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Cheap flights from Chicago Midway Airport to Osaka from $548

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
9:59 am - 10:40 pmMDW  Chicago Midway-KIX Osaka Kansai Intl
22h 41m2 stops Minneapolis St Paul Incheon Intl
Delta Logo
12:35 pm - 10:36 pmKIX  Osaka Kansai Intl-MDW Chicago Midway
24h 01m2 stops Incheon Intl Atlanta Hartsfield-Jackson
$1,196Delta
Thu, Aug 27 - Mon, Aug 31
Delta Logo
9:24 am - 8:45 pmMDW  Chicago Midway-KIX Osaka Kansai Intl
21h 21m2 stops Detroit Metropolitan Wayne County Incheon Intl
Delta Logo
12:35 pm - 10:44 pmKIX  Osaka Kansai Intl-MDW Chicago Midway
24h 09m2 stops Incheon Intl Atlanta Hartsfield-Jackson
$1,246Delta
Thu, Sep 3 - Thu, Sep 10
Delta Logo
9:24 am - 8:45 pmMDW  Chicago Midway-KIX Osaka Kansai Intl
21h 21m2 stops Detroit Metropolitan Wayne County Incheon Intl
Delta Logo
12:35 pm - 10:44 pmKIX  Osaka Kansai Intl-MDW Chicago Midway
24h 09m2 stops Incheon Intl Atlanta Hartsfield-Jackson
$1,282Delta
Thu, Aug 27 - Thu, Sep 10
Multiple Airlines Logo
3:45 pm - 11:35 amMDW  Chicago Midway-KIX Osaka Kansai Intl
28h 50m2 stops Los Angeles Taipei City Taiwan Taoyuan Intl
Multiple Airlines Logo
7:00 pm - 6:00 amKIX  Osaka Kansai Intl-MDW Chicago Midway
26h 00m2 stops Taipei City Taiwan Taoyuan Intl San Francisco
$1,292Multiple Airlines
Tue, Nov 17 - Thu, Nov 19
Delta Logo
9:29 am - 10:40 pmMDW  Chicago Midway-KIX Osaka Kansai Intl
23h 11m2 stops Detroit Metropolitan Wayne County Incheon Intl
Delta Logo
2:15 am - 6:33 pmKIX  Osaka Kansai Intl-MDW Chicago Midway
30h 18m2 stops Incheon Intl Detroit Metropolitan Wayne County
$1,295Delta
Tue, Sep 8 - Mon, Sep 14
Delta Logo
5:10 pm - 11:20 amMDW  Chicago Midway-KIX Osaka Kansai Intl
28h 10m2 stops Atlanta Hartsfield-Jackson Incheon Intl
Delta Logo
9:05 am - 10:44 pmKIX  Osaka Kansai Intl-MDW Chicago Midway
27h 39m2 stops Incheon Intl Atlanta Hartsfield-Jackson
$1,296Delta
Fri, Sep 4 - Fri, Sep 11
Multiple Airlines Logo
8:45 pm - 12:00 pmMDW  Chicago Midway-KIX Osaka Kansai Intl
25h 15m2 stops Los Angeles Taipei City Taiwan Taoyuan Intl
Multiple Airlines Logo
2:30 pm - 5:55 amKIX  Osaka Kansai Intl-MDW Chicago Midway
30h 25m2 stops Taipei City Taiwan Taoyuan Intl Los Angeles
$1,297Multiple Airlines
Tue, Sep 8 - Mon, Dec 7
Multiple Airlines Logo
5:55 pm - 12:50 pmMDW  Chicago Midway-KIX Osaka Kansai Intl
28h 55m2 stops Los Angeles Taipei City Taiwan Taoyuan Intl
Multiple Airlines Logo
7:05 pm - 12:00 pmKIX  Osaka Kansai Intl-MDW Chicago Midway
30h 55m2 stops Taipei City Taiwan Taoyuan Intl Los Angeles
$1,298Multiple Airlines
Mon, Aug 17 - Mon, Aug 31
Multiple Airlines Logo
8:45 pm - 12:00 pmMDW  Chicago Midway-KIX Osaka Kansai Intl
25h 15m2 stops Los Angeles Taipei City Taiwan Taoyuan Intl
Multiple Airlines Logo
7:05 pm - 5:50 amKIX  Osaka Kansai Intl-MDW Chicago Midway
24h 45m2 stops Taipei City Taiwan Taoyuan Intl San Francisco
$1,309Multiple Airlines
Thu, Aug 27 - Mon, Aug 31
Multiple Airlines Logo
8:45 pm - 12:00 pmMDW  Chicago Midway-KIX Osaka Kansai Intl
25h 15m2 stops Los Angeles Taipei City Taiwan Taoyuan Intl
Multiple Airlines Logo
2:00 pm - 5:45 amKIX  Osaka Kansai Intl-MDW Chicago Midway
29h 45m2 stops Taipei City Taiwan Taoyuan Intl Ontario
$1,310Multiple Airlines
Thu, Aug 27 - Mon, Aug 31

