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$423+ 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 12/7. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — OSA
Dec 6 — Dec 131
Sat 12/6
Sat 12/13
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 November 6, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$1,027
(Trip.com)

One-way from

$423
(Kiwi.com)

Popular in

December

Cheapest in

September

Average price

$1,372
Provider with most accurate pricing for Chicago Midway-Osaka (OSA) flight deals.
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Provider most trusted by Cheapflights users for Chicago Midway-Osaka (OSA) flights.
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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. 3% potential increase in price ($57 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($49 potential savings vs. average RT price).
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Average for round-trip flights in November 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 November 6, 2025.

This Trip.com deal was found by Cheapflights users on 11/4. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/72:01 pmMDW - KIX
2 stops37h 49mMultiple Airlines
Thu 12/185:50 pmKIX - MDW
2 stops43h 08mMultiple Airlines
Deal found 11/4$1,027
This Trip.com deal was found by Cheapflights users on 11/5. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/48:05 amMDW - KIX
2 stops43h 45mMultiple Airlines
Mon 12/155:50 pmKIX - MDW
2 stops29h 56mMultiple Airlines
Deal found 11/5$1,051
This Delta deal was found by Cheapflights users on 11/4. 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 11/306:48 pmMDW - KIX
2 stops34h 57mDelta
Thu 12/1111:55 amKIX - MDW
2 stops26h 52mDelta
Deal found 11/4$1,244
This Delta deal was found by Cheapflights users on 11/3. 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 12/16:00 amMDW - KIX
2 stops23h 45mDelta
Mon 12/811:55 amKIX - MDW
2 stops26h 52mDelta
Deal found 11/3$1,437
This Delta deal was found by Cheapflights users on 11/6. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/297:02 pmMDW - KIX
2 stops34h 43mDelta
Mon 12/159:00 amKIX - MDW
2 stops29h 47mDelta
Deal found 11/6$1,448
This Delta deal was found by Cheapflights users on 11/5. 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 12/56:00 amMDW - KIX
2 stops23h 45mDelta
Mon 12/1511:55 amKIX - MDW
2 stops26h 52mDelta
Deal found 11/5$1,457
This Delta deal was found by Cheapflights users on 11/6. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/295:59 pmMDW - KIX
2 stops35h 46mDelta
Thu 1/159:00 amKIX - MDW
2 stops28h 09mDelta
Deal found 11/6$1,476
This Delta deal was found by Cheapflights users on 11/5. 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 11/297:02 pmMDW - KIX
2 stops34h 43mDelta
Tue 12/99:00 amKIX - MDW
2 stops29h 47mDelta
Deal found 11/5$1,478
This Delta deal was found by Cheapflights users on 11/5. 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 12/56:00 amMDW - KIX
2 stops23h 45mDelta
Sat 12/1311:55 amKIX - MDW
2 stops26h 52mDelta
Deal found 11/5$1,487
This Delta deal was found by Cheapflights users on 11/5. 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 11/285:34 pmMDW - KIX
2 stops28h 16mDelta
Sun 12/149:00 amKIX - MDW
2 stops29h 47mDelta
Deal found 11/5$1,492
This Delta deal was found by Cheapflights users on 11/6. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/76:00 amMDW - KIX
2 stops23h 45mDelta
Sun 12/1411:55 amKIX - MDW
2 stops26h 52mDelta
Deal found 11/6$1,522
This Delta deal was found by Cheapflights users on 11/5. 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 11/275:34 pmMDW - KIX
2 stops36h 11mDelta
Mon 12/811:55 amKIX - MDW
2 stops26h 52mDelta
Deal found 11/5$1,557

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 November 6, 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

Sun 12/7

2:01 pm-6:50 pm

2 stops37h 49m

Osaka Kansai Intl

Thu 12/18

5:50 pm-9:58 pm

2 stops43h 08m

$1,027

ChicagoOsaka

MDW - KIX

MDWKIX

Chicago Midway

Thu 12/4

8:05 am-6:50 pm

2 stops43h 45m

Osaka Kansai Intl

Mon 12/15

5:50 pm-8:46 am

2 stops29h 56m

$1,051

ChicagoOsaka

MDW - KIX

MDWKIX

Chicago Midway

Sun 11/30

6:48 pm-8:45 pm

2 stops34h 57m

Osaka Kansai Intl

Thu 12/11

11:55 am-11:47 pm

2 stops26h 52m

$1,244

ChicagoOsaka

MDW - KIX

MDWKIX

Chicago Midway

Mon 12/1

6:00 am-8:45 pm

2 stops23h 45m

Osaka Kansai Intl

Mon 12/8

11:55 am-11:47 pm

2 stops26h 52m

$1,437

ChicagoOsaka

MDW - KIX

MDWKIX

Chicago Midway

Sat 11/29

7:02 pm-8:45 pm

2 stops34h 43m

Osaka Kansai Intl

Mon 12/15

9:00 am-11:47 pm

2 stops29h 47m

$1,448

ChicagoOsaka

MDW - KIX

MDWKIX

Chicago Midway

Fri 12/5

6:00 am-8:45 pm

2 stops23h 45m

Osaka Kansai Intl

Mon 12/15

11:55 am-11:47 pm

2 stops26h 52m

$1,457

ChicagoOsaka

MDW - KIX

MDWKIX

Chicago Midway

Mon 12/29

5:59 pm-8:45 pm

2 stops35h 46m

Osaka Kansai Intl

Thu 1/15

9:00 am-10:09 pm

2 stops28h 09m

$1,476

ChicagoOsaka

MDW - KIX

MDWKIX

Chicago Midway

Sat 11/29

7:02 pm-8:45 pm

2 stops34h 43m

Osaka Kansai Intl

Tue 12/9

9:00 am-11:47 pm

2 stops29h 47m

$1,478

ChicagoOsaka

MDW - KIX

MDWKIX

Chicago Midway

Fri 12/5

6:00 am-8:45 pm

2 stops23h 45m

Osaka Kansai Intl

Sat 12/13

11:55 am-11:47 pm

2 stops26h 52m

$1,487

ChicagoOsaka

MDW - KIX

MDWKIX

Chicago Midway

Fri 11/28

5:34 pm-12:50 pm

2 stops28h 16m

Osaka Kansai Intl

Sun 12/14

9:00 am-11:47 pm

2 stops29h 47m

$1,492

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/6

Showing 1-10 of 21 results
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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 November.
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 $1,244, Delta can have you in Osaka from Chicago Midway Airport in 34h 57m. 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
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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