$749 Cheap Flights from Osaka (KIX) to Chicago (MDW)

View $749 flight on Tue, Jun 9, 2026Opens in a new window

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

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Cheap Flights from Osaka to Chicago (KIX-MDW)

Prices were available within the past 7 days and start at $749 for one-way flights and $1,592 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

China Airlines
Mon, Jul 27 - Mon, Sep 7
KIX
Osaka
MDW
Chicago
$1,592 Roundtrip, found 21 hours ago
$1,592
Roundtrip
found 21 hours ago
Select China Airlines flight, departing Mon, Jul 27 from Osaka to Chicago, returning Mon, Sep 7, priced at $1,592 found 21 hours ago
China Airlines
Tue, Jul 28 - Mon, Aug 17
KIX
Osaka
MDW
Chicago
$1,665 Roundtrip, found 4 days ago
$1,665
Roundtrip
found 4 days ago
Select China Airlines flight, departing Tue, Jul 28 from Osaka to Chicago, returning Mon, Aug 17, priced at $1,665 found 4 days ago
China Airlines
Tue, Jun 16 - Wed, Jun 17
KIX
Osaka
MDW
Chicago
$1,739 Roundtrip, found 5 days ago
$1,739
Roundtrip
found 5 days ago
Select China Airlines flight, departing Tue, Jun 16 from Osaka to Chicago, returning Wed, Jun 17, priced at $1,739 found 5 days ago
China Airlines
Tue, Jul 28 - Mon, Aug 17
KIX
Osaka
MDW
Chicago
$1,754 Roundtrip, found 4 days ago
$1,754
Roundtrip
found 4 days ago
Select China Airlines flight, departing Tue, Jul 28 from Osaka to Chicago, returning Mon, Aug 17, priced at $1,754 found 4 days ago
EVA Airways
Wed, Apr 29 - Wed, May 6
KIX
Osaka
MDW
Chicago
$1,798 Roundtrip, found 4 days ago
$1,798
Roundtrip
found 4 days ago
Select EVA Airways flight, departing Wed, Apr 29 from Osaka to Chicago, returning Wed, May 6, priced at $1,798 found 4 days ago
China Airlines
Mon, Jul 27 - Mon, Sep 7
KIX
Osaka
MDW
Chicago
$1,853 Roundtrip, found 21 hours ago
$1,853
Roundtrip
found 21 hours ago
Select China Airlines flight, departing Mon, Jul 27 from Osaka to Chicago, returning Mon, Sep 7, priced at $1,853 found 21 hours ago
EVA Airways
Tue, Jul 28 - Mon, Aug 17
KIX
Osaka
MDW
Chicago
$1,905 Roundtrip, found 4 days ago
$1,905
Roundtrip
found 4 days ago
Select EVA Airways flight, departing Tue, Jul 28 from Osaka to Chicago, returning Mon, Aug 17, priced at $1,905 found 4 days ago
Delta
Tue, Jul 28 - Mon, Aug 17
KIX
Osaka
MDW
Chicago
$2,316 Roundtrip, found 4 days ago
$2,316
Roundtrip
found 4 days ago
Select Delta flight, departing Tue, Jul 28 from Osaka to Chicago, returning Mon, Aug 17, priced at $2,316 found 4 days ago
All Nippon Airways
Wed, Apr 29 - Wed, May 6
KIX
Osaka
MDW
Chicago
$2,501 Roundtrip, found 4 days ago
$2,501
Roundtrip
found 4 days ago
Select All Nippon Airways flight, departing Wed, Apr 29 from Osaka to Chicago, returning Wed, May 6, priced at $2,501 found 4 days ago
Korean Air
Mon, Jun 1 - Mon, Jun 8
KIX
Osaka
MDW
Chicago
$7,176 Roundtrip, found 2 days ago
$7,176
Roundtrip
found 2 days ago
Select Korean Air flight, departing Mon, Jun 1 from Osaka to Chicago, returning Mon, Jun 8, priced at $7,176 found 2 days ago

Alternative airports near Chicago

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

Select flight to O'Hare Intl. ORD. Cheapest option available. Average driving time to city center is 23 minutes. Flights from $1,693
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $1,693

Frequently asked questions

How much does a flight from Kansai Intl. Airport (KIX) to Midway Intl. Airport (MDW) cost?
Snag a cheap one-way flight from $749 or cheap return flight from $1,592 from Kansai Intl. Airport (KIX) to Midway Intl. Airport (MDW) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight deals on this route.
What is the cheapest month to fly from Kansai Intl. Airport (KIX) to Midway Intl. Airport (MDW)?
July is the most affordable month to fly from KIX to MDW. Avoiding peak travel times is often the key to finding a great deal.
What is the cheapest airline that flies from Kansai Intl. Airport (KIX) to Midway Intl. Airport (MDW)?
Use the filters on Expedia to compare different airlines and find the most affordable carrier that'll fly you from KIX to MDW. Then, sort your results by "Price (lowest to highest)" to snap up a great deal.
How many flights per day from Kansai Intl. Airport (KIX) to Midway Intl. Airport (MDW)?
Direct flights from Kansai Intl. Airport (KIX) to Midway Intl. Airport (MDW) aren't available daily, so you'll need to take a flight with a layover. Explore your options with our filter tool. Enter your travel dates and click on either "1 Stop" or "2+ Stops."
What day of the week has the most flights from KIX to MDW?
Usually you'll find the greatest selection of flight options on a Friday. Tuesdays are often the quietest.* But this can vary based on the season, airline 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 Kansai Intl. Airport (KIX) to Midway Intl. Airport (MDW)?
Choose a flight from Kansai Intl. Airport (KIX) to Midway Intl. Airport (MDW) that takes off before 3 PM to reduce the likelihood of delays. Later departures 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 Kansai Intl. Airport (KIX) to Midway Intl. Airport (MDW) last-minute?
Holding off until right before your break to book a ticket from KIX to MDW generally means paying more. Although you may find some last-minute discounts, they're not always guaranteed. Be flexible with your travel plans for the best chance of getting a bargain.
Is it cheaper to book a KIX to MDW flight and hotel package?
Booking a KIX to MDW flight and hotel package is usually cheaper than booking separately. With Expedia, you can enjoy the convenience of organizing your trip in one place. Select from our wide range of hotels and then add flights, car rentals and activities to your booking. Bundle everything together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Kansai Intl. Airport (KIX) to Midway Intl. Airport (MDW)?
In most cases, you're able to reschedule or cancel your KIX to MDW flight. However, there may be additional charges, especially if you booked over 24 hours ago. Check your itinerary for the airline's fees and rules on flight changes, or if you need more details, go to our Customer Service portal.

Travel information

Origin airport
Kansai Intl.
Destination airport
Midway Intl.
Airlines serving
Delta
Roundtrip price
$1,592
Distance
6507 mi

Book with confidence

Osaka to Chicago Flights

The cheapest times to fly from Osaka to Chicago

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 Osaka to Chicago are during the month of July. You can find some of the cheapest flights from Osaka to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Osaka to Chicago

Sunday is one of the best days to book for cheap flights from Osaka to Chicago: 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 Osaka to Chicago

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 Osaka to Chicago in 2026. You can also book with separate airlines for your outbound and return journeys, from $749 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 Osaka to Chicago 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 Osaka to Chicago 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.

 

Osaka to Chicago Flights

*Flight schedules are subject to change.

*Available to One Key members.

 

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