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$479+ Cheap flights from Midway (MDW) 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 3/12. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — OSA
Jan 27 — Feb 31
Tue 1/27
Tue 2/3
1 adult, Economy
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Cheap flight deals from Midway to Osaka

Best flights from Midway to Osaka
Discover carefully curated flight deals from Midway to Osaka that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated December 28, 2025.

This Delta deal was found by Cheapflights users on 12/26. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/209:27 amMDW - KIX
2 stops21h 33mDelta
Tue 5/129:05 amKIX - MDW
2 stops26h 40mDelta
Deal found 12/26$1,138
This China Airlines deal was found by Cheapflights users on 12/25. 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 China Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/94:40 pmMDW - KIX
2 stops27h 55mMultiple Airlines
Mon 2/167:00 pmKIX - MDW
2 stops32h 30mMultiple Airlines
Deal found 12/25$1,452
This Delta deal was found by Cheapflights users on 12/25. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/226:00 amMDW - KIX
2 stops23h 45mDelta
Wed 2/49:00 amKIX - MDW
2 stops28h 22mDelta
Deal found 12/25$1,220
This Delta deal was found by Cheapflights users on 12/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/84:30 pmMDW - KIX
2 stops37h 15mDelta
Sun 2/159:00 amKIX - MDW
2 stops28h 31mDelta
Deal found 12/27$1,238
This Delta deal was found by Cheapflights users on 12/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 1/266:14 pmMDW - KIX
2 stops35h 31mDelta
Mon 2/29:00 amKIX - MDW
2 stops28h 22mDelta
Deal found 12/28$1,270
This Delta deal was found by Cheapflights users on 12/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/75:00 pmMDW - KIX
2 stops36h 45mDelta
Wed 2/2511:55 amKIX - MDW
2 stops25h 36mDelta
Deal found 12/28$1,440
This Delta deal was found by Cheapflights users on 12/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/244:30 pmMDW - KIX
2 stops37h 15mDelta
Sat 1/319:00 amKIX - MDW
2 stops28h 22mDelta
Deal found 12/27$1,457

Find flight deals from Midway to Osaka

Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) 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 28, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$1,138
(Delta)

One-way from

$479
(Kiwi.com)

Popular in

December

Cheapest in

May

Average price

$1,926
Provider with most accurate pricing for Chicago Midway-Osaka (OSA) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago Midway-Osaka (OSA) flights.
Search Deals
From Chicago Midway to Osaka (OSA)
Search Deals
One-way flight from Chicago Midway to Osaka (OSA)
Search Deals
Highest demand for flights based on searches. 9% potential increase in price ($138 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($51 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 Midway 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 28, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Osaka that are best for you.

Fly from

Midway

Fly to

Osaka

Route

Depart

Return

Price

ChicagoOsaka

MDW - KIX

MDWKIX

Chicago Midway

Mon 4/20

9:27 am-9:00 pm

2 stops21h 33m

Osaka Kansai Intl

Tue 5/12

9:05 am-9:45 pm

2 stops26h 40m

$1,138

ChicagoOsaka

MDW - KIX

MDWKIX

Chicago Midway

Thu 1/22

6:00 am-8:45 pm

2 stops23h 45m

Osaka Kansai Intl

Wed 2/4

9:00 am-10:22 pm

2 stops28h 22m

$1,220

ChicagoOsaka

MDW - KIX

MDWKIX

Chicago Midway

Sun 2/8

4:30 pm-8:45 pm

2 stops37h 15m

Osaka Kansai Intl

Sun 2/15

9:00 am-10:31 pm

2 stops28h 31m

$1,238

ChicagoOsaka

MDW - KIX

MDWKIX

Chicago Midway

Mon 1/26

6:14 pm-8:45 pm

2 stops35h 31m

Osaka Kansai Intl

Mon 2/2

9:00 am-10:22 pm

2 stops28h 22m

$1,270

ChicagoOsaka

MDW - KIX

MDWKIX

Chicago Midway

Sat 2/7

5:00 pm-8:45 pm

2 stops36h 45m

Osaka Kansai Intl

Wed 2/25

11:55 am-10:31 pm

2 stops25h 36m

$1,440

ChicagoOsaka

MDW - KIX

MDWKIX

Chicago Midway

Mon 2/9

4:40 pm-11:35 am

2 stops27h 55m

Osaka Kansai Intl

Mon 2/16

7:00 pm-12:30 pm

2 stops32h 30m

$1,452

ChicagoOsaka

MDW - KIX

MDWKIX

Chicago Midway

Sat 1/24

4:30 pm-8:45 pm

2 stops37h 15m

Osaka Kansai Intl

Sat 1/31

9:00 am-10:22 pm

2 stops28h 22m

$1,457

ChicagoOsaka

MDW - KIX

MDWKIX

Chicago Midway

Thu 3/12

7:30 am-1:00 pm

2 stops39h 30m

$479

ChicagoOsaka

MDW - KIX

MDWKIX

Chicago Midway

Sat 5/30

5:59 pm-9:00 pm

2 stops37h 01m

$1,143

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/26

Compare providers for flights from Midway 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 Midway to Osaka in December.
ProviderPrice AccuracyTrust Score*
eDreamsPrice Accuracy3 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star

*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 Midway Airport-Osaka flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Chicago Midway Airport-Osaka flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Chicago Midway Airport-Osaka flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago Midway Airport-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 Midway Airport-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 Midway to Osaka

Have a flexible travel schedule? Discover the best time to fly to Osaka from Midway 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 Midway Airport to Osaka
No data available for this route at this time. Please check back soon.

Related info for your journey

Find useful and relevant information for your journey from Midway 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 Midway Airport to Osaka?

    For as low as $1,138, Delta can have you in Osaka from Chicago Midway Airport in 21h 33m. The distance from Chicago Midway Airport to Osaka is about 6504 mi.

  • Can I find deals for flights from Midway to Osaka that include hotel bookings?

    Yes. In addition to deals on Midway to Osaka flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Midway to Osaka?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Midway to Osaka.

  • Can I find deals for business class flights from Midway to Osaka?

    Yes. Cheapflights offers flight deals from Midway 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.

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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