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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 27
MDW9:59 amChicago Midway
22h 41m
2 stops
KIX10:40 pmOsaka Kansai Intl
Aug 31
KIX12:35 pmOsaka Kansai Intl
24h 01m
2 stops
MDW10:36 pmChicago Midway
$1,196
Delta
Sep 16
MDW9:59 amChicago Midway
35h 21m
2 stops
KIX11:20 amOsaka Kansai Intl
Sep 23
KIX9:05 amOsaka Kansai Intl
27h 39m
2 stops
MDW10:44 pmChicago Midway
$1,245
Delta
Sep 3
MDW9:24 amChicago Midway
21h 21m
2 stops
KIX8:45 pmOsaka Kansai Intl
Sep 10
KIX12:35 pmOsaka Kansai Intl
24h 09m
2 stops
MDW10:44 pmChicago Midway
$1,246

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 August 7, 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 Chicago Midway - KIX Osaka Kansai Intl

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

$1,196
Quickest round-trip

ChicagoOsaka

MDW Chicago Midway - KIX Osaka Kansai Intl

MDWKIX

Chicago Midway

Thu 9/3

9:24 am-8:45 pm

2 stops21h 21m

Osaka Kansai Intl

Thu 9/10

12:35 pm-10:44 pm

2 stops24h 09m

$1,246

ChicagoOsaka

MDW Chicago Midway - KIX Osaka Kansai Intl

MDWKIX

Chicago Midway

Thu 8/27

9:24 am-8:45 pm

2 stops21h 21m

Osaka Kansai Intl

Thu 9/10

12:35 pm-10:44 pm

2 stops24h 09m

$1,282

ChicagoOsaka

MDW Chicago Midway - KIX Osaka Kansai Intl

MDWKIX

Chicago Midway

Tue 11/17

3:45 pm-11:35 am

2 stops28h 50m

Osaka Kansai Intl

Thu 11/19

7:00 pm-6:00 am

2 stops26h 00m

$1,292

ChicagoOsaka

MDW Chicago Midway - KIX Osaka Kansai Intl

MDWKIX

Chicago Midway

Tue 9/8

9:29 am-10:40 pm

2 stops23h 11m

Osaka Kansai Intl

Mon 9/14

2:15 am-6:33 pm

2 stops30h 18m

$1,295

ChicagoOsaka

MDW Chicago Midway - KIX Osaka Kansai Intl

MDWKIX

Chicago Midway

Fri 9/4

5:10 pm-11:20 am

2 stops28h 10m

Osaka Kansai Intl

Fri 9/11

9:05 am-10:44 pm

2 stops27h 39m

$1,296

ChicagoOsaka

MDW Chicago Midway - KIX Osaka Kansai Intl

MDWKIX

Chicago Midway

Tue 9/8

8:45 pm-12:00 pm

2 stops25h 15m

Osaka Kansai Intl

Mon 12/7

2:30 pm-5:55 am

2 stops30h 25m

$1,297

ChicagoOsaka

MDW Chicago Midway - KIX Osaka Kansai Intl

MDWKIX

Chicago Midway

Mon 8/17

5:55 pm-12:50 pm

2 stops28h 55m

Osaka Kansai Intl

Mon 8/31

7:05 pm-12:00 pm

2 stops30h 55m

$1,298

ChicagoOsaka

MDW Chicago Midway - KIX Osaka Kansai Intl

MDWKIX

Chicago Midway

Thu 8/27

8:45 pm-12:00 pm

2 stops25h 15m

Osaka Kansai Intl

Mon 8/31

7:05 pm-5:50 am

2 stops24h 45m

$1,309

ChicagoOsaka

MDW Chicago Midway - KIX Osaka Kansai Intl

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

$1,310

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

21h 21m

Direct flights

None
The fastest flight from Chicago Midway Airport to Osaka takes 21h 21m
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 21h 21m.

  • 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