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Cheap flights from Chicago Midway Airport to Osaka from $370

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago Midway Airport to Osaka departing on 3/8. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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0 bags

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Find the cheapest flights from Chicago Midway Airport to Osaka

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
6:00 am - 9:00 pm
MDW
-
KIX
25h 00m
2 stops
Delta Logo
12:35 pm - 12:42 pm
KIX
-
MDW
38h 07m
2 stops
$1,136Delta
Mon, Apr 20 - Tue, May 12
Delta Logo
9:27 am - 9:00 pm
MDW
-
KIX
21h 33m
2 stops
Delta Logo
9:05 am - 9:09 pm
KIX
-
MDW
26h 04m
2 stops
$1,186Delta
Mon, Apr 20 - Tue, May 12
Delta Logo
6:38 pm - 9:00 pm
MDW
-
KIX
36h 22m
2 stops
Delta Logo
12:35 pm - 12:42 pm
KIX
-
MDW
38h 07m
2 stops
$1,283Delta
Thu, Apr 23 - Fri, May 8
Delta Logo
7:20 pm - 9:00 pm
MDW
-
KIX
35h 40m
2 stops
Delta Logo
9:05 am - 10:28 pm
KIX
-
MDW
27h 23m
2 stops
$1,374Delta
Mon, Apr 6 - Wed, Apr 22
Multiple Airlines Logo
8:35 pm - 12:00 pm
MDW
-
KIX
25h 25m
2 stops
Multiple Airlines Logo
2:00 pm - 5:05 am
KIX
-
MDW
29h 05m
2 stops
$1,488Multiple Airlines
Sat, Aug 1 - Mon, Aug 10
Multiple Airlines Logo
8:35 pm - 12:00 pm
MDW
-
KIX
25h 25m
2 stops
Multiple Airlines Logo
2:00 pm - 5:05 am
KIX
-
MDW
29h 05m
2 stops
$1,576Multiple Airlines
Sat, Aug 1 - Mon, Aug 10
Multiple Airlines Logo
10:55 am - 11:35 am
MDW
-
KIX
34h 40m
2 stops
Multiple Airlines Logo
7:05 pm - 5:30 am
KIX
-
MDW
24h 25m
2 stops
$1,577Multiple Airlines
Wed, Mar 25 - Wed, Apr 1
Delta Logo
7:20 pm - 9:00 pm
MDW
-
KIX
35h 40m
2 stops
Delta Logo
12:35 pm - 10:28 pm
KIX
-
MDW
23h 53m
2 stops
$1,581Delta
Mon, Apr 6 - Wed, Apr 22
Delta Logo
9:23 am - 9:00 pm
MDW
-
KIX
21h 37m
2 stops
Delta Logo
9:05 am - 9:09 pm
KIX
-
MDW
26h 04m
2 stops
$1,600Delta
Thu, May 7 - Thu, May 21
Delta Logo
7:16 pm - 9:00 pm
MDW
-
KIX
35h 44m
2 stops
Delta Logo
12:35 pm - 12:42 pm
KIX
-
MDW
38h 07m
2 stops
$1,606Delta
Wed, May 6 - Wed, May 20

Delta flights from Chicago Midway Airport to Osaka

Our best Delta deals on Chicago Midway Airport to Osaka flight tickets
Delta
Apr 20
MDW9:31 amChicago Midway
21h 29m
2 stops
KIX9:00 pmOsaka Kansai Intl
May 12
KIX9:05 amOsaka Kansai Intl
26h 04m
2 stops
MDW9:09 pmChicago Midway
$1,136
Delta
Apr 20
MDW9:27 amChicago Midway
21h 33m
2 stops
KIX9:00 pmOsaka Kansai Intl
May 12
KIX9:05 amOsaka Kansai Intl
26h 04m
2 stops
MDW9:09 pmChicago Midway
$1,186
Delta
Apr 23
MDW6:38 pmChicago Midway
36h 22m
2 stops
KIX9:00 pmOsaka Kansai Intl
May 8
KIX12:35 pmOsaka Kansai Intl
38h 07m
2 stops
MDW12:42 pmChicago Midway
$1,283

Air France flights from Chicago Midway Airport to Osaka

Our best Air France deals on Chicago Midway Airport to Osaka flight tickets
Air France
Apr 6
MDW6:34 pmChicago Midway
25h 06m
2 stops
KIX9:40 amOsaka Kansai Intl
Apr 22
KIX11:25 amOsaka Kansai Intl
43h 00m
2 stops
MDW4:25 pmChicago Midway
$1,945
Air France
Mar 4
MDW12:45 pmChicago Midway
31h 05m
2 stops
KIX10:50 amOsaka Kansai Intl
Mar 16
KIX12:45 pmOsaka Kansai Intl
43h 09m
2 stops
MDW5:54 pmChicago Midway
$2,091
Air France
Apr 7
MDW6:34 pmChicago Midway
25h 06m
2 stops
KIX9:40 amOsaka Kansai Intl
Apr 20
KIX11:25 amOsaka Kansai Intl
43h 00m
2 stops
MDW4:25 pmChicago Midway
$2,112

momondo Fare Finder

 
Customize your flight search to find flights from Chicago Midway Airport 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, momondo users made 832,500 searches. Data last updated February 11, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Osaka that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoOsaka

