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$493+ 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 1/5. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — OSA
Jan 7 — Jan 141
Wed 1/7
Wed 1/14
1 adult, Economy
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Find cheap flights from Chicago to Osaka with Cheapflights

1. Tell us where you want to go

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Cheapflights Tip: The best prices from Chicago to Osaka are usually found in May or September, booked 56 days in advance, depart on a Tuesday or Wednesday and return on a Monday

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 December 8, 2025.

This Gotogate deal was found by Cheapflights users on 12/6. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/72:35 pmORD - KIX
1 stop33h 40mCathay Pacific
Sat 12/136:05 pmKIX - ORD
1 stop33h 50mCathay Pacific
Deal found 12/6$1,090
This Mytrip deal was found by Cheapflights users on 12/6. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/78:00 amORD - KIX
2 stops23h 20mMultiple Airlines
Sat 12/137:50 amKIX - ORD
3 stops27h 19mMultiple Airlines
Deal found 12/6$1,347
This Gotogate deal was found by Cheapflights users on 12/6. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/92:35 pmORD - KIX
1 stop24h 45mMultiple Airlines
Thu 12/1110:55 amKIX - ORD
1 stop23h 40mMultiple Airlines
Deal found 12/6$1,461
This Air Canada deal was found by Cheapflights users on 12/6. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/78:00 amORD - ITM
2 stops21h 20mAir Canada
Sat 12/132:00 pmITM - ORD
2 stops20h 45mAir Canada
Deal found 12/6$1,463
This Mytrip deal was found by Cheapflights users on 12/6. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/97:05 amORD - ITM
2 stops21h 50mMultiple Airlines
Thu 12/112:40 pmITM - ORD
3 stops22h 25mMultiple Airlines
Deal found 12/6$1,517
This Mytrip deal was found by Cheapflights users on 12/6. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/79:06 pmORD - ITM
2 stops31h 49mMultiple Airlines
Sat 12/132:40 pmITM - ORD
3 stops30h 25mMultiple Airlines
Deal found 12/6$1,522
This oojo deal was found by Cheapflights users on 12/6. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/1011:30 pmORD - KIX
1 stop21h 25mEVA Air
Fri 12/126:10 pmKIX - ORD
1 stop40h 25mEVA Air
Deal found 12/6$1,540
This Booking.com deal was found by Cheapflights users on 12/7. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/138:30 pmORD - ITM
2 stops31h 40mAir Canada
Mon 12/222:00 pmITM - ORD
2 stops21h 10mAir Canada
Deal found 12/7$1,586
This Mytrip deal was found by Cheapflights users on 12/6. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/78:00 amORD - UKB
2 stops22h 45mMultiple Airlines
Sat 12/131:30 pmUKB - ORD
2 stops31h 35mMultiple Airlines
Deal found 12/6$1,588
This SmartFares deal was found by Cheapflights users on 12/6. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/103:35 pmORD - KIX
2 stops27h 20mMultiple Airlines
Fri 12/1212:55 pmKIX - ORD
1 stop21h 40mMultiple Airlines
Deal found 12/6$1,623
This Kiwi.com deal was found by Cheapflights users on 12/7. 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.
Sat 12/136:50 amORD - KIX
2 stops44h 55mMultiple Airlines
Mon 12/2212:55 pmKIX - ORD
1 stop21h 40mMultiple Airlines
Deal found 12/7$1,624
This Gotogate deal was found by Cheapflights users on 12/7. 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.
Thu 12/112:35 pmORD - KIX
2 stops33h 20mMultiple Airlines
Sat 12/136:10 pmKIX - ORD
1 stop40h 25mMultiple Airlines
Deal found 12/7$1,660

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 December 8, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$815
(Bravofly)

One-way from

$493
(Kiwi.com)

Popular in

December

Cheapest in

May

Average price

$1,926
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. 8% potential increase in price ($130 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($50 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
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 December 8, 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 1/20

