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$451+ 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 9/23. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — OSA
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Osaka are usually found in October or September, booked 41 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 September 11, 2025.

Round-trip from

$744
(oojo)

One-way from

$451
(Mytrip)

Popular in

June

Cheapest in

October

Average price

$1,090
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. 11% potential increase in price ($180 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($30 potential savings vs. average RT price).
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Average for round-trip flights in September 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 September 11, 2025.

This oojo deal was found by Cheapflights users on 9/11. 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.
Mon 9/224:00 pmORD - KIX
1 stop24h 40mCathay Pacific
Tue 9/305:45 pmKIX - ORD
1 stop34h 40mCathay Pacific
Deal found 9/11$744
This lastminute.com deal was found by Cheapflights users on 9/11. 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 lastminute.com 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 9/306:35 pmKIX - ORD
1 stop33h 50mCathay Pacific
Deal found 9/11$750
This oojo deal was found by Cheapflights users on 9/10. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/283:40 pmORD - KIX
1 stop39h 25mCathay Pacific
Tue 11/44:55 pmKIX - ORD
1 stop35h 05mCathay Pacific
Deal found 9/10$751
This oojo deal was found by Cheapflights users on 9/11. 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.
Tue 9/164:00 pmORD - KIX
1 stop24h 40mCathay Pacific
Tue 9/235:45 pmKIX - ORD
1 stop34h 40mCathay Pacific
Deal found 9/11$760
This oojo deal was found by Cheapflights users on 9/11. 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 10/24:00 pmORD - KIX
1 stop36h 10mCathay Pacific
Wed 10/154:20 pmKIX - ORD
2 stops36h 05mCathay Pacific
Deal found 9/11$761
This oojo deal was found by Cheapflights users on 9/11. 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.
Wed 10/14:00 pmORD - KIX
1 stop33h 15mCathay Pacific
Wed 10/154:20 pmKIX - ORD
2 stops36h 05mCathay Pacific
Deal found 9/11$768
This Gurufare deal was found by Cheapflights users on 9/10. 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 Gurufare is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/214:00 pmORD - KIX
1 stop31h 00mCathay Pacific
Wed 11/194:55 pmKIX - ORD
1 stop35h 05mCathay Pacific
Deal found 9/10$774
This Cathay Pacific deal was found by Cheapflights users on 9/10. 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 Cathay Pacific is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/214:00 pmORD - KIX
1 stop31h 00mCathay Pacific
Tue 11/186:05 pmKIX - ORD
1 stop33h 55mCathay Pacific
Deal found 9/10$779
This lol.travel deal was found by Cheapflights users on 9/10. 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 lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/32:40 pmORD - KIX
1 stop24h 40mCathay Pacific
Sat 11/154:05 pmKIX - ORD
2 stops35h 55mCathay Pacific
Deal found 9/10$782
This Cheapflightsfares deal was found by Cheapflights users on 9/10. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/191:05 amORD - ITM
1 stop18h 30mJapan Airlines
Fri 11/217:30 amITM - ORD
1 stop15h 00mJapan Airlines
Deal found 9/10$1,052
This Cheapflightsfares deal was found by Cheapflights users on 9/10. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/2012:40 pmORD - UKB
1 stop19h 05mANA
Fri 11/217:05 amUKB - ORD
1 stop15h 15mANA
Deal found 9/10$1,082
This Cheapflightsfares deal was found by Cheapflights users on 9/10. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/207:10 amORD - ITM
2 stops22h 00mANA
Fri 11/211:00 pmITM - ORD
1 stop17h 10mANA
Deal found 9/10$1,087

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 September 11, 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

