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Cheap flights from Chicago Midway Airport to Osaka from $502

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 5/6. 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

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
7:05 pm - 12:00 pm
MDW
-
KIX
26h 55m
2 stops
Multiple Airlines Logo
7:05 pm - 6:05 am
KIX
-
MDW
25h 00m
2 stops
$1,272Multiple Airlines
Sat, Oct 10 - Tue, Oct 20
Multiple Airlines Logo
8:45 pm - 12:50 pm
MDW
-
KIX
26h 05m
2 stops
Multiple Airlines Logo
2:00 pm - 5:45 am
KIX
-
MDW
29h 45m
2 stops
$1,331Multiple Airlines
Thu, Aug 27 - Mon, Aug 31
Delta Logo
9:20 am - 10:40 pm
MDW
-
KIX
23h 20m
2 stops
Delta Logo
12:35 pm - 9:46 pm
KIX
-
MDW
23h 11m
2 stops
$1,477Delta
Tue, Sep 8 - Tue, Sep 22
Multiple Airlines Logo
6:25 pm - 12:00 pm
MDW
-
KIX
27h 35m
2 stops
Multiple Airlines Logo
7:05 pm - 6:05 am
KIX
-
MDW
25h 00m
2 stops
$1,493Multiple Airlines
Sat, Sep 26 - Mon, Oct 5
Delta Logo
9:30 am - 10:40 pm
MDW
-
KIX
23h 10m
2 stops
Delta Logo
2:15 am - 12:30 pm
KIX
-
MDW
24h 15m
2 stops
$1,533Delta
Sat, Sep 12 - Mon, Sep 21
Multiple Airlines Logo
8:50 pm - 12:50 pm
MDW
-
KIX
26h 00m
2 stops
Multiple Airlines Logo
7:05 pm - 5:55 am
KIX
-
MDW
24h 50m
2 stops
$1,552Multiple Airlines
Tue, Sep 15 - Thu, Sep 24
Delta Logo
9:30 am - 8:45 pm
MDW
-
KIX
21h 15m
2 stops
Delta Logo
2:15 am - 12:33 pm
KIX
-
MDW
25h 18m
2 stops
$1,577Delta
Mon, Sep 28 - Sun, Nov 15
Multiple Airlines Logo
6:00 pm - 12:00 pm
MDW
-
KIX
28h 00m
2 stops
Multiple Airlines Logo
7:05 pm - 5:50 am
KIX
-
MDW
24h 45m
2 stops
$1,640Multiple Airlines
Sat, May 2 - Sat, May 9
Multiple Airlines Logo
6:25 pm - 12:00 pm
MDW
-
KIX
27h 35m
2 stops
Multiple Airlines Logo
7:05 pm - 5:05 am
KIX
-
MDW
24h 00m
2 stops
$1,675Multiple Airlines
Sat, Aug 15 - Thu, Aug 27
Delta Logo
4:30 pm - 10:40 pm
MDW
-
KIX
40h 10m
2 stops
Delta Logo
2:15 am - 12:33 pm
KIX
-
MDW
25h 18m
2 stops
$1,677Delta
Sat, Sep 26 - Fri, Nov 13

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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
Sep 8
MDW9:20 amChicago Midway
23h 20m
2 stops
KIX10:40 pmOsaka Kansai Intl
Sep 22
KIX12:35 pmOsaka Kansai Intl
23h 11m
2 stops
MDW9:46 pmChicago Midway
$1,477
Delta
Sep 12
MDW9:30 amChicago Midway
23h 10m
2 stops
KIX10:40 pmOsaka Kansai Intl
Sep 21
KIX2:15 amOsaka Kansai Intl
24h 15m
2 stops
MDW12:30 pmChicago Midway
$1,533
Delta
Sep 28
MDW9:30 amChicago Midway
21h 15m
2 stops
KIX8:45 pmOsaka Kansai Intl
Nov 15
KIX2:15 amOsaka Kansai Intl
25h 18m
2 stops
MDW12:33 pmChicago Midway
$1,577

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 April 18, 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

Sat 10/10

7:05 pm-12:00 pm

2 stops26h 55m

Osaka Kansai Intl

Tue 10/20

7:05 pm-6:05 am

2 stops25h 00m

$1,272

ChicagoOsaka

MDW - KIX

MDWKIX

Chicago Midway

Thu 8/27

8:45 pm-12:50 pm

2 stops26h 05m

Osaka Kansai Intl

Mon 8/31

2:00 pm-5:45 am

2 stops29h 45m

$1,331
Quickest round-trip

ChicagoOsaka

MDW - KIX

MDWKIX

Chicago Midway

Tue 9/8

9:20 am-10:40 pm

2 stops23h 20m

Osaka Kansai Intl

Tue 9/22

12:35 pm-9:46 pm

2 stops23h 11m

$1,477

ChicagoOsaka

MDW - KIX

MDWKIX

Chicago Midway

Sat 9/26

6:25 pm-12:00 pm

2 stops27h 35m

Osaka Kansai Intl

Mon 10/5

7:05 pm-6:05 am

2 stops25h 00m

$1,493

ChicagoOsaka

MDW - KIX

MDWKIX

Chicago Midway

Sat 9/12

9:30 am-10:40 pm

2 stops23h 10m

Osaka Kansai Intl

Mon 9/21

2:15 am-12:30 pm

2 stops24h 15m

$1,533

ChicagoOsaka

MDW - KIX

MDWKIX

Chicago Midway

Tue 9/15

8:50 pm-12:50 pm

2 stops26h 00m

Osaka Kansai Intl

Thu 9/24

7:05 pm-5:55 am

2 stops24h 50m

$1,552

ChicagoOsaka

MDW - KIX

MDWKIX

Chicago Midway

Mon 9/28

9:30 am-8:45 pm

2 stops21h 15m

Osaka Kansai Intl

Sun 11/15

2:15 am-12:33 pm

2 stops25h 18m

$1,577

ChicagoOsaka

MDW - KIX

MDWKIX

Chicago Midway

Sat 5/2

6:00 pm-12:00 pm

2 stops28h 00m

Osaka Kansai Intl

Sat 5/9

7:05 pm-5:50 am

2 stops24h 45m

$1,640

ChicagoOsaka

MDW - KIX

MDWKIX

Chicago Midway

Sat 8/15

6:25 pm-12:00 pm

2 stops27h 35m

Osaka Kansai Intl

Thu 8/27

7:05 pm-5:05 am

2 stops24h 00m

$1,675

ChicagoOsaka

MDW - KIX

MDWKIX

Chicago Midway

Sat 9/26

4:30 pm-10:40 pm

2 stops40h 10m

Osaka Kansai Intl

Fri 11/13

2:15 am-12:33 pm

2 stops25h 18m

$1,677

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Osaka from

How to get the cheapest flight ticket from Chicago Midway Airport to Osaka

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest airline that flies from Chicago Midway to Osaka?

Delta is the most popular carrier operating from Chicago Midway to Osaka

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

20h 56m

Direct flights

None
The fastest flight from Chicago Midway Airport to Osaka takes 20h 56m
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 20h 56m.

  • 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.

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