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$589+ 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 9/15. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — OSA
Aug 18 — Aug 251
Mon 8/18
Mon 8/25
1 adult, Economy
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Cheap 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 August 13, 2025.

Round-trip from

$1,135
(Delta)

One-way from

$589
(Kiwi.com)

Popular in

August

Cheapest in

October

Average price

$1,948
From Chicago Midway to Osaka (OSA)
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One-way flight from Chicago Midway to Osaka (OSA)
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Highest demand for flights based on searches. 2% potential increase in price ($42 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($48 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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Find 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 August 13, 2025.

This Delta deal was found by Cheapflights users on 8/11. 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 9/156:30 pmMDW - KIX
2 stops36h 30mDelta
Wed 9/246:10 pmKIX - MDW
2 stops38h 25mDelta
Deal found 8/11$1,135
This Delta deal was found by Cheapflights users on 8/12. 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.
Tue 8/264:25 pmMDW - KIX
2 stops34h 30mDelta
Tue 9/96:10 pmKIX - MDW
2 stops38h 27mDelta
Deal found 8/12$1,295
This Delta deal was found by Cheapflights users on 8/11. 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 9/156:30 pmMDW - KIX
2 stops32h 25mDelta
Tue 9/309:05 amKIX - MDW
2 stops37h 48mDelta
Deal found 8/11$1,383
This Delta deal was found by Cheapflights users on 8/12. 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 9/266:46 pmMDW - KIX
2 stops32h 19mDelta
Fri 10/36:20 pmKIX - MDW
2 stops32h 08mDelta
Deal found 8/12$1,395
This Delta deal was found by Cheapflights users on 8/12. 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 9/2711:00 amMDW - KIX
2 stops34h 20mDelta
Sat 10/412:35 pmKIX - MDW
2 stops34h 18mDelta
Deal found 8/12$1,400
This Delta deal was found by Cheapflights users on 8/12. 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 9/226:30 pmMDW - KIX
2 stops32h 25mDelta
Tue 9/306:10 pmKIX - MDW
2 stops41h 26mDelta
Deal found 8/12$1,458
This Delta deal was found by Cheapflights users on 8/12. 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.
Tue 9/239:35 amMDW - KIX
2 stops21h 25mDelta
Tue 9/3012:35 pmKIX - MDW
2 stops38h 28mDelta
Deal found 8/12$1,463
This Delta deal was found by Cheapflights users on 8/11. 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 9/256:30 pmMDW - KIX
2 stops36h 30mDelta
Thu 10/212:35 pmKIX - MDW
2 stops34h 18mDelta
Deal found 8/11$1,513
This Delta deal was found by Cheapflights users on 8/11. 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 10/139:35 amMDW - KIX
2 stops35h 45mDelta
Wed 10/226:10 pmKIX - MDW
2 stops32h 18mDelta
Deal found 8/11$1,546
This Delta deal was found by Cheapflights users on 8/12. 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 11/210:40 amMDW - KIX
2 stops43h 20mDelta
Sat 11/82:00 pmKIX - MDW
2 stops37h 32mDelta
Deal found 8/12$1,593
This Delta deal was found by Cheapflights users on 8/12. 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.
Wed 9/249:20 amMDW - KIX
2 stops21h 40mDelta
Thu 10/212:35 pmKIX - MDW
2 stops23h 01mDelta
Deal found 8/12$1,626
This Delta deal was found by Cheapflights users on 8/11. 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 11/206:00 amMDW - KIX
2 stops24h 00mDelta
Thu 11/272:00 pmKIX - MDW
2 stops22h 44mDelta
Deal found 8/11$1,676

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 August 13, 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 9/15

6:30 pm-9:00 pm

2 stops36h 30m

Osaka Kansai Intl

Wed 9/24

6:10 pm-6:35 pm

2 stops38h 25m

$1,135

ChicagoOsaka

MDW - KIX

MDWKIX

Chicago Midway

Tue 10/28

9:35 am-9:00 pm

2 stops21h 25m

Osaka Kansai Intl

Tue 11/4

11:55 am-10:14 pm

2 stops25h 19m

$1,295

ChicagoOsaka

MDW - KIX

MDWKIX

Chicago Midway

Tue 8/26

4:25 pm-4:55 pm

2 stops34h 30m

Osaka Kansai Intl

Tue 9/9

6:10 pm-6:37 pm

2 stops38h 27m

$1,295

ChicagoOsaka

MDW - KIX

MDWKIX

Chicago Midway

Wed 9/3

9:30 am-9:00 pm

2 stops21h 30m

Osaka Kansai Intl

Tue 9/9

6:10 pm-6:37 pm

2 stops38h 27m

$1,295

ChicagoOsaka

MDW - KIX

MDWKIX

Chicago Midway

Thu 9/11

9:35 am-11:20 am

2 stops35h 45m

Osaka Kansai Intl

Thu 9/18

12:35 pm-9:36 pm

2 stops23h 01m

$1,345

ChicagoOsaka

MDW - KIX

MDWKIX

Chicago Midway

Mon 9/15

6:30 pm-4:55 pm

2 stops32h 25m

Osaka Kansai Intl

Tue 9/30

12:35 pm-8:53 am

2 stops34h 18m

$1,383

ChicagoOsaka

MDW - KIX

MDWKIX

Chicago Midway

Fri 9/26

6:46 pm-5:05 pm

2 stops32h 19m

Osaka Kansai Intl

Fri 10/3

6:20 pm-12:28 pm

2 stops32h 08m

$1,395

ChicagoOsaka

MDW - KIX

MDWKIX

Chicago Midway

Sat 9/27

11:00 am-11:20 am

2 stops34h 20m

Osaka Kansai Intl

Sat 10/4

12:35 pm-8:53 am

2 stops34h 18m

$1,400

ChicagoOsaka

MDW - KIX

MDWKIX

Chicago Midway

Mon 9/22

10:35 am-4:55 pm

2 stops40h 20m

Osaka Kansai Intl

Tue 9/30

6:10 pm-9:36 pm

2 stops41h 26m

$1,458

ChicagoOsaka

MDW - KIX

MDWKIX

Chicago Midway

Wed 9/24

6:30 pm-5:05 pm

2 stops32h 35m

$652

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/12

Showing 1-10 of 19 results
1
2

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.

  • 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.

  • What is the cheapest month to book a flight from Chicago Midway Airport to Osaka?

    Currently, February is the cheapest month in which you can book a flight from Chicago Midway Airport to Osaka (average of $873). Flying from Chicago Midway Airport to Osaka in June is currently the most expensive (average of $1,313). 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 Midway to Osaka

See prices for flight routes from nearby airports that may be better suited for you.
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