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$764+ 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 5/17. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — OSA
Jan 3 — Jan 101
Sat 1/3
Sat 1/10
1 adult, Economy
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Cheap flight deals from Midway to Osaka

Cheapest flights from Midway to Osaka
Explore the most affordable flight options available from Midway to Osaka. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 4, 2025.

This KLM deal was found by Cheapflights users on 12/3. 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 KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/75:13 pmMDW - KIX
2 stops27h 07mKLM
Sun 12/211:00 pmKIX - MDW
2 stops42h 20mKLM
Deal found 12/3$2,789
This Delta deal was found by Cheapflights users on 12/3. 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.
Fri 12/126:00 amMDW - KIX
2 stops23h 45mDelta
Fri 12/199:00 amKIX - MDW
2 stops29h 47mDelta
Deal found 12/3$3,047
This Delta deal was found by Cheapflights users on 12/4. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/286:00 amMDW - KIX
2 stops23h 45mDelta
Sun 1/411:55 amKIX - MDW
2 stops39h 53mDelta
Deal found 12/4$3,495
This Delta deal was found by Cheapflights users on 12/3. 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 12/86:00 amMDW - KIX
2 stops23h 45mDelta
Tue 12/1611:55 amKIX - MDW
2 stops26h 52mDelta
Deal found 12/3$10,267

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 4, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$1,223
(China Airlines)

One-way from

$764
(Delta)

Popular in

December

Cheapest in

May

Average price

$1,988
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 ($145 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($56 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 4, 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

9:20 am-9:00 pm

2 stops21h 40m

Osaka Kansai Intl

Tue 5/12

9:05 am-9:45 pm

2 stops26h 40m

$1,291

ChicagoOsaka

MDW - KIX

MDWKIX

Chicago Midway

Wed 4/29

6:50 pm-12:00 pm

2 stops27h 10m

Osaka Kansai Intl

Wed 5/13

1:10 pm-11:20 pm

2 stops24h 10m

$1,324

ChicagoOsaka

MDW - KIX

MDWKIX

Chicago Midway

Fri 4/24

7:40 pm-12:00 pm

2 stops26h 20m

Osaka Kansai Intl

Fri 5/1

2:00 pm-10:10 pm

2 stops22h 10m

$1,324

ChicagoOsaka

MDW - KIX

MDWKIX

Chicago Midway

Sat 1/17

5:31 pm-8:45 pm

2 stops36h 14m

Osaka Kansai Intl

Sat 1/24

9:00 am-10:22 pm

2 stops28h 22m

$1,457

ChicagoOsaka

MDW - KIX

MDWKIX

Chicago Midway

Sun 1/18

5:59 pm-10:45 am

2 stops25h 46m

Osaka Kansai Intl

Sun 1/25

9:00 am-10:22 pm

2 stops28h 22m

$1,507

ChicagoOsaka

MDW - KIX

MDWKIX

Chicago Midway

Thu 4/16

6:00 am-9:00 pm

2 stops25h 00m

Osaka Kansai Intl

Thu 4/23

12:35 pm-9:45 pm

2 stops23h 10m

$1,772

ChicagoOsaka

MDW - KIX

MDWKIX

Chicago Midway

Sun 4/19

5:25 pm-5:05 pm

2 stops33h 40m

Osaka Kansai Intl

Mon 4/27

12:35 pm-9:45 pm

2 stops23h 10m

$1,772

ChicagoOsaka

MDW - KIX

MDWKIX

Chicago Midway

Fri 5/15

7:40 pm-12:00 pm

2 stops26h 20m

Osaka Kansai Intl

Sun 5/24

2:00 pm-12:10 am

2 stops24h 10m

$1,880

ChicagoOsaka

MDW - KIX

MDWKIX

Chicago Midway

Mon 4/13

9:20 am-9:00 pm

2 stops21h 40m

Osaka Kansai Intl

Thu 4/16

9:05 am-9:45 pm

2 stops26h 40m

$2,124

ChicagoOsaka

MDW - KIX

MDWKIX

Chicago Midway

Sat 4/25

5:59 pm-9:00 pm

2 stops37h 01m

Osaka Kansai Intl

Thu 4/30

6:20 pm-4:25 pm

2 stops36h 05m

$2,389

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/4

Showing 1-10 of 15 results
1
2

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 $1,291, Delta can have you in Osaka from Chicago Midway Airport in 21h 40m. 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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Alternative routes for Midway to Osaka

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