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$499+ 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 12/4. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — OSA
Dec 24 — Dec 311
Wed 12/24
Wed 12/31
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Osaka are usually found in September or October, booked 56 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 November 24, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$759
(Cathay Pacific)

One-way from

$499
(Mytrip)

Popular in

December

Cheapest in

September

Average price

$1,412
Provider with most accurate pricing for Chicago (CHI)-Osaka (OSA) flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Osaka (OSA) flights.
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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. 4% potential increase in price ($66 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 November 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 November 24, 2025.

This oojo deal was found by Cheapflights users on 11/23. 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.
Thu 11/2711:30 pmORD - KIX
1 stop19h 25mEVA Air
Thu 12/412:55 pmKIX - ORD
1 stop21h 40mEVA Air
Deal found 11/23$971
This Kiwi.com deal was found by Cheapflights users on 11/23. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/274:25 pmORD - KIX
1 stop25h 10mMultiple Airlines
Thu 12/48:00 amKIX - ORD
2 stops37h 05mMultiple Airlines
Deal found 11/23$1,002
This oojo deal was found by Cheapflights users on 11/23. 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.
Thu 11/2711:30 pmORD - KIX
1 stop21h 25mEVA Air
Sun 12/710:55 amKIX - ORD
1 stop23h 40mEVA Air
Deal found 11/23$1,009
This oojo deal was found by Cheapflights users on 11/23. 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.
Thu 11/272:35 pmORD - KIX
2 stops33h 20mCathay Pacific
Thu 12/44:15 pmKIX - ORD
2 stops35h 40mCathay Pacific
Deal found 11/23$1,027
This Air Canada deal was found by Cheapflights users on 11/23. 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.
Tue 11/258:00 amORD - ITM
2 stops20h 10mAir Canada
Tue 12/24:00 pmITM - ORD
2 stops18h 30mAir Canada
Deal found 11/23$1,053
This Kiwi.com deal was found by Cheapflights users on 11/22. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/76:50 amORD - KIX
1 stop21h 00mMultiple Airlines
Sat 12/139:10 pmKIX - ORD
2 stops47h 55mMultiple Airlines
Deal found 11/22$1,110
This Expedia deal was found by Cheapflights users on 11/23. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/18:00 amORD - ITM
2 stops21h 20mMultiple Airlines
Sun 12/77:05 amITM - ORD
2 stops27h 25mMultiple Airlines
Deal found 11/23$1,161
This Mytrip deal was found by Cheapflights users on 11/23. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/257:05 amORD - ITM
2 stops21h 45mMultiple Airlines
Tue 12/22:40 pmITM - ORD
3 stops32h 23mMultiple Airlines
Deal found 11/23$1,175
This Gotogate deal was found by Cheapflights users on 11/23. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/2910:30 amORD - ITM
1 stop17h 25mANA
Wed 1/142:05 pmITM - ORD
1 stop14h 45mANA
Deal found 11/23$1,197
This Mytrip deal was found by Cheapflights users on 11/23. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/278:00 amORD - UKB
2 stops22h 45mMultiple Airlines
Thu 12/411:10 amUKB - ORD
2 stops33h 55mMultiple Airlines
Deal found 11/23$1,206
This Air Canada deal was found by Cheapflights users on 11/23. 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.
Mon 12/18:00 amORD - ITM
2 stops21h 20mAir Canada
Mon 1/122:05 pmITM - ORD
2 stops21h 05mAir Canada
Deal found 11/23$1,208
This Gotogate deal was found by Cheapflights users on 11/23. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/297:05 amORD - KIX
1 stop18h 35mANA
Wed 1/149:10 pmKIX - ORD
1 stop25h 10mANA
Deal found 11/23$1,210

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 November 24, 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 1/12

