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$476+ 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 2/15. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — OSA
Feb 21 — Feb 281
Sat 2/21
Sat 2/28
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 January 22, 2026.

This Delta deal was found by Cheapflights users on 1/20. 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 4/209:26 am
MDW
-
KIX
2 stops21h 34m
Delta
Tue 5/129:05 am
KIX
-
MDW
2 stops26h 40m
Delta
Deal found 1/20$1,113
This China Airlines deal was found by Cheapflights users on 1/21. 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.
Wed 8/268:45 pm
MDW
-
KIX
2 stops25h 15m
Multiple Airlines
Wed 9/22:00 pm
KIX
-
MDW
2 stops22h 55m
Multiple Airlines
Deal found 1/21$1,251
This Delta deal was found by Cheapflights users on 1/21. 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 10/46:00 am
MDW
-
KIX
2 stops25h 00m
Delta
Sat 10/176:20 pm
KIX
-
MDW
2 stops36h 05m
Delta
Deal found 1/21$1,293
This China Airlines deal was found by Cheapflights users on 1/21. 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.
Sun 8/238:35 pm
MDW
-
KIX
2 stops25h 25m
Multiple Airlines
Sun 8/302:00 pm
KIX
-
MDW
2 stops24h 25m
Multiple Airlines
Deal found 1/21$1,295
This Delta deal was found by Cheapflights users on 1/20. 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 3/312:45 pm
MDW
-
KIX
2 stops31h 00m
Delta
Tue 3/1011:55 am
KIX
-
MDW
2 stops24h 36m
Delta
Deal found 1/20$1,320
This China Airlines deal was found by Cheapflights users on 1/20. 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.
Sat 8/18:35 pm
MDW
-
KIX
2 stops25h 25m
Multiple Airlines
Mon 8/107:05 pm
KIX
-
MDW
2 stops24h 45m
Multiple Airlines
Deal found 1/20$1,351
This China Airlines deal was found by Cheapflights users on 1/21. 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.
Fri 3/135:40 pm
MDW
-
KIX
2 stops27h 55m
Multiple Airlines
Sun 3/227:00 pm
KIX
-
MDW
2 stops24h 55m
Multiple Airlines
Deal found 1/21$1,420
This China Airlines deal was found by Cheapflights users on 1/20. 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.
Wed 3/2510:55 am
MDW
-
KIX
2 stops34h 40m
Multiple Airlines
Wed 4/17:05 pm
KIX
-
MDW
2 stops24h 25m
Multiple Airlines
Deal found 1/20$1,437
This Delta deal was found by Cheapflights users on 1/19. 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 11/71:05 pm
MDW
-
KIX
2 stops30h 40m
Delta
Sun 11/159:00 am
KIX
-
MDW
2 stops27h 45m
Delta
Deal found 1/19$1,557
This China Airlines deal was found by Cheapflights users on 1/21. 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.
Sat 3/76:20 pm
MDW
-
KIX
2 stops26h 15m
Multiple Airlines
Sat 3/142:30 pm
KIX
-
MDW
2 stops29h 00m
Multiple Airlines
Deal found 1/21$1,632
This Delta deal was found by Cheapflights users on 1/20. 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 5/269:20 am
MDW
-
KIX
2 stops36h 00m
Delta
Wed 6/39:05 am
KIX
-
MDW
2 stops26h 40m
Delta
Deal found 1/20$1,652

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 January 22, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
1 star

Round-trip from

$1,113
(Delta)

One-way from

$476
(Kiwi.com)

Popular in

December

Cheapest in

May

Average price

$1,183
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. 15% potential increase in price ($248 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 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 January 22, 2026.
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

Tue 3/3

12:45 pm-10:45 am

2 stops31h 00m

Osaka Kansai Intl

Tue 3/10

11:55 am-10:31 pm

2 stops24h 36m

$1,320

ChicagoOsaka

MDW - KIX

MDWKIX

Chicago Midway

Fri 3/13

5:40 pm-11:35 am

2 stops27h 55m

Osaka Kansai Intl

Sun 3/22

7:00 pm-5:55 am

2 stops24h 55m

$1,420

ChicagoOsaka

MDW - KIX

MDWKIX

Chicago Midway

Tue 5/26

9:20 am-11:20 am

2 stops36h 00m

Osaka Kansai Intl

Wed 6/3

9:05 am-9:45 pm

2 stops26h 40m

$1,652

ChicagoOsaka

MDW - KIX

MDWKIX

Chicago Midway

Wed 2/11

2:10 pm-11:35 am

2 stops30h 25m

Osaka Kansai Intl

Wed 2/25

7:00 pm-4:55 am

2 stops24h 55m

$1,667

ChicagoOsaka

MDW - KIX

MDWKIX

Chicago Midway

Tue 3/3

10:49 am-10:45 am

2 stops32h 56m

Osaka Kansai Intl

Sat 3/7

6:10 pm-11:29 am

2 stops32h 19m

$1,668

ChicagoOsaka

MDW - KIX

MDWKIX

Chicago Midway

Sun 5/17

6:00 am-9:00 pm

2 stops25h 00m

Osaka Kansai Intl

Fri 5/29

9:05 am-9:45 pm

2 stops26h 40m

$1,672

ChicagoOsaka

MDW - KIX

MDWKIX

Chicago Midway

Mon 2/9

1:51 pm-10:50 am

2 stops29h 59m

Osaka Kansai Intl

Mon 2/23

12:45 pm-5:45 pm

2 stops44h 00m

$1,773

ChicagoOsaka

MDW - KIX

MDWKIX

Chicago Midway

Tue 2/17

6:40 pm-11:20 am

2 stops25h 40m

Osaka Kansai Intl

Tue 2/24

1:00 pm-5:37 pm

2 stops43h 37m

$1,773

ChicagoOsaka

MDW - KIX

MDWKIX

Chicago Midway

Fri 5/15

7:40 pm-12:00 pm

2 stops26h 20m

Osaka Kansai Intl

Sun 5/24

7:05 pm-5:20 am

2 stops24h 15m

$1,776

ChicagoOsaka

MDW - KIX

MDWKIX

Chicago Midway

Tue 2/10

6:14 pm-11:20 am

2 stops26h 06m

Osaka Kansai Intl

Mon 2/23

12:45 pm-5:45 pm

2 stops44h 00m

$1,779

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/21

Showing 1-10 of 23 results
1
2
3
  • Most accurate provider: When it comes to deals on Chicago Midway Airport-Osaka flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago Midway Airport-Osaka flight deals on Cheapflights vs. FlightHub >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 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 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 $1,320, Delta can have you in Osaka from Chicago Midway Airport in 31h. 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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