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$464+ 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 2/16. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — OSA
Feb 27 — Mar 61
Fri 2/27
Fri 3/6
1 adult, Economy
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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 January 28, 2026.

This FlightHub deal was found by Cheapflights users on 1/26. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/147:40 am
ORD
-
ITM
2 stops21h 15m
ANA
Tue 4/287:05 am
ITM
-
ORD
1 stop15h 35m
ANA
Deal found 1/26$848
This FlightHub deal was found by Cheapflights users on 1/26. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/2012:15 pm
ORD
-
UKB
1 stop19h 30m
ANA
Tue 5/127:05 am
UKB
-
ORD
1 stop15h 35m
ANA
Deal found 1/26$849
This FlightHub deal was found by Cheapflights users on 1/28. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/2012:15 pm
ORD
-
ITM
1 stop15h 55m
ANA
Tue 5/127:05 am
ITM
-
ORD
1 stop15h 35m
ANA
Deal found 1/28$851
This FlightHub deal was found by Cheapflights users on 1/26. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/1411:50 am
ORD
-
KIX
1 stop18h 00m
ANA
Tue 4/286:45 am
KIX
-
ORD
1 stop15h 55m
ANA
Deal found 1/26$852
This United Airlines deal was found by Cheapflights users on 1/26. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/125:45 pm
ORD
-
ITM
1 stop33h 20m
United Airlines
Thu 4/3012:00 pm
ITM
-
ORD
1 stop34h 40m
United Airlines
Deal found 1/26$856
This United Airlines deal was found by Cheapflights users on 1/26. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/139:20 pm
ORD
-
ITM
2 stops29h 45m
United Airlines
Thu 4/3012:00 pm
ITM
-
ORD
1 stop34h 40m
United Airlines
Deal found 1/26$861
This Air Canada deal was found by Cheapflights users on 1/26. 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 4/213:40 pm
ORD
-
KIX
1 stop34h 45m
Air Canada
Thu 4/306:00 pm
KIX
-
ORD
1 stop34h 45m
Air Canada
Deal found 1/26$861
This United Airlines deal was found by Cheapflights users on 1/27. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/206:25 am
ORD
-
ITM
2 stops20h 40m
United Airlines
Tue 5/1212:00 pm
ITM
-
ORD
1 stop34h 40m
United Airlines
Deal found 1/27$862
This KAYAK deal was found by Cheapflights users on 1/28. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/206:25 am
ORD
-
KIX
1 stop18h 25m
ANA
Tue 5/126:45 am
KIX
-
ORD
1 stop22h 30m
ANA
Deal found 1/28$863
This United Airlines deal was found by Cheapflights users on 1/26. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/206:25 am
ORD
-
KIX
1 stop18h 25m
United Airlines
Tue 5/124:55 pm
KIX
-
ORD
1 stop17h 32m
United Airlines
Deal found 1/26$865
This Air Canada deal was found by Cheapflights users on 1/26. 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 4/208:20 pm
ORD
-
KIX
2 stops54h 05m
Air Canada
Tue 5/126:00 pm
KIX
-
ORD
1 stop34h 45m
Air Canada
Deal found 1/26$869
This United Airlines deal was found by Cheapflights users on 1/26. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/126:15 pm
ORD
-
KIX
2 stops30h 35m
United Airlines
Thu 4/304:55 pm
KIX
-
ORD
2 stops30h 43m
United Airlines
Deal found 1/26$870

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 January 28, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$848
(FlightHub)

One-way from

$464
(Kiwi.com)

Popular in

December

Cheapest in

May

Average price

$1,183
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. 15% potential increase in price ($250 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($54 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
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 January 28, 2026.
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

