How do I get Price Alerts for flights from Osaka to Chicago Midway Airport?

Search flight deals from Osaka to Chicago Midway Airport . While viewing offers you’ll have the option to create a Price Alert.

How can I save money on flights from Osaka to Chicago Midway Airport with momondo?

With “Price Forecast”, learn how soon you should book your flight in advance. Down to the day of week and time of day, our information can inform you on the ideal time to book to save on your travel. Our “Price Calendar” shows you at a quick glance when to book your travel for lower rates. By setting “Price Alerts” you can monitor changes in price and target the ideal time to book. Search for your trip destination by budget amount via our “Explore” feature. Whether you’re looking for ideas for your next travel adventure or cost-cutting tips, our “Discover” content is a great place to start.

How does momondo find its flight prices?

momondo shows deals across 700+ competitors all at once. momondo is active in 30 international markets, so you can have access to a wide range of options from airlines and OTAs alike.

When did momondo last update prices for flights from Osaka to Chicago Midway Airport?

Prices for flights from Osaka to Chicago Midway Airport refresh daily.

How old do you have to be to fly from Osaka to Chicago Midway Airport?

Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Osaka to Chicago Midway Airport.

What documentation or ID do you need to fly to Chicago Midway Airport?

The travel and health documents required for your trip to Chicago Midway Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago Midway Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

$512 Cheap Flights from Osaka to Chicago Midway Airport in 2026/27

Find the cheapest flights from Osaka to Chicago

Round-trip

One-way

Last minute

Cheap round-trip flights

Enter your travel dates to find the best prices.