MDW - KIX

MDWKIX

Chicago Midway

Mon 4/20

6:00 am-9:00 pm

2 stops25h 00m

Osaka Kansai Intl

Tue 5/12

12:35 pm-12:42 pm

2 stops38h 07m

$1,136

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-9:09 pm

2 stops26h 04m

$1,186

ChicagoOsaka

MDW - KIX

MDWKIX

Chicago Midway

Thu 4/23

6:38 pm-9:00 pm

2 stops36h 22m

Osaka Kansai Intl

Fri 5/8

12:35 pm-12:42 pm

2 stops38h 07m

$1,283

ChicagoOsaka

MDW - KIX

MDWKIX

Chicago Midway

Mon 4/6

7:20 pm-9:00 pm

2 stops35h 40m

Osaka Kansai Intl

Wed 4/22

9:05 am-10:28 pm

2 stops27h 23m

$1,374

ChicagoOsaka

MDW - KIX

MDWKIX

Chicago Midway

Sat 8/1

8:35 pm-12:00 pm

2 stops25h 25m

Osaka Kansai Intl

Mon 8/10

2:00 pm-5:05 am

2 stops29h 05m

$1,488

ChicagoOsaka

MDW - KIX

MDWKIX

Chicago Midway

Sat 8/1

8:35 pm-12:00 pm

2 stops25h 25m

Osaka Kansai Intl

Mon 8/10

2:00 pm-5:05 am

2 stops29h 05m

$1,576

ChicagoOsaka

MDW - KIX

MDWKIX

Chicago Midway

Wed 3/25

10:55 am-11:35 am

2 stops34h 40m

Osaka Kansai Intl

Wed 4/1

7:05 pm-5:30 am

2 stops24h 25m

$1,577

ChicagoOsaka

MDW - KIX

MDWKIX

Chicago Midway

Mon 4/6

7:20 pm-9:00 pm

2 stops35h 40m

Osaka Kansai Intl

Wed 4/22

12:35 pm-10:28 pm

2 stops23h 53m

$1,581

ChicagoOsaka

MDW - KIX

MDWKIX

Chicago Midway

Thu 5/7

9:23 am-9:00 pm

2 stops21h 37m

Osaka Kansai Intl

Thu 5/21

9:05 am-9:09 pm

2 stops26h 04m

$1,600

ChicagoOsaka

MDW - KIX

MDWKIX

Chicago Midway

Wed 5/6

7:16 pm-9:00 pm

2 stops35h 44m

Osaka Kansai Intl

Wed 5/20

12:35 pm-12:42 pm

2 stops38h 07m

$1,606

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

When to book flights from Chicago Midway Airport to Osaka

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago Midway Airport to Osaka according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Chicago Midway Airport to Osaka (MDW to OSA) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to Osaka

Fastest flight time

24h 45m

Direct flights

None
The fastest flight from Chicago Midway Airport to Osaka takes 24h 45m
There are no direct flights from Chicago Midway Airport to Osaka. There are no popular flight routes from Chicago Midway Airport to Osaka.
Search flight deals

  • How far is Chicago Midway to Osaka by plane?

    Chicago Midway and Osaka are 6481.8 mi apart from one another. In terms of flight time, this usually takes a little over 24h 45m.

  • When did momondo last update prices for flights from Chicago Midway Airport to Osaka?

    Prices for flights from Chicago Midway Airport to Osaka are refreshed on a daily basis.

  • How old do you have to be to fly from Chicago Midway Airport to Osaka?

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago Midway Airport to Osaka.

  • What documentation or ID do you need to fly to Osaka?

    The necessary travel and health documents for your Osaka trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

  • How do I get Price Alerts for flights from Chicago Midway Airport to Osaka?

    Confirm your travel details to search for the latest offers for flights from Chicago Midway Airport to Osaka. While browsing offers there will be the option to toggle “Price Alerts”. You’ll then receive updates when prices for the flight route increase or decrease.

  • How can I save money on flights from Chicago Midway Airport to Osaka with momondo?

    Leverage our AI within our “Price Forecast” tool, which predicts if it’s better to book now or wait until prices decrease. You can strategically pick the best days to fly and save money on your trip by using our “Price Calendar” tool. “Explore” shows an overview of how much it costs to fly to anywhere from a selected city or airport. Our “Discover” content is a great option for travel inspiration and money-saving tips, while “Price Alerts” will update you when prices change, so you can book when fares are right.

  • How does momondo find its flight prices?

    We aggregate our prices from over 700+ competitors from airlines to OTAs. We operate in over 30 markets worldwide to show you a wide range of travel options.

Traveling to a place near Osaka?

Book flights to Osaka if you plan to visit one of these locations
Nara
Nishinomiya

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Osaka?

It is quick and easy to find Chicago to Osaka flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Osaka that suits you.

Can I find flights from Chicago to Osaka with flexible booking policies on momondo?

Flights from Chicago to Osaka with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

How can momondo help me find flights from Chicago to Osaka?

Once all potential Chicago to Osaka flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

I’m not ready to book a flight from Chicago to Osaka right now. Can momondo alert me if prices change?

If you are not ready to book a flight from Chicago to Osaka now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Osaka and let you know when they change.

An easier way to manage your Osaka trip

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Find better results for your trip to Japan

Fly into one of these airports located in Osaka

Airports listed have a maximum distance of 22.5 mi from Osaka
Osaka Itami Airport
Osaka Kansai Intl Airport