ChicagoKobe

ORD - UKB

ORDUKB

Chicago O'Hare Intl

Mon 4/20

12:15 pm-9:45 pm

1 stop19h 30m

Kobe

Tue 5/12

7:05 am-8:40 am

1 stop15h 35m

$850

ChicagoOsaka

ORD - ITM

ORDITM

Chicago O'Hare Intl

Tue 4/14

6:25 am-5:05 pm

2 stops20h 40m

Osaka Itami

Thu 4/30

12:00 pm-8:40 am

1 stop34h 40m

$861

ChicagoOsaka

ORD - ITM

ORDITM

Chicago O'Hare Intl

Mon 4/20

6:25 am-5:05 pm

2 stops20h 40m

Osaka Itami

Tue 5/12

12:00 pm-8:40 am

1 stop34h 40m

$861

ChicagoOsaka

ORD - ITM

ORDITM

Chicago O'Hare Intl

Sat 4/18

9:20 pm-5:05 pm

2 stops29h 45m

Osaka Itami

Thu 4/30

12:00 pm-8:40 am

1 stop34h 40m

$861

ChicagoOsaka

ORD - KIX

ORDKIX

Chicago O'Hare Intl

Mon 4/20

6:25 am-2:50 pm

1 stop18h 25m

Osaka Kansai Intl

Tue 5/12

4:55 pm-8:27 pm

1 stop17h 32m

$866

ChicagoOsaka

ORD - KIX

ORDKIX

Chicago O'Hare Intl

Tue 4/14

6:25 am-2:50 pm

1 stop18h 25m

Osaka Kansai Intl

Thu 4/30

4:55 pm-9:38 am

2 stops30h 43m

$870

ChicagoOsaka

ORD - ITM

ORDITM

Chicago O'Hare Intl

Tue 4/21

6:00 am-5:05 pm

2 stops21h 05m

Osaka Itami

Thu 4/30

12:00 pm-11:15 pm

2 stops49h 15m

$872

ChicagoOsaka

ORD - KIX

ORDKIX

Chicago O'Hare Intl

Wed 2/25

6:25 am-4:40 pm

1 stop19h 15m

Osaka Kansai Intl

Sat 5/23

8:30 am-5:05 am

2 stops34h 35m

$996

ChicagoOsaka

ORD - KIX

ORDKIX

Chicago O'Hare Intl

Mon 3/2

9:15 pm-4:40 pm

2 stops28h 25m

Osaka Kansai Intl

Mon 3/16

6:35 pm-12:58 am

2 stops20h 23m

$999

ChicagoOsaka

ORD - KIX

ORDKIX

Chicago O'Hare Intl

Sun 2/15

2:35 pm-5:50 pm

1 stop36h 15m

Osaka Kansai Intl

Thu 3/5

6:05 pm-12:55 pm

1 stop33h 50m

$1,030

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/27

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 January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
AranGrantPrice Accuracy2 starsTrust Score*2 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
OvagoPrice 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 FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Osaka flight deals on Cheapflights vs. FlightHub >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 FlightHub the most. FlightHub 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 January 23, 2026.

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, 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 $2,094). 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.

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

How often are flights from Chicago to Osaka delayed?

About 32% of weekly flights between Chicago and Osaka have experienced delays in the past year, with the average delay time being 143 minutes.

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

Historically, flights departing in the morning 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?

Monday 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 32% 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 January 28, 2026.
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
1,334 reviews

Food

8.1

Boarding

8.4

Comfort

8.3

Entertainment

8.0

Crew

8.6

Overall

8.4

Reviews

1 / 20
6.0
Good

Hannah,Jan 2026

SFO - TPE

It's alright. I wish I was assigned a seat on the isle side. I was not able to pick a seat during booking. So, I was seated in between two guys. For a 14 hours flight, it was barely bearable.
EVA Air
8.4
Very good
1,334 reviews
EVA Air
8.4
Very good
1,334 reviews

Food

8.1

Boarding

8.4

Comfort

8.3

Entertainment

8.0

Crew

8.6

Overall

8.4

Reviews

1 / 20
6.0
Good

Hannah,Jan 2026

SFO - TPE

It's alright. I wish I was assigned a seat on the isle side. I was not able to pick a seat during booking. So, I was seated in between two guys. For a 14 hours flight, it was barely bearable.
ANA
8.4
Very good
1,078 reviews
EVA Air
8.4
Very good
1,334 reviews

Food

8.1

Boarding

8.4

Comfort

8.3

Entertainment

8.0

Crew

8.6

Overall

8.4

Reviews

1 / 20
6.0
Good

Hannah,Jan 2026

SFO - TPE

It's alright. I wish I was assigned a seat on the isle side. I was not able to pick a seat during booking. So, I was seated in between two guys. For a 14 hours flight, it was barely bearable.
Japan Airlines
8.3
Very good
1,691 reviews
EVA Air
8.4
Very good
1,334 reviews

Food

8.1

Boarding

8.4

Comfort

8.3

Entertainment

8.0

Crew

8.6

Overall

8.4

Reviews

1 / 20
6.0
Good

Hannah,Jan 2026

SFO - TPE

It's alright. I wish I was assigned a seat on the isle side. I was not able to pick a seat during booking. So, I was seated in between two guys. For a 14 hours flight, it was barely bearable.
Cathay Pacific
7.6
Good
1,148 reviews
EVA Air
8.4
Very good
1,334 reviews

Food

8.1

Boarding

8.4

Comfort

8.3

Entertainment

8.0

Crew

8.6

Overall

8.4

Reviews

1 / 20
6.0
Good

Hannah,Jan 2026

SFO - TPE

It's alright. I wish I was assigned a seat on the isle side. I was not able to pick a seat during booking. So, I was seated in between two guys. For a 14 hours flight, it was barely bearable.
Air Canada
7.1
Good
10,666 reviews
EVA Air
8.4
Very good
1,334 reviews

Food

8.1

Boarding

8.4

Comfort

8.3

Entertainment

8.0

Crew

8.6

Overall

8.4

Reviews

1 / 20
6.0
Good

Hannah,Jan 2026

SFO - TPE

It's alright. I wish I was assigned a seat on the isle side. I was not able to pick a seat during booking. So, I was seated in between two guys. For a 14 hours flight, it was barely bearable.

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?

    ANA, United Airlines, and EVA Air can get you from Chicago to Osaka in just under 19h 30m. Your travel time can differ by up to 1h 10m. 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 EVA Air. Our recent data shows that you can find tickets from as low as $1,008 on this airline. Additional options worth looking into are ANA and Air Canada, starting at $1,022 and $1,025 round-trip. You may be able to fly from Chicago to Osaka for 24% 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 - Kobe or Chicago O'Hare Intl - Osaka Itami.

  • 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 $2,094). 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 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 January 28, 2026.
AirlineCheapestAverageFlexibilityOn-time
EVA AirCheapest$1,008Average$1,167FlexibilityNo cancel feeOn-time74%
ANACheapest$1,022Average$1,635FlexibilityNo cancel feeOn-time80%
Air CanadaCheapest$1,025Average$1,391FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$1,570Average$1,698FlexibilityNo cancel feeOn-time69%

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