:55 pm-10:46 pm

2 stops19h 51m

$1,223

ChicagoOsaka

ORD - ITM

ORDITM

Chicago O'Hare Intl

Mon 8/31

10:40 am-5:35 pm

1 stop16h 55m

Osaka Itami

Sat 9/12

8:05 pm-7:20 am

1 stop25h 15m

$1,231

ChicagoOsaka

ORD - KIX

ORDKIX

Chicago O'Hare Intl

Mon 8/31

6:00 am-2:50 pm

1 stop18h 50m

Osaka Kansai Intl

Sat 9/12

4:55 pm-8:26 pm

1 stop17h 31m

$1,231

ChicagoOsaka

ORD - KIX

ORDKIX

Chicago O'Hare Intl

Thu 8/13

5:00 am-2:50 pm

2 stops19h 50m

Osaka Kansai Intl

Wed 8/26

4:55 pm-8:26 pm

1 stop17h 31m

$1,231

ChicagoOsaka

MDW - KIX

MDWKIX

Chicago Midway

Mon 7/27

6:00 am-8:45 pm

2 stops24h 45m

Osaka Kansai Intl

Tue 8/11

2:15 am-12:39 pm

2 stops24h 24m

$1,232

ChicagoOsaka

MDW - KIX

MDWKIX

Chicago Midway

Thu 8/27

9:59 am-10:40 pm

2 stops22h 41m

Osaka Kansai Intl

Mon 8/31

12:35 pm-10:36 pm

2 stops24h 01m

$1,295

ChicagoOsaka

MDW - KIX

MDWKIX

Chicago Midway

Wed 8/12

9:00 pm-10:10 am

2 stops23h 10m

Osaka Kansai Intl

Wed 8/19

6:30 pm-5:50 am

2 stops25h 20m

$1,340

ChicagoKobe

ORD - UKB

ORDUKB

Chicago O'Hare Intl

Mon 8/31

12:30 am-10:00 am

1 stop19h 30m

Kobe

Thu 9/10

7:00 pm-8:45 pm

1 stop39h 45m

$1,351

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/20

Showing 1-10 of 60 resultsSorted by cheapest first
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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 July.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
AranGrantPrice Accuracy3 starsTrust Score*3 stars
OvagoPrice Accuracy3 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • 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.
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

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 $1,067). Flying from Chicago to Osaka in July is currently the most expensive (average of $1,822). 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 $1,024 and $1,100 in November.
The cheapest round-trip price found within the last 5 days was $963 on Philippine Airlines (Nov 13-Nov 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 35% of weekly flights between Chicago and Osaka have experienced delays in the past year, with the average delay time being 159 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 Sunday 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 33% 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 July 23, 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.
EVA Air
8.5
Very good
1,502 reviews

Overall

8.5

Comfort

8.3

Crew

8.7

Food

8.1

Boarding

8.4

Entertainment

8.0

Reviews

1 / 20
10.0
Excellent

Daisy,May 2026

SFO - TPE

This ways excellent experience when I took the EVA airline. We will take EVA again!
EVA Air
8.5
Very good
1,502 reviews
EVA Air
8.5
Very good
1,502 reviews

Overall

8.5

Comfort

8.3

Crew

8.7

Food

8.1

Boarding

8.4

Entertainment

8.0

Reviews

1 / 20
10.0
Excellent

Daisy,May 2026

SFO - TPE

This ways excellent experience when I took the EVA airline. We will take EVA again!
Japan Airlines
8.3
Very good
1,881 reviews
EVA Air
8.5
Very good
1,502 reviews

Overall

8.5

Comfort

8.3

Crew

8.7

Food

8.1

Boarding

8.4

Entertainment

8.0

Reviews

1 / 20
10.0
Excellent

Daisy,May 2026

SFO - TPE

This ways excellent experience when I took the EVA airline. We will take EVA again!
ANA
8.3
Very good
1,276 reviews
EVA Air
8.5
Very good
1,502 reviews

Overall

8.5

Comfort

8.3

Crew

8.7

Food

8.1

Boarding

8.4

Entertainment

8.0

Reviews

1 / 20
10.0
Excellent

Daisy,May 2026

SFO - TPE

This ways excellent experience when I took the EVA airline. We will take EVA again!
Cathay Pacific
7.6
Good
1,425 reviews
EVA Air
8.5
Very good
1,502 reviews

Overall

8.5

Comfort

8.3

Crew

8.7

Food

8.1

Boarding

8.4

Entertainment

8.0

Reviews

1 / 20
10.0
Excellent

Daisy,May 2026

SFO - TPE

This ways excellent experience when I took the EVA airline. We will take EVA again!
United Airlines
7.4
Good
10,024 reviews
EVA Air
8.5
Very good
1,502 reviews

Overall

8.5

Comfort

8.3

Crew

8.7

Food

8.1

Boarding

8.4

Entertainment

8.0

Reviews

1 / 20
10.0
Excellent

Daisy,May 2026

SFO - TPE

This ways excellent experience when I took the EVA airline. We will take EVA again!

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.

  • How long is the flight from Chicago to Osaka?

    Delta, United Airlines, and Japan Airlines can get you from Chicago to Osaka in just under 16h 55m. Your travel time can differ by up to 5h 46m. The distance between Chicago and Osaka is about 6461 mi. This flight may include one or multiple stops.

  • What are the cheapest airlines flying from Chicago to Osaka round-trip?

    Our cheapest airline available from Chicago to Osaka is EVA Air. Our recent data shows that you can find tickets from as low as $1,008 on this airline. Additional options worth looking into are Japan Airlines and United Airlines, starting at $1,039 and $1,145 round-trip. You may be able to fly from Chicago to Osaka for 21% less than the average price by searching for these airlines.

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

    The most popular route from Chicago to Osaka is Chicago O'Hare Intl - Osaka Kansai Intl. You may also consider Chicago O'Hare Intl - Osaka Itami or Chicago O'Hare Intl - Kobe.

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

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

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

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

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

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

  • 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 $1,067). Flying from Chicago to Osaka in July is currently the most expensive (average of $1,822). 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.

See more FAQs

Traveling to a place near Osaka?

Book flights to Osaka if you plan to visit one of these locations
Nara

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Alternative routes for Chicago to Osaka

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Kansai Intl flights
O'Hare Intl to Osaka Itami flights
St. Louis to Kansai Intl flights

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 2,558,603 searches. Data last updated July 23, 2026.
AirlineCheapestAverageFlexibilityOn-time
EVA AirCheapest$1,008Average$1,107FlexibilityNo cancel feeOn-time74%
Japan AirlinesCheapest$1,039Average$1,536FlexibilityNo cancel feeOn-time79%
United AirlinesCheapest$1,145Average$1,880FlexibilityNo cancel feeOn-time69%
ANACheapest$1,162Average$1,926FlexibilityNo cancel feeOn-time80%

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