2:35 pm-5:50 pm

1 stop36h 15m

Osaka Kansai Intl

Mon 1/26

10:00 am-12:55 pm

1 stop41h 55m

$759

ChicagoOsaka

ORD - KIX

ORDKIX

Chicago O'Hare Intl

Mon 1/12

2:35 pm-3:15 pm

1 stop33h 40m

Osaka Kansai Intl

Wed 1/21

10:00 am-12:55 pm

1 stop41h 55m

$760

ChicagoOsaka

ORD - KIX

ORDKIX

Chicago O'Hare Intl

Thu 2/5

2:35 pm-9:05 pm

1 stop39h 30m

Osaka Kansai Intl

Thu 2/12

6:05 pm-12:55 pm

1 stop33h 50m

$810

ChicagoOsaka

ORD - KIX

ORDKIX

Chicago O'Hare Intl

Sat 2/7

2:35 pm-3:15 pm

1 stop33h 40m

Osaka Kansai Intl

Wed 2/25

9:25 am-12:55 pm

1 stop42h 30m

$810

ChicagoOsaka

ORD - KIX

ORDKIX

Chicago O'Hare Intl

Mon 1/12

2:35 pm-2:55 pm

2 stops33h 20m

Osaka Kansai Intl

Fri 1/23

6:05 pm-12:55 pm

1 stop33h 50m

$826

ChicagoOsaka

ORD - ITM

ORDITM

Chicago O'Hare Intl

Fri 1/23

3:35 pm-6:55 pm

2 stops36h 20m

Osaka Itami

Sat 1/31

4:00 pm-7:45 pm

2 stops18h 45m

$954

ChicagoOsaka

ORD - ITM

ORDITM

Chicago O'Hare Intl

Fri 1/16

8:00 am-8:20 pm

2 stops21h 20m

Osaka Itami

Sat 1/24

3:00 pm-7:45 pm

2 stops19h 45m

$963

ChicagoOsaka

ORD - ITM

ORDITM

Chicago O'Hare Intl

Mon 1/12

4:25 pm-9:10 am

1 stop25h 45m

Osaka Itami

Mon 1/26

8:20 pm-7:20 am

1 stop26h 00m

$971

ChicagoKobe

ORD - UKB

ORDUKB

Chicago O'Hare Intl

Mon 1/12

4:25 pm-8:00 am

1 stop24h 35m

Kobe

Mon 1/26

9:15 pm-3:10 pm

1 stop32h 55m

$971

ChicagoOsaka

ORD - ITM

ORDITM

Chicago O'Hare Intl

Sun 1/11

10:30 am-8:20 pm

1 stop18h 50m

Osaka Itami

Mon 1/26

8:20 pm-7:20 am

1 stop26h 00m

$972

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/22

Showing 1-10 of 60 results
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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 November.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
AranGrantPrice Accuracy2 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 eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Chicago-Osaka flight deals on Cheapflights vs. eDreams >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 eDreams the most. eDreams 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

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 November 21, 2025.

The best time to book flights from Chicago to Osaka is 56 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, September is the cheapest month in which you can book a flight from Chicago to Osaka (average of $801). Flying from Chicago to Osaka in August is currently the most expensive (average of $1,691). 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 November 24, 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 27% versus a flight in the evening.

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.

Taipei City (TPE) – chosen by Cheapflights users on 50% 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.

Taipei City (TPE) is the most affordable 1-stop option, with an average round-trip price of $1,074.

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.

How often are flights from Chicago to Osaka delayed?

About 28% of weekly flights between Chicago and Osaka have experienced delays in the past year, with the average delay time being 122 minutes.

What is the most punctual flight time for Chicago to Osaka flights?

Historically, flights departing in the evening 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?

Friday tends to have the lowest number of delays on this route, whereas Thursday 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 25% 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 November 24, 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
1,283 reviews

Boarding

8.4

Entertainment

8.0

Food

8.1

Comfort

8.3

Overall

8.4

Crew

8.6

Reviews

1 / 20
10.0
Excellent

Walter,Nov 2025

LAX - TPE

Everything went well. The crew was very friendly and efficient and they made a long flight enjoyable.
EVA Air
8.4
Very good
1,283 reviews
EVA Air
8.4
Very good
1,283 reviews

Boarding

8.4

Entertainment

8.0

Food

8.1

Comfort

8.3

Overall

8.4

Crew

8.6

Reviews

1 / 20
10.0
Excellent

Walter,Nov 2025

LAX - TPE

Everything went well. The crew was very friendly and efficient and they made a long flight enjoyable.
ANA
8.4
Very good
1,010 reviews
EVA Air
8.4
Very good
1,283 reviews

Boarding

8.4

Entertainment

8.0

Food

8.1

Comfort

8.3

Overall

8.4

Crew

8.6

Reviews

1 / 20
10.0
Excellent

Walter,Nov 2025

LAX - TPE

Everything went well. The crew was very friendly and efficient and they made a long flight enjoyable.
Japan Airlines
8.3
Very good
1,627 reviews
EVA Air
8.4
Very good
1,283 reviews

Boarding

8.4

Entertainment

8.0

Food

8.1

Comfort

8.3

Overall

8.4

Crew

8.6

Reviews

1 / 20
10.0
Excellent

Walter,Nov 2025

LAX - TPE

Everything went well. The crew was very friendly and efficient and they made a long flight enjoyable.
Cathay Pacific
7.6
Good
1,068 reviews
EVA Air
8.4
Very good
1,283 reviews

Boarding

8.4

Entertainment

8.0

Food

8.1

Comfort

8.3

Overall

8.4

Crew

8.6

Reviews

1 / 20
10.0
Excellent

Walter,Nov 2025

LAX - TPE

Everything went well. The crew was very friendly and efficient and they made a long flight enjoyable.
Air Canada
7.1
Good
10,469 reviews
EVA Air
8.4
Very good
1,283 reviews

Boarding

8.4

Entertainment

8.0

Food

8.1

Comfort

8.3

Overall

8.4

Crew

8.6

Reviews

1 / 20
10.0
Excellent

Walter,Nov 2025

LAX - TPE

Everything went well. The crew was very friendly and efficient and they made a long flight enjoyable.

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, Air Canada, and ANA can get you from Chicago to Osaka in just under 25h 45m. Your travel time can differ by up to 10h 35m. 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 Air Canada. Our recent data shows that you can find tickets from as low as $1,025 on this airline. Additional options worth looking into are EVA Air and ANA, starting at $1,097 and $1,173 round-trip. You may be able to fly from Chicago to Osaka for 29% 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 Japan Airlines, which is currently one of the cheapest options available, starting at $657. ANA flights start at $683 while deals on American Airlines start at $692 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 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, September is the cheapest month in which you can book a flight from Chicago to Osaka (average of $801). Flying from Chicago to Osaka in August is currently the most expensive (average of $1,691). 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 Osaka 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 November 24, 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$1,025Average$1,391FlexibilityNo cancel feeOn-time67%
EVA AirCheapest$1,097Average$1,293FlexibilityNo cancel feeOn-time74%
ANACheapest$1,173Average$1,695FlexibilityNo cancel feeOn-time80%
United AirlinesCheapest$1,570Average$1,996FlexibilityNo cancel feeOn-time69%

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