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$301+ 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 12/5. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — OSA
Dec 6 — Dec 131
Sat 12/6
Sat 12/13
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 6, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$830
(Trip.com)

One-way from

$301
(Kiwi.com)

Popular in

December

Cheapest in

September

Average price

$1,372
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)
Search Deals
Highest demand for flights based on searches. 3% potential increase in price ($57 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($49 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 6, 2025.

This Trip.com deal was found by Cheapflights users on 11/5. 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 12/46:50 amORD - KIX
2 stops47h 05mMultiple Airlines
Mon 12/159:00 amKIX - ORD
2 stops30h 13mMultiple Airlines
Deal found 11/5$830
This Mytrip deal was found by Cheapflights users on 11/4. 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.
Sat 12/69:06 pmORD - KIX
2 stops32h 49mMultiple Airlines
Sat 12/1310:30 amKIX - ORD
2 stops34h 35mMultiple Airlines
Deal found 11/4$833
This Trip.com deal was found by Cheapflights users on 11/4. 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.
Sun 12/76:50 amORD - ITM
2 stops33h 40mMultiple Airlines
Sun 12/142:05 pmITM - ORD
2 stops25h 08mMultiple Airlines
Deal found 11/4$870
This Trip.com deal was found by Cheapflights users on 11/5. 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.
Sun 12/76:50 amORD - KIX
2 stops44h 55mMultiple Airlines
Sun 12/1412:55 pmKIX - ORD
1 stop21h 40mMultiple Airlines
Deal found 11/5$885
This Mytrip deal was found by Cheapflights users on 11/5. 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 11/244:58 pmORD - KIX
3 stops24h 42mMultiple Airlines
Sat 12/69:00 amKIX - ORD
3 stops26h 09mMultiple Airlines
Deal found 11/5$898
This lastminute.com deal was found by Cheapflights users on 11/6. 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.
Sat 11/292:35 pmORD - KIX
1 stop24h 45mCathay Pacific
Mon 12/157:05 pmKIX - ORD
1 stop32h 50mCathay Pacific
Deal found 11/6$900
This Mytrip deal was found by Cheapflights users on 11/5. 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 11/254:58 pmORD - KIX
3 stops34h 07mMultiple Airlines
Sat 12/610:30 amKIX - ORD
2 stops34h 35mMultiple Airlines
Deal found 11/5$903
This Trip.com deal was found by Cheapflights users on 11/4. 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.
Sun 12/79:06 pmORD - KIX
1 stop30h 44mMultiple Airlines
Thu 12/187:00 amKIX - ORD
2 stops38h 05mMultiple Airlines
Deal found 11/4$912
This Alaska Airlines deal was found by Cheapflights users on 11/4. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/78:55 amORD - KIX
2 stops42h 50mAlaska Airlines
Thu 12/188:45 pmKIX - ORD
2 stops38h 17mAlaska Airlines
Deal found 11/4$913
This Kiwi.com deal was found by Cheapflights users on 11/6. 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 12/24:25 pmORD - ITM
1 stop24h 05mMultiple Airlines
Sat 12/134:50 pmITM - ORD
2 stops46h 23mMultiple Airlines
Deal found 11/6$1,023
This Kiwi.com deal was found by Cheapflights users on 11/6. 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 12/24:25 pmORD - ITM
1 stop24h 05mMultiple Airlines
Sun 12/149:00 amITM - ORD
2 stops30h 13mMultiple Airlines
Deal found 11/6$1,024
This Trip.com deal was found by Cheapflights users on 11/4. 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.
Sun 12/72:01 pmMDW - KIX
2 stops37h 49mMultiple Airlines
Thu 12/185:50 pmKIX - MDW
2 stops43h 08mMultiple Airlines
Deal found 11/4$1,027

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 6, 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