7:05 pm - 5:50 amKIX Osaka Kansai Intl-MDW Chicago Midway

24h 45m2 stops Taipei City Taiwan Taoyuan Intl Los Angeles Los Angeles

7:00 pm - 1:20 pmMDW Chicago Midway-KIX Osaka Kansai Intl

28h 20m2 stops Ontario Taipei City Taiwan Taoyuan Intl

$1,487Multiple Airlines

Tue, Oct 20 - Sat, Oct 24

7:05 pm - 5:50 amKIX Osaka Kansai Intl-MDW Chicago Midway

24h 45m2 stops Taipei City Taiwan Taoyuan Intl Los Angeles Los Angeles

7:00 pm - 1:20 pmMDW Chicago Midway-KIX Osaka Kansai Intl

28h 20m2 stops Ontario Taipei City Taiwan Taoyuan Intl

$1,491Multiple Airlines

Tue, Oct 20 - Sat, Oct 24

7:00 pm - 5:55 amKIX Osaka Kansai Intl-MDW Chicago Midway

25h 55m2 stops Taipei City Taiwan Taoyuan Intl Los Angeles Los Angeles

6:00 pm - 11:35 amMDW Chicago Midway-KIX Osaka Kansai Intl

26h 35m2 stops Los Angeles Los Angeles Taipei City Taiwan Taoyuan Intl

$1,504Multiple Airlines

Mon, Dec 21 - Sat, Jan 9

7:05 pm - 5:50 amKIX Osaka Kansai Intl-MDW Chicago Midway

24h 45m2 stops Taipei City Taiwan Taoyuan Intl Los Angeles Los Angeles

7:45 pm - 1:20 pmMDW Chicago Midway-KIX Osaka Kansai Intl

27h 35m2 stops Los Angeles Los Angeles Taipei City Taiwan Taoyuan Intl

$1,505Multiple Airlines

Tue, Oct 20 - Sat, Oct 24

2:30 pm - 5:40 amKIX Osaka Kansai Intl-MDW Chicago Midway

30h 10m2 stops Taipei City Taiwan Taoyuan Intl Ontario

3:45 pm - 11:35 amMDW Chicago Midway-KIX Osaka Kansai Intl

28h 50m2 stops Phoenix Sky Harbor Intl Taipei City Taiwan Taoyuan Intl

$1,527Multiple Airlines

Thu, Dec 17 - Fri, Jan 8

2:30 pm - 5:40 amKIX Osaka Kansai Intl-MDW Chicago Midway

30h 10m2 stops Taipei City Taiwan Taoyuan Intl Ontario

6:00 pm - 1:20 pmMDW Chicago Midway-KIX Osaka Kansai Intl

28h 20m2 stops Los Angeles Los Angeles Taipei City Taiwan Taoyuan Intl

$1,543Multiple Airlines

Thu, Dec 17 - Sat, Jan 9

7:05 pm - 5:50 amKIX Osaka Kansai Intl-MDW Chicago Midway

24h 45m2 stops Taipei City Taiwan Taoyuan Intl San Francisco

6:30 pm - 11:35 amMDW Chicago Midway-KIX Osaka Kansai Intl

27h 05m2 stops Los Angeles Los Angeles Taipei City Taiwan Taoyuan Intl

$1,552Multiple Airlines

Thu, Oct 22 - Sun, Oct 25

2:30 pm - 5:40 amKIX Osaka Kansai Intl-MDW Chicago Midway

30h 10m2 stops Taipei City Taiwan Taoyuan Intl Ontario

3:50 pm - 1:20 pmMDW Chicago Midway-KIX Osaka Kansai Intl

30h 30m2 stops Los Angeles Los Angeles Taipei City Taiwan Taoyuan Intl

$1,567Multiple Airlines

Thu, Dec 17 - Fri, Jan 8

2:30 pm - 5:40 amKIX Osaka Kansai Intl-MDW Chicago Midway

30h 10m2 stops Taipei City Taiwan Taoyuan Intl Ontario

3:45 pm - 1:20 pmMDW Chicago Midway-KIX Osaka Kansai Intl

30h 35m2 stops Phoenix Sky Harbor Intl Taipei City Taiwan Taoyuan Intl

$1,573Multiple Airlines

Thu, Dec 17 - Fri, Jan 8

9:30 am - 11:43 pmKIX Osaka Kansai Intl-MDW Chicago Midway

28h 13m3 stops Shanghai Pu Dong Los Angeles Los Angeles Atlanta Hartsfield-Jackson

3:30 pm - 9:55 amMDW Chicago Midway-KIX Osaka Kansai Intl

28h 25m2 stops Dallas/Fort Worth Taipei City Taiwan Taoyuan Intl

$1,581Multiple Airlines

Tue, Oct 20 - Sat, Oct 24

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Delta flights from Osaka to Chicago Midway Airport

Our best Delta deals on Osaka to Chicago Midway Airport flight tickets

Delta

Dec 2

KIX2:15 amOsaka Kansai Intl

30h 46m

2 stops

MDW6:01 pmChicago Midway

Dec 7

MDW1:41 pmChicago Midway

54h 04m

2 stops

KIX10:45 amOsaka Kansai Intl

$1,776

Delta

Dec 2

KIX2:15 amOsaka Kansai Intl

30h 46m

2 stops

MDW6:01 pmChicago Midway

Dec 7

MDW1:41 pmChicago Midway

54h 04m

2 stops

KIX10:45 amOsaka Kansai Intl

$2,090

Delta

Dec 2

KIX2:15 amOsaka Kansai Intl

30h 46m

2 stops

MDW6:01 pmChicago Midway

Dec 7

MDW1:41 pmChicago Midway

54h 04m

2 stops

KIX10:45 amOsaka Kansai Intl

$2,101

momondo Fare Finder

Use the filters below to find and compare flights from Osaka to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

OsakaChicago

KIX Osaka Kansai Intl - MDW Chicago Midway

KIXMDW

Osaka Kansai Intl

Tue 10/20

7:05 pm-5:50 am

2 stops24h 45m

Chicago Midway

Sat 10/24

7:00 pm-1:20 pm

2 stops28h 20m

$1,487

OsakaChicago

KIX Osaka Kansai Intl - MDW Chicago Midway

KIXMDW

Osaka Kansai Intl

Tue 10/20

7:05 pm-5:50 am

2 stops24h 45m

Chicago Midway

Sat 10/24

7:00 pm-1:20 pm

2 stops28h 20m

$1,491

OsakaChicago

KIX Osaka Kansai Intl - MDW Chicago Midway

KIXMDW

Osaka Kansai Intl

Mon 12/21

7:00 pm-5:55 am

2 stops25h 55m

Chicago Midway

Sat 1/9

6:00 pm-11:35 am

2 stops26h 35m

$1,504

OsakaChicago

KIX Osaka Kansai Intl - MDW Chicago Midway

KIXMDW

Osaka Kansai Intl

Tue 10/20

7:05 pm-5:50 am

2 stops24h 45m

Chicago Midway

Sat 10/24

7:45 pm-1:20 pm

2 stops27h 35m

$1,505

OsakaChicago

KIX Osaka Kansai Intl - MDW Chicago Midway

KIXMDW

Osaka Kansai Intl

Thu 12/17

2:30 pm-5:40 am

2 stops30h 10m

Chicago Midway

Fri 1/8

3:45 pm-11:35 am

2 stops28h 50m

$1,527

OsakaChicago

KIX Osaka Kansai Intl - MDW Chicago Midway

KIXMDW