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Cheap flights from Chicago Midway Airport to Osaka from $442

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 9/8. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
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.
Multiple Airlines Logo
8:40 pm - 9:55 am
MDW
-
KIX
23h 15m
2 stops
Multiple Airlines Logo
6:10 pm - 5:55 am
KIX
-
MDW
26h 45m
2 stops
$1,469Multiple Airlines
Wed, Oct 28 - Wed, Nov 11
Multiple Airlines Logo
8:40 pm - 9:55 am
MDW
-
KIX
23h 15m
2 stops
Multiple Airlines Logo
6:10 pm - 5:55 am
KIX
-
MDW
26h 45m
2 stops
$1,470Multiple Airlines
Wed, Oct 28 - Wed, Nov 11
Multiple Airlines Logo
3:35 pm - 11:35 am
MDW
-
KIX
30h 00m
2 stops
Multiple Airlines Logo
2:30 pm - 5:40 am
KIX
-
MDW
30h 10m
2 stops
$1,490Multiple Airlines
Wed, Oct 28 - Mon, Nov 9
Multiple Airlines Logo
8:30 pm - 10:10 am
MDW
-
KIX
23h 40m
2 stops
Multiple Airlines Logo
6:30 pm - 5:50 am
KIX
-
MDW
25h 20m
2 stops
$1,509Multiple Airlines
Tue, Sep 8 - Sat, Sep 26
Multiple Airlines Logo
8:45 pm - 12:00 pm
MDW
-
KIX
25h 15m
2 stops
Multiple Airlines Logo
2:00 pm - 5:45 am
KIX
-
MDW
29h 45m
2 stops
$1,521Multiple Airlines
Thu, Aug 27 - Mon, Aug 31
Multiple Airlines Logo
8:45 pm - 12:00 pm
MDW
-
KIX
25h 15m
2 stops
Multiple Airlines Logo
7:05 pm - 5:05 am
KIX
-
MDW
24h 00m
2 stops
$1,544Multiple Airlines
Thu, Sep 3 - Sun, Sep 13
Multiple Airlines Logo
6:25 pm - 12:50 pm
MDW
-
KIX
28h 25m
2 stops
Multiple Airlines Logo
7:05 pm - 5:05 am
KIX
-
MDW
24h 00m
2 stops
$1,545Multiple Airlines
Sat, Aug 22 - Sat, Sep 5
Multiple Airlines Logo
6:20 pm - 10:10 am
MDW
-
KIX
25h 50m
2 stops
Multiple Airlines Logo
6:10 pm - 6:05 am
KIX
-
MDW
25h 55m
2 stops
$1,547Multiple Airlines
Sun, Oct 18 - Wed, Oct 28
Multiple Airlines Logo
8:55 pm - 10:10 am
MDW
-
KIX
23h 15m
2 stops
Multiple Airlines Logo
6:30 pm - 5:55 am
KIX
-
MDW
25h 25m
2 stops
$1,550Multiple Airlines
Fri, Sep 4 - Sat, Sep 12
Multiple Airlines Logo
3:35 pm - 11:35 am
MDW
-
KIX
30h 00m
2 stops
Multiple Airlines Logo
7:00 pm - 5:55 am
KIX
-
MDW
25h 55m
2 stops
$1,557Multiple Airlines
Wed, Oct 28 - Mon, Nov 9

Delta flights from Chicago Midway Airport to Osaka

Our best Delta deals on Chicago Midway Airport to Osaka flight tickets
Delta
May 15
MDW9:23 amChicago Midway
23h 17m
2 stops
KIX10:40 pmOsaka Kansai Intl
May 23
KIX2:15 amOsaka Kansai Intl
32h 54m
2 stops
MDW9:09 pmChicago Midway
$2,421
Delta
May 12
MDW9:22 amChicago Midway
21h 23m
2 stops
KIX8:45 pmOsaka Kansai Intl
May 24
KIX9:05 amOsaka Kansai Intl
26h 04m
2 stops
MDW9:09 pmChicago Midway
$3,194
Delta
May 12
MDW9:22 amChicago Midway
21h 23m
2 stops
KIX8:45 pmOsaka Kansai Intl
May 23
KIX2:15 amOsaka Kansai Intl
30h 18m
2 stops
MDW6:33 pmChicago Midway
$3,195

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 May 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

Cheapest round-trip

ChicagoOsaka

MDW - KIX

MDWKIX

Chicago Midway

Wed 10/28

8:40 pm-9:55 am

2 stops23h 15m

Osaka Kansai Intl

Wed 11/11

6:10 pm-5:55 am

2 stops26h 45m

$1,469

ChicagoOsaka

MDW - KIX

MDWKIX

Chicago Midway

Wed 10/28

8:40 pm-9:55 am

2 stops23h 15m

Osaka Kansai Intl

Wed 11/11

6:10 pm-5:55 am

2 stops26h 45m

$1,470

ChicagoOsaka

MDW - KIX

MDWKIX

Chicago Midway

Wed 10/28

3:35 pm-11:35 am

2 stops30h 00m

Osaka Kansai Intl

Mon 11/9

2:30 pm-5:40 am

2 stops30h 10m

$1,490

ChicagoOsaka

MDW - KIX

MDWKIX

Chicago Midway

Tue 9/8

8:30 pm-10:10 am

2 stops23h 40m

Osaka Kansai Intl

Sat 9/26

6:30 pm-5:50 am

2 stops25h 20m

$1,509

ChicagoOsaka

MDW - KIX

MDWKIX

Chicago Midway

Thu 8/27

8:45 pm-12:00 pm

2 stops25h 15m

Osaka Kansai Intl

Mon 8/31

2:00 pm-5:45 am

2 stops29h 45m

$1,521

ChicagoOsaka

MDW - KIX

MDWKIX

Chicago Midway

Thu 9/3

8:45 pm-12:00 pm

2 stops25h 15m

Osaka Kansai Intl

Sun 9/13

7:05 pm-5:05 am

2 stops24h 00m

$1,544

ChicagoOsaka

MDW - KIX

MDWKIX

Chicago Midway

Sat 8/22

6:25 pm-12:50 pm

2 stops28h 25m

Osaka Kansai Intl

Sat 9/5

7:05 pm-5:05 am

2 stops24h 00m

$1,545

ChicagoOsaka

MDW - KIX

MDWKIX

Chicago Midway

Sun 10/18

6:20 pm-10:10 am

2 stops25h 50m

Osaka Kansai Intl

Wed 10/28

6:10 pm-6:05 am

2 stops25h 55m

$1,547
Quickest round-trip

ChicagoOsaka

MDW - KIX

MDWKIX

Chicago Midway

Fri 9/4

8:55 pm-10:10 am

2 stops23h 15m

Osaka Kansai Intl

Sat 9/12

6:30 pm-5:55 am

2 stops25h 25m

$1,550

ChicagoOsaka

MDW - KIX

MDWKIX

Chicago Midway

Wed 10/28

3:35 pm-11:35 am

2 stops30h 00m

Osaka Kansai Intl

Mon 11/9

7:00 pm-5:55 am

2 stops25h 55m

$1,557

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

23h 15m

Direct flights

None
The fastest flight from Chicago Midway Airport to Osaka takes 23h 15m
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

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 23h 15m.

  • 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.

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