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$440+ 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 9/15. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — OSA
Aug 19 — Aug 261
Tue 8/19
Tue 8/26
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Osaka are usually found in October or September, booked 84 days in advance, depart on a Tuesday or Wednesday and return on a Monday

Cheap 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 August 14, 2025.

Round-trip from

$675
(oojo)

One-way from

$440
(Trip.com)

Popular in

August

Cheapest in

October

Average price

$1,948
From Chicago (CHI) to Osaka (OSA)
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One-way flight from Chicago (CHI) to Osaka (OSA)
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Highest demand for flights based on searches. 2% potential increase in price ($42 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($48 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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Find 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 August 14, 2025.

This oojo deal was found by Cheapflights users on 8/13. 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 11/32:40 pmORD - KIX
1 stop39h 25mCathay Pacific
Mon 11/249:25 amKIX - ORD
1 stop42h 35mCathay Pacific
Deal found 8/13$675
This oojo deal was found by Cheapflights users on 8/12. 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.
Tue 10/283:40 pmORD - KIX
1 stop24h 40mCathay Pacific
Tue 11/49:50 amKIX - ORD
1 stop42h 10mCathay Pacific
Deal found 8/12$677
This lol.travel deal was found by Cheapflights users on 8/14. 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 lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/154:00 pmORD - KIX
1 stop24h 40mCathay Pacific
Tue 9/307:35 pmKIX - ORD
1 stop32h 50mCathay Pacific
Deal found 8/14$679
This oojo deal was found by Cheapflights users on 8/12. 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.
Tue 8/264:00 pmORD - KIX
1 stop24h 40mCathay Pacific
Tue 9/910:00 amKIX - ORD
1 stop42h 25mCathay Pacific
Deal found 8/12$691
This oojo deal was found by Cheapflights users on 8/14. 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 9/154:00 pmORD - KIX
1 stop24h 40mCathay Pacific
Wed 9/2410:00 amKIX - ORD
1 stop42h 25mCathay Pacific
Deal found 8/14$692
This Mytrip deal was found by Cheapflights users on 8/14. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/154:00 pmORD - KIX
1 stop24h 40mCathay Pacific
Sun 9/2810:00 amKIX - ORD
1 stop42h 25mCathay Pacific
Deal found 8/14$699
This oojo deal was found by Cheapflights users on 8/14. 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 9/224:00 pmORD - KIX
2 stops32h 55mCathay Pacific
Tue 9/306:35 pmKIX - ORD
1 stop33h 50mCathay Pacific
Deal found 8/14$709
This oojo deal was found by Cheapflights users on 8/13. 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 10/283:40 pmORD - KIX
2 stops33h 15mCathay Pacific
Tue 11/254:05 pmKIX - ORD
2 stops35h 55mCathay Pacific
Deal found 8/13$710
This oojo deal was found by Cheapflights users on 8/13. 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 11/202:40 pmORD - KIX
1 stop39h 25mCathay Pacific
Thu 11/276:05 pmKIX - ORD
1 stop33h 55mCathay Pacific
Deal found 8/13$718
This Trip.com deal was found by Cheapflights users on 8/12. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/116:30 amORD - UKB
2 stops45h 10mMultiple Airlines
Thu 9/1811:10 amUKB - ORD
2 stops25h 33mMultiple Airlines
Deal found 8/12$857
This lol.travel deal was found by Cheapflights users on 8/14. 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 lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/156:15 amORD - ITM
2 stops20h 50mUnited Airlines
Tue 9/3012:00 pmITM - ORD
1 stop16h 55mUnited Airlines
Deal found 8/14$870
This Cheapflightsfares deal was found by Cheapflights users on 8/14. 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.
Mon 9/155:45 pmORD - UKB
1 stop24h 05mANA
Wed 9/249:15 pmUKB - ORD
1 stop25h 25mANA
Deal found 8/14$895

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 August 14, 2025.
Use the filters below to find and compare flights from Chicago to Osaka that are best for you.

