$666 Cheap Flights from Chicago (MDW) to Osaka (KIX)

View $666 flight on Fri, May 15, 2026Opens in a new window

Popular airlines from Chicago Midway Airport (MDW) to Kansai Intl. Airport (KIX)

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Cheap Flights from Chicago to Osaka (MDW-KIX)

Prices were available within the past 7 days and start at $666 for one-way flights and $1,186 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Southwest Airlines
Wed, Mar 11 - Sat, Mar 14
MDW
Chicago
KIX
Osaka
$1,186 Roundtrip, found 5 days ago
$1,186
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Wed, Mar 11 from Chicago to Osaka, returning Sat, Mar 14, priced at $1,186 found 5 days ago
Southwest Airlines
Wed, Mar 11 - Sat, Mar 14
MDW
Chicago
KIX
Osaka
$1,195 Roundtrip, found 5 days ago
$1,195
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Wed, Mar 11 from Chicago to Osaka, returning Sat, Mar 14, priced at $1,195 found 5 days ago
Southwest Airlines
Wed, Mar 11 - Sat, Mar 14
MDW
Chicago
KIX
Osaka
$1,197 Roundtrip, found 5 days ago
$1,197
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Wed, Mar 11 from Chicago to Osaka, returning Sat, Mar 14, priced at $1,197 found 5 days ago
Southwest Airlines
Wed, Mar 11 - Sat, Mar 14
MDW
Chicago
KIX
Osaka
$1,199 Roundtrip, found 5 days ago
$1,199
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Wed, Mar 11 from Chicago to Osaka, returning Sat, Mar 14, priced at $1,199 found 5 days ago
Southwest Airlines
Wed, Mar 11 - Sat, Mar 14
MDW
Chicago
KIX
Osaka
$1,200 Roundtrip, found 5 days ago
$1,200
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Wed, Mar 11 from Chicago to Osaka, returning Sat, Mar 14, priced at $1,200 found 5 days ago
Southwest Airlines
Wed, Mar 11 - Sat, Mar 14
MDW
Chicago
KIX
Osaka
$1,203 Roundtrip, found 5 days ago
$1,203
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Wed, Mar 11 from Chicago to Osaka, returning Sat, Mar 14, priced at $1,203 found 5 days ago
Southwest Airlines
Mon, Mar 23 - Fri, Apr 10
MDW
Chicago
KIX
Osaka
$1,205 Roundtrip, found 17 hours ago
$1,205
Roundtrip
found 17 hours ago
Select Southwest Airlines flight, departing Mon, Mar 23 from Chicago to Osaka, returning Fri, Apr 10, priced at $1,205 found 17 hours ago
Delta
Thu, Jan 29 - Mon, Feb 16
MDW
Chicago
KIX
Osaka
$1,228 Roundtrip, found 4 days ago
$1,228
Roundtrip
found 4 days ago
Select Delta flight, departing Thu, Jan 29 from Chicago to Osaka, returning Mon, Feb 16, priced at $1,228 found 4 days ago
Air France
Wed, Nov 26 - Sat, Nov 29
MDW
Chicago
KIX
Osaka
$3,334 Roundtrip, found 12 hours ago
$3,334
Roundtrip
found 12 hours ago
Select Air France flight, departing Wed, Nov 26 from Chicago to Osaka, returning Sat, Nov 29, priced at $3,334 found 12 hours ago
KLM
Wed, Nov 26 - Sat, Nov 29
MDW
Chicago
KIX
Osaka
$3,345 Roundtrip, found 12 hours ago
$3,345
Roundtrip
found 12 hours ago
Select KLM flight, departing Wed, Nov 26 from Chicago to Osaka, returning Sat, Nov 29, priced at $3,345 found 12 hours ago

Alternative airports near Osaka

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to Itami ITM. Cheapest and Closest option available. Average driving time to city center is 10 minutes. Flights from $1,835
ITM
Itami
CheapestClosest
Average driving time to city center10 min
Flights from $1,835
Flights from Chicago (MDW) to Osaka (KIX)
Origin airport
Midway Intl.
Destination airport
Kansai Intl.
Airlines serving
Air France, Delta, KLM
Roundtrip price
$1,186
Distance
6507 mi

Chicago to Osaka Flights

The cheapest times to fly from Chicago to Osaka

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Chicago to Osaka are during the month of March. You can find some of the cheapest flights from Chicago to Osaka with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Chicago to Osaka

Sunday is one of the best days to book for cheap flights from Chicago to Osaka: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Chicago to Osaka

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Chicago to Osaka in 2025. You can also book with separate airlines for your outbound and return journeys, from $666 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Chicago to Osaka flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Chicago to Osaka airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Frequently asked questions

How much does a flight from Midway Intl. Airport (MDW) to Kansai Intl. Airport (KIX) cost?
Lock in a cheap one-way flight from $666 or cheap return flight from $1,186 from Midway Intl. Airport (MDW) to Kansai Intl. Airport (KIX) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to see our cheapest flight offers on this route.
What is the cheapest month to fly from Midway Intl. Airport (MDW) to Kansai Intl. Airport (KIX)?
Planning your getaway for March is a great way to save, as it's the cheapest month for flights between MDW and KIX. You'll often find the lowest fares during off-peak months.
What is the cheapest airline that flies from Midway Intl. Airport (MDW) to Kansai Intl. Airport (KIX)?
Use the filters on Expedia to compare airlines and find the most affordable carrier that'll fly you from MDW to KIX. Then, sort your results by "Price (lowest to highest)" to snag a good deal.
How many flights per day from Midway Intl. Airport (MDW) to Kansai Intl. Airport (KIX)?
You'll have to catch a flight with a layover when traveling from Midway Intl. Airport (MDW) to Kansai Intl. Airport (KIX). Direct flights don't operate daily on this route. However, simply filter your search to include one or more stops to find the best option for your trip.
What day of the week has the most flights from MDW to KIX?
Generally you'll find the most flight options available on a Friday. Tuesdays tend to be the quietest.* But this can vary based on the season, carrier and other factors.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Midway Intl. Airport (MDW) to Kansai Intl. Airport (KIX)?
Select a flight from Midway Intl. Airport (MDW) to Kansai Intl. Airport (KIX) that takes off before 3 PM to reduce the risk of cancellations and delays. Departures later than this have a 22% higher chance of being canceled, on average.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
Is it cheaper to buy a plane ticket from Midway Intl. Airport (MDW) to Kansai Intl. Airport (KIX) last-minute?
Booking your plane ticket from MDW to KIX just before your getaway is usually more expensive. But if there's some wiggle room with your departure dates and times, you could score a cheap last-minute fare.
Is it cheaper to book a MDW to KIX flight and hotel package?
Compared with arranging flights and hotels separately, booking a MDW to KIX flight and hotel package with Expedia could result in significant savings. Better yet, having everything in one easy place will take the hassle out of planning your trip. Simply secure your flights and choose from our wide range of hotels, then tailor your trip with extras like car rentals and activities.
Can I cancel or change the date of my flight from Midway Intl. Airport (MDW) to Kansai Intl. Airport (KIX)?
You can usually cancel or reschedule your MDW to KIX flight. However, if the booking was made more than 24 hours ago, additional charges may apply. Refer to your airline's policies in your itinerary to see what changes are possible and if any costs are involved. You'll also find further details on our Customer Service portal.

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*Available to One Key members.