2:35 pm-6:20 am

1 stop24h 45m

Osaka Kansai Intl

Tue 1/27

7:05 pm-12:55 pm

1 stop32h 50m

$815

ChicagoOsaka

ORD - KIX

ORDKIX

Chicago O'Hare Intl

Tue 2/24

2:35 pm-12:45 pm

1 stop31h 10m

Osaka Kansai Intl

Wed 3/4

9:25 am-12:55 pm

1 stop42h 30m

$870

ChicagoOsaka

ORD - KIX

ORDKIX

Chicago O'Hare Intl

Wed 1/21

2:35 pm-6:20 am

1 stop24h 45m

Osaka Kansai Intl

Tue 2/17

4:55 pm-12:55 pm

1 stop35h 00m

$870

ChicagoOsaka

ORD - KIX

ORDKIX

Chicago O'Hare Intl

Tue 1/20

3:35 pm-8:35 pm

2 stops38h 00m

Osaka Kansai Intl

Tue 1/27

10:50 am-8:10 pm

2 stops24h 20m

$893

ChicagoOsaka

ORD - ITM

ORDITM

Chicago O'Hare Intl

Tue 2/24

8:00 am-7:10 pm

2 stops20h 10m

Osaka Itami

Wed 3/4

4:00 pm-7:45 pm

2 stops18h 45m

$895

ChicagoOsaka

ORD - KIX

ORDKIX

Chicago O'Hare Intl

Tue 1/20

2:35 pm-6:20 am

1 stop24h 45m

Osaka Kansai Intl

Tue 2/17

4:15 pm-12:55 pm

2 stops35h 40m

$905

ChicagoOsaka

ORD - KIX

ORDKIX

Chicago O'Hare Intl

Sun 2/1

2:35 pm-2:55 pm

2 stops33h 20m

Osaka Kansai Intl

Sun 2/8

6:05 pm-12:55 pm

1 stop33h 50m

$936

ChicagoOsaka

ORD - ITM

ORDITM

Chicago O'Hare Intl

Mon 2/23

8:00 am-8:05 pm

2 stops21h 05m

Osaka Itami

Sun 3/8

4:00 pm-9:04 pm

2 stops20h 04m

$938

ChicagoOsaka

ORD - ITM

ORDITM

Chicago O'Hare Intl

Mon 1/19

8:00 am-7:10 pm

2 stops20h 10m

Osaka Itami

Mon 1/26

4:00 pm-7:45 pm

2 stops18h 45m

$938

ChicagoOsaka

ORD - ITM

ORDITM

Chicago O'Hare Intl

Tue 1/20

8:00 am-7:10 pm

2 stops20h 10m

Osaka Itami

Tue 1/27

4:00 pm-7:45 pm

2 stops18h 45m

$940

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/6

Showing 1-10 of 50 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 December.
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
OvagoPrice Accuracy2 starsTrust Score*2 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 December 5, 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 January is currently the most expensive (average of $2,112). 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 December 8, 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?

How often are flights from Chicago to Osaka delayed?

About 27% 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 26% 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 December 8, 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
1,294 reviews

Crew

8.6

Boarding

8.4

Entertainment

8.0

Food

8.1

Comfort

8.3

Overall

8.4

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
1,294 reviews
EVA Air
8.4
Very good
1,294 reviews

Crew

8.6

Boarding

8.4

Entertainment

8.0

Food

8.1

Comfort

8.3

Overall

8.4

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
1,020 reviews
EVA Air
8.4
Very good
1,294 reviews

Crew

8.6

Boarding

8.4

Entertainment

8.0

Food

8.1

Comfort

8.3

Overall

8.4

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
1,643 reviews
EVA Air
8.4
Very good
1,294 reviews

Crew

8.6

Boarding

8.4

Entertainment

8.0

Food

8.1

Comfort

8.3

Overall

8.4

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
1,088 reviews
EVA Air
8.4
Very good
1,294 reviews

Crew

8.6

Boarding

8.4

Entertainment

8.0

Food

8.1

Comfort

8.3

Overall

8.4

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
10,512 reviews
EVA Air
8.4
Very good
1,294 reviews

Crew

8.6

Boarding

8.4

Entertainment

8.0

Food

8.1

Comfort

8.3

Overall

8.4

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 20h 10m. Your travel time can differ by up to 4h 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 25% 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 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, 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 January is currently the most expensive (average of $2,112). 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 Osaka 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 December 8, 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$1,025Average$1,391FlexibilityNo cancel feeOn-time67%
EVA AirCheapest$1,097Average$1,293FlexibilityNo cancel feeOn-time74%
ANACheapest$1,173Average$1,700FlexibilityNo cancel feeOn-time80%
United AirlinesCheapest$1,570Average$1,996FlexibilityNo cancel feeOn-time69%

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