Fly from

Chicago

Fly to

Osaka

Route

Depart

Return

Price

ChicagoOsaka

ORD - KIX

ORDKIX

Chicago O'Hare Intl

Mon 11/3

2:40 pm-9:05 pm

1 stop39h 25m

Osaka Kansai Intl

Mon 11/24

9:25 am-1:00 pm

1 stop42h 35m

$675

ChicagoOsaka

ORD - KIX

ORDKIX

Chicago O'Hare Intl

Thu 11/6

2:40 pm-9:05 pm

1 stop39h 25m

Osaka Kansai Intl

Mon 12/1

9:25 am-1:00 pm

1 stop42h 35m

$677

ChicagoOsaka

ORD - KIX

ORDKIX

Chicago O'Hare Intl

Tue 8/19

4:00 pm-6:40 am

1 stop24h 40m

Osaka Kansai Intl

Sun 10/5

7:35 pm-2:25 pm

1 stop32h 50m

$677

ChicagoOsaka

ORD - KIX

ORDKIX

Chicago O'Hare Intl

Tue 10/28

3:40 pm-12:45 pm

1 stop31h 05m

Osaka Kansai Intl

Mon 11/24

6:05 pm-1:00 pm

1 stop33h 55m

$677

ChicagoOsaka

ORD - KIX

ORDKIX

Chicago O'Hare Intl

Tue 10/28

3:40 pm-6:20 am

1 stop24h 40m

Osaka Kansai Intl

Sun 11/23

4:55 pm-1:00 pm

1 stop35h 05m

$677

ChicagoOsaka

ORD - KIX

ORDKIX

Chicago O'Hare Intl

Mon 9/22

4:00 pm-6:40 am

1 stop24h 40m

Osaka Kansai Intl

Tue 9/30

7:35 pm-2:25 pm

1 stop32h 50m

$677

ChicagoOsaka

ORD - KIX

ORDKIX

Chicago O'Hare Intl

Tue 10/28

3:40 pm-9:05 pm

1 stop39h 25m

Osaka Kansai Intl

Tue 11/25

9:25 am-1:00 pm

1 stop42h 35m

$677

ChicagoOsaka

ORD - KIX

ORDKIX

Chicago O'Hare Intl

Thu 10/9

4:00 pm-9:15 pm

1 stop39h 15m

Osaka Kansai Intl

Tue 12/16

9:25 am-1:00 pm

1 stop42h 35m

$677

ChicagoOsaka

ORD - KIX

ORDKIX

Chicago O'Hare Intl

Tue 10/28

3:40 pm-6:20 am

1 stop24h 40m

Osaka Kansai Intl

Tue 11/4

9:50 am-1:00 pm

1 stop42h 10m

$677

ChicagoKobe

ORD - UKB

ORDUKB

Chicago O'Hare Intl

Thu 9/11

6:30 am-5:40 pm

2 stops45h 10m

Kobe

Thu 9/18

11:10 am-10:43 pm

2 stops25h 33m

$857

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/12

Showing 1-10 of 60 results
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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

How far ahead should I book a flight from Chicago to Osaka?

Use this chart to determine the optimal time to book a round-trip flight from Chicago to Osaka. Price data was last updated on August 8, 2025.

The best time to book flights from Chicago to Osaka is 84 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

What is the cheapest month to book a flight from Chicago to Osaka?

Currently, February is the cheapest month in which you can book a flight from Chicago to Osaka (average of $873). Flying from Chicago to Osaka in June is currently the most expensive (average of $1,313). 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.

What is the cheapest time of day to fly from CHI to OSA?

Find hourly flight availability from Chicago to Osaka. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated August 14, 2025.

When flying from Chicago to Osaka, the time of day you fly usually plays a role in the price. Save by searching for a flight in the afternoon, which can drop the price by up to 37% versus a flight at noon.

How much does it cost to fly round-trip from Chicago to Osaka?

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.

Istanbul (IST) – chosen by Cheapflights users on 60% 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.

Istanbul (IST) is the most affordable 1-stop option, with an average round-trip price of $756.

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 40m.

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 4h 03m.