Tue 2/24

2:40 pm-12:45 pm

1 stop31h 05m

Osaka Kansai Intl

Wed 3/4

9:50 am-1:00 pm

1 stop42h 10m

$751

ChicagoOsaka

ORD - KIX

ORDKIX

Chicago O'Hare Intl

Wed 10/22

4:00 pm-6:40 am

1 stop24h 40m

Osaka Kansai Intl

Sun 11/23

4:05 pm-1:00 pm

2 stops35h 55m

$795

ChicagoOsaka

ORD - KIX

ORDKIX

Chicago O'Hare Intl

Tue 10/21

4:00 pm-2:55 pm

2 stops32h 55m

Osaka Kansai Intl

Mon 11/24

4:55 pm-1:00 pm

1 stop35h 05m

$795

ChicagoOsaka

ORD - KIX

ORDKIX

Chicago O'Hare Intl

Thu 10/23

4:00 pm-2:55 pm

2 stops56h 55m

Osaka Kansai Intl

Sun 11/23

4:05 pm-1:00 pm

2 stops35h 55m

$831

ChicagoOsaka

ORD - KIX

ORDKIX

Chicago O'Hare Intl

Sun 10/19

4:00 pm-6:40 am

1 stop24h 40m

Osaka Kansai Intl

Mon 11/24

4:05 pm-1:00 pm

2 stops35h 55m

$845

ChicagoOsaka

ORD - KIX

ORDKIX

Chicago O'Hare Intl

Sun 10/19

4:00 pm-6:40 am

1 stop24h 40m

Osaka Kansai Intl

Tue 11/18

4:05 pm-1:00 pm

2 stops35h 55m

$845

ChicagoOsaka

ORD - ITM

ORDITM

Chicago O'Hare Intl

Sat 2/7

3:40 pm-6:55 pm

2 stops36h 15m

Osaka Itami

Sun 2/15

2:00 pm-7:30 pm

2 stops20h 30m

$1,021

ChicagoOsaka

ORD - ITM

ORDITM

Chicago O'Hare Intl

Mon 10/20

1:05 am-10:40 am

1 stop19h 35m

Osaka Itami

Thu 11/20

8:25 am-7:30 am

1 stop14h 05m

$1,095

ChicagoKobe

ORD - UKB

ORDUKB

Chicago O'Hare Intl

Sun 10/19

12:40 pm-9:45 pm

1 stop19h 05m

Kobe

Thu 11/20

7:05 am-7:20 am

1 stop15h 15m

$1,104

ChicagoKobe

ORD - UKB

ORDUKB

Chicago O'Hare Intl

Tue 10/21

12:40 pm-9:45 pm

1 stop19h 05m

Kobe

Thu 11/20

7:05 am-7:20 am

1 stop15h 15m

$1,104

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/10

Showing 1-10 of 52 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 29, 2025.

The best time to book flights from Chicago to Osaka is 39 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 $866). Flying from Chicago to Osaka in June is currently the most expensive (average of $1,310). 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 September 11, 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.

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 September 11, 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
1,236 reviews

Boarding

8.4

Crew

8.6

Entertainment

8.0

Overall

8.4

Comfort

8.3

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
1,236 reviews
EVA Air
8.4
Very good
1,236 reviews

Boarding

8.4

Crew

8.6

Entertainment

8.0

Overall

8.4

Comfort

8.3

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
961 reviews
EVA Air
8.4
Very good
1,236 reviews

Boarding

8.4

Crew

8.6

Entertainment

8.0

Overall

8.4

Comfort

8.3

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
1,559 reviews
EVA Air
8.4
Very good
1,236 reviews

Boarding

8.4

Crew

8.6

Entertainment

8.0

Overall

8.4

Comfort

8.3

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
993 reviews
EVA Air
8.4
Very good
1,236 reviews

Boarding

8.4

Crew

8.6

Entertainment

8.0

Overall

8.4

Comfort

8.3

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
10,000 reviews
EVA Air
8.4
Very good
1,236 reviews

Boarding

8.4

Crew

8.6

Entertainment

8.0

Overall

8.4

Comfort

8.3

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.

  • How long is the flight from Chicago to Osaka?

    Cathay Pacific, ANA, and Japan Airlines can get you from Chicago to Osaka in just under 19h 05m. Your travel time can differ by up to 5h 35m. The distance between Chicago and Osaka is about 6476 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 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 30% less than the average price by searching for these airlines.

  • What are the cheapest airlines to fly from Chicago to Osaka one-way?

    To fly one-way, consider booking your trip with Cathay Pacific, which is currently one of the cheapest options available, starting at $526. EVA Air flights start at $706 while deals on ANA start at $707 one-way.

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

    The most popular route from Chicago to Osaka is Chicago O'Hare Intl - Osaka Itami. You may also consider Chicago O'Hare Intl - Osaka Kansai Intl 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 $866). Flying from Chicago to Osaka in June is currently the most expensive (average of $1,310). 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 Itami flights
O'Hare Intl to Kansai Intl 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 September 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
ANACheapest$983Average$1,695FlexibilityNo 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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