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Cheap flights from Chicago Midway Airport to Osaka from $471

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 9/11. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

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
5:10 pm - 8:45 pm
MDW
-
KIX
37h 35m
2 stops
Delta Logo
12:35 pm - 10:36 pm
KIX
-
MDW
24h 01m
2 stops
$1,214Delta
Sun, Aug 30 - Sun, Sep 6
Delta Logo
9:24 am - 8:45 pm
MDW
-
KIX
21h 21m
2 stops
Delta Logo
12:35 pm - 10:36 pm
KIX
-
MDW
24h 01m
2 stops
$1,245Delta
Sun, Aug 30 - Sun, Sep 6
Delta Logo
7:25 pm - 8:45 pm
MDW
-
KIX
35h 20m
2 stops
Delta Logo
12:35 pm - 10:36 pm
KIX
-
MDW
24h 01m
2 stops
$1,261Delta
Sat, Aug 29 - Sat, Sep 5
Delta Logo
9:59 am - 10:40 pm
MDW
-
KIX
22h 41m
2 stops
Delta Logo
12:35 pm - 10:36 pm
KIX
-
MDW
24h 01m
2 stops
$1,295Delta
Thu, Aug 27 - Mon, Aug 31
Delta Logo
9:59 am - 8:45 pm
MDW
-
KIX
20h 46m
2 stops
Delta Logo
12:35 pm - 8:39 am
KIX
-
MDW
34h 04m
2 stops
$1,300Delta
Sat, Aug 8 - Sat, Aug 15
Multiple Airlines Logo
3:30 pm - 11:35 am
MDW
-
KIX
30h 05m
2 stops
Multiple Airlines Logo
7:00 pm - 5:55 am
KIX
-
MDW
25h 55m
2 stops
$1,430Multiple Airlines
Wed, Oct 28 - Mon, Nov 9
Multiple Airlines Logo
7:35 pm - 12:50 pm
MDW
-
KIX
27h 15m
2 stops
Multiple Airlines Logo
7:05 pm - 5:50 am
KIX
-
MDW
24h 45m
2 stops
$1,439Multiple Airlines
Wed, Sep 9 - Wed, Sep 23
Multiple Airlines Logo
7:05 pm - 11:35 am
MDW
-
KIX
26h 30m
2 stops
Multiple Airlines Logo
7:00 pm - 5:55 am
KIX
-
MDW
25h 55m
2 stops
$1,442Multiple Airlines
Sat, Oct 31 - Sat, Nov 14
Multiple Airlines Logo
3:55 pm - 11:35 am
MDW
-
KIX
29h 40m
2 stops
Multiple Airlines Logo
12:45 pm - 1:05 am
KIX
-
MDW
27h 20m
3 stops
$1,449Multiple Airlines
Mon, Oct 26 - Fri, Nov 6
Multiple Airlines Logo
4:45 pm - 11:35 am
MDW
-
KIX
27h 50m
2 stops
Multiple Airlines Logo
2:30 pm - 5:55 am
KIX
-
MDW
30h 25m
2 stops
$1,454Multiple Airlines
Sun, Nov 1 - Tue, Dec 1

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Delta flights from Chicago Midway Airport to Osaka

Our best Delta deals on Chicago Midway Airport to Osaka flight tickets
Delta
Aug 30
MDW5:10 pmChicago Midway
37h 35m
2 stops
KIX8:45 pmOsaka Kansai Intl
Sep 6
KIX12:35 pmOsaka Kansai Intl
24h 01m
2 stops
MDW10:36 pmChicago Midway
$1,214
Delta
Aug 30
MDW9:24 amChicago Midway
21h 21m
2 stops
KIX8:45 pmOsaka Kansai Intl
Sep 6
KIX12:35 pmOsaka Kansai Intl
24h 01m
2 stops
MDW10:36 pmChicago Midway
$1,245
Delta
Aug 29
MDW7:25 pmChicago Midway
35h 20m
2 stops
KIX8:45 pmOsaka Kansai Intl
Sep 5
KIX12:35 pmOsaka Kansai Intl
24h 01m
2 stops
MDW10:36 pmChicago Midway
$1,261

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 July 17, 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

Cheapest round-trip

ChicagoOsaka

MDW - KIX

MDWKIX

Chicago Midway

Sun 8/30

5:10 pm-8:45 pm

2 stops37h 35m

Osaka Kansai Intl

Sun 9/6

12:35 pm-10:36 pm

2 stops24h 01m

$1,214
Quickest round-trip

ChicagoOsaka

MDW - KIX

MDWKIX

Chicago Midway

Sun 8/30

9:24 am-8:45 pm

2 stops21h 21m

Osaka Kansai Intl

Sun 9/6

12:35 pm-10:36 pm

2 stops24h 01m

$1,245

ChicagoOsaka

MDW - KIX

MDWKIX

Chicago Midway

Sat 8/29

7:25 pm-8:45 pm

2 stops35h 20m

Osaka Kansai Intl

Sat 9/5

12:35 pm-10:36 pm

2 stops24h 01m

$1,261

ChicagoOsaka

MDW - KIX

MDWKIX

Chicago Midway

Thu 8/27

9:59 am-10:40 pm

2 stops22h 41m

Osaka Kansai Intl

Mon 8/31

12:35 pm-10:36 pm

2 stops24h 01m

$1,295

ChicagoOsaka

MDW - KIX

MDWKIX

Chicago Midway

Sat 8/8

9:59 am-8:45 pm

2 stops20h 46m

Osaka Kansai Intl

Sat 8/15

12:35 pm-8:39 am

2 stops34h 04m

$1,300

ChicagoOsaka

MDW - KIX

MDWKIX

Chicago Midway

Wed 10/28

3:30 pm-11:35 am

2 stops30h 05m

Osaka Kansai Intl

Mon 11/9

7:00 pm-5:55 am

2 stops25h 55m

$1,430

ChicagoOsaka

MDW - KIX

MDWKIX

Chicago Midway

Wed 9/9

7:35 pm-12:50 pm

2 stops27h 15m

Osaka Kansai Intl

Wed 9/23

7:05 pm-5:50 am

2 stops24h 45m

$1,439

ChicagoOsaka

MDW - KIX

MDWKIX

Chicago Midway

Sat 10/31

7:05 pm-11:35 am

2 stops26h 30m

Osaka Kansai Intl

Sat 11/14

7:00 pm-5:55 am

2 stops25h 55m

$1,442

ChicagoOsaka

MDW - KIX

MDWKIX

Chicago Midway

Mon 10/26

3:55 pm-11:35 am

2 stops29h 40m

Osaka Kansai Intl

Fri 11/6

12:45 pm-1:05 am

3 stops27h 20m

$1,449

ChicagoOsaka

MDW - KIX

MDWKIX

Chicago Midway

Sun 11/1

4:45 pm-11:35 am

2 stops27h 50m

Osaka Kansai Intl

Tue 12/1

2:30 pm-5:55 am

2 stops30h 25m

$1,454

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 19 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

22h 41m

Direct flights

None
The fastest flight from Chicago Midway Airport to Osaka takes 22h 41m
There are no direct flights from Chicago Midway Airport to Osaka. There are no popular flight routes from Chicago Midway Airport to Osaka.
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Frequently asked questions about flying from Chicago Midway Airport to Osaka

  • 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 22h 41m.

  • 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.

Frequently asked questions about flying from Chicago Midway Airport to Osaka

  • 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.

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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