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 August 14, 2025.
Read reviews from past customers who have flown EVA Air, ANA, and Japan Airlines 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
8.4
Very good
1,233 reviews

Boarding

8.4

Overall

8.4

Entertainment

8.0

Comfort

8.3

Crew

8.6

Food

8.1

Reviews

1 / 20
6.0
Good

Anonymous,Aug 2025

BKK - TPE

I bought tickets for myself and my friend and had to argue with the checkin person to get our seats together for the return flights I purchased the tickets together weeks ahead of time and did not expect to have to ask for a supervisor to sit together very disappointed in booking through kayak
EVA Air
8.4
Very good
1,233 reviews
EVA Air
8.4
Very good
1,233 reviews

Boarding

8.4

Overall

8.4

Entertainment

8.0

Comfort

8.3

Crew

8.6

Food

8.1

Reviews

1 / 20
6.0
Good

Anonymous,Aug 2025

BKK - TPE

I bought tickets for myself and my friend and had to argue with the checkin person to get our seats together for the return flights I purchased the tickets together weeks ahead of time and did not expect to have to ask for a supervisor to sit together very disappointed in booking through kayak
ANA
8.4
Very good
933 reviews
EVA Air
8.4
Very good
1,233 reviews

Boarding

8.4

Overall

8.4

Entertainment

8.0

Comfort

8.3

Crew

8.6

Food

8.1

Reviews

1 / 20
6.0
Good

Anonymous,Aug 2025

BKK - TPE

I bought tickets for myself and my friend and had to argue with the checkin person to get our seats together for the return flights I purchased the tickets together weeks ahead of time and did not expect to have to ask for a supervisor to sit together very disappointed in booking through kayak
Japan Airlines
8.3
Very good
1,545 reviews
EVA Air
8.4
Very good
1,233 reviews

Boarding

8.4

Overall

8.4

Entertainment

8.0

Comfort

8.3

Crew

8.6

Food

8.1

Reviews

1 / 20
6.0
Good

Anonymous,Aug 2025

BKK - TPE

I bought tickets for myself and my friend and had to argue with the checkin person to get our seats together for the return flights I purchased the tickets together weeks ahead of time and did not expect to have to ask for a supervisor to sit together very disappointed in booking through kayak
Cathay Pacific
7.6
Good
968 reviews
EVA Air
8.4
Very good
1,233 reviews

Boarding

8.4

Overall

8.4

Entertainment

8.0

Comfort

8.3

Crew

8.6

Food

8.1

Reviews

1 / 20
6.0
Good

Anonymous,Aug 2025

BKK - TPE

I bought tickets for myself and my friend and had to argue with the checkin person to get our seats together for the return flights I purchased the tickets together weeks ahead of time and did not expect to have to ask for a supervisor to sit together very disappointed in booking through kayak
Air Canada
7.1
Good
9,949 reviews
EVA Air
8.4
Very good
1,233 reviews

Boarding

8.4

Overall

8.4

Entertainment

8.0

Comfort

8.3

Crew

8.6

Food

8.1

Reviews

1 / 20
6.0
Good

Anonymous,Aug 2025

BKK - TPE

I bought tickets for myself and my friend and had to argue with the checkin person to get our seats together for the return flights I purchased the tickets together weeks ahead of time and did not expect to have to ask for a supervisor to sit together very disappointed in booking through kayak

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.

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

    Our cheapest airline available from Chicago to Osaka is ANA. Our recent data shows that you can find tickets from as low as $983 on this airline. Additional options worth looking into are Air Canada and EVA Air, starting at $1,025 and $1,097 round-trip. You may be able to fly from Chicago to Osaka for 31% 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, February is the cheapest month in which you can book a flight from Chicago to Osaka (average of $873). Flying from Chicago to Osaka in June is currently the most expensive (average of $1,313). 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
Nishinomiya

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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 Itami flights
Midway to Kansai Intl 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 August 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
ANACheapest$983Average$1,698FlexibilityNo cancel feeOn-time80%
Air CanadaCheapest$1,025Average$1,391FlexibilityNo cancel feeOn-time67%
EVA AirCheapest$1,097Average$1,293FlexibilityNo cancel feeOn-time74%
United AirlinesCheapest$1,099Average$1,698FlexibilityNo cancel feeOn-time69%

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