Sat 12/6

9:06 pm-8:55 pm

2 stops32h 49m

Osaka Kansai Intl

Sat 12/13

9:00 am-8:09 pm

3 stops26h 09m

$881

ChicagoOsaka

ORD - KIX

ORDKIX

Chicago O'Hare Intl

Sun 12/7

8:55 am-6:45 pm

2 stops42h 50m

Osaka Kansai Intl

Thu 12/18

8:45 pm-8:02 pm

2 stops38h 17m

$913

ChicagoOsaka

ORD - KIX

ORDKIX

Chicago O'Hare Intl

Sun 12/7

6:50 am-6:50 pm

1 stop21h 00m

Osaka Kansai Intl

Sun 12/14

7:00 am-12:13 am

2 stops32h 13m

$919

ChicagoOsaka

ORD - KIX

ORDKIX

Chicago O'Hare Intl

Sat 11/29

2:35 pm-2:55 pm

2 stops33h 20m

Osaka Kansai Intl

Mon 12/15

7:05 pm-12:55 pm

1 stop32h 50m

$932

ChicagoOsaka

ORD - KIX

ORDKIX

Chicago O'Hare Intl

Mon 12/1

4:58 pm-8:40 am

3 stops24h 42m

Osaka Kansai Intl

Mon 12/8

10:30 am-6:05 am

2 stops34h 35m

$957

ChicagoKobe

ORD - UKB

ORDUKB

Chicago O'Hare Intl

Wed 2/4

4:25 pm-8:00 am

1 stop24h 35m

Kobe

Wed 2/25

7:05 am-7:20 am

1 stop15h 15m

$986

ChicagoOsaka

ORD - KIX

ORDKIX

Chicago O'Hare Intl

Mon 12/1

2:35 pm-6:20 am

1 stop24h 45m

Osaka Kansai Intl

Mon 12/8

10:00 am-12:55 pm

1 stop41h 55m

$1,000

ChicagoOsaka

MDW - KIX

MDWKIX

Chicago Midway

Sun 12/7

2:01 pm-6:50 pm

2 stops37h 49m

Osaka Kansai Intl

Thu 12/18

5:50 pm-9:58 pm

2 stops43h 08m

$1,027

ChicagoOsaka

ORD - ITM

ORDITM

Chicago O'Hare Intl

Sat 11/29

4:25 pm-7:30 am

1 stop24h 05m

Osaka Itami

Mon 12/15

9:00 am-6:05 am

2 stops36h 05m

$1,050

ChicagoOsaka

MDW - KIX

MDWKIX

Chicago Midway

Thu 12/4

8:05 am-6:50 pm

2 stops43h 45m

Osaka Kansai Intl

Mon 12/15

5:50 pm-8:46 am

2 stops29h 56m

$1,051

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/5

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
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars
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 October 31, 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, December is the cheapest month in which you can book a flight from Chicago to Osaka (average of $756). 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 6, 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.

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 6, 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
1,272 reviews

Food

8.1

Entertainment

8.0

Comfort

8.3

Crew

8.6

Boarding

8.4

Overall

8.4

Reviews

1 / 20
10.0
Excellent

Anonymous,Oct 2025

TPE - YYZ

All was well. Despite the flight being delayed a few minutes, passengers were made sure to be informed and updated on the status of the delay.
EVA Air
8.4
Very good
1,272 reviews
EVA Air
8.4
Very good
1,272 reviews

Food

8.1

Entertainment

8.0

Comfort

8.3

Crew

8.6

Boarding

8.4

Overall

8.4

Reviews

1 / 20
10.0
Excellent

Anonymous,Oct 2025

TPE - YYZ

All was well. Despite the flight being delayed a few minutes, passengers were made sure to be informed and updated on the status of the delay.
ANA
8.4
Very good
1,003 reviews
EVA Air
8.4
Very good
1,272 reviews

Food

8.1

Entertainment

8.0

Comfort

8.3

Crew

8.6

Boarding

8.4

Overall

8.4

Reviews

1 / 20
10.0
Excellent

Anonymous,Oct 2025

TPE - YYZ

All was well. Despite the flight being delayed a few minutes, passengers were made sure to be informed and updated on the status of the delay.
Japan Airlines
8.3
Very good
1,604 reviews
EVA Air
8.4
Very good
1,272 reviews

Food

8.1

Entertainment

8.0

Comfort

8.3

Crew

8.6

Boarding

8.4

Overall

8.4

Reviews

1 / 20
10.0
Excellent

Anonymous,Oct 2025

TPE - YYZ

All was well. Despite the flight being delayed a few minutes, passengers were made sure to be informed and updated on the status of the delay.
Cathay Pacific
7.6
Good
1,055 reviews
EVA Air
8.4
Very good
1,272 reviews

Food

8.1

Entertainment

8.0

Comfort

8.3

Crew

8.6

Boarding

8.4

Overall

8.4

Reviews

1 / 20
10.0
Excellent

Anonymous,Oct 2025

TPE - YYZ

All was well. Despite the flight being delayed a few minutes, passengers were made sure to be informed and updated on the status of the delay.
Air Canada
7.1
Good
10,416 reviews
EVA Air
8.4
Very good
1,272 reviews

Food

8.1

Entertainment

8.0

Comfort

8.3

Crew

8.6

Boarding

8.4

Overall

8.4

Reviews

1 / 20
10.0
Excellent

Anonymous,Oct 2025

TPE - YYZ

All was well. Despite the flight being delayed a few minutes, passengers were made sure to be informed and updated on the status of the delay.

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?

    Alaska Airlines, Cathay Pacific, and ANA can get you from Chicago to Osaka in just under 24h 35m. Your travel time can differ by up to 18h 15m. 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 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 EVA Air, which is currently one of the cheapest options available, starting at $557. Japan Airlines flights start at $673 while deals on ANA start at $685 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 Midway - Osaka Kansai Intl.

  • 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, December is the cheapest month in which you can book a flight from Chicago to Osaka (average of $756). 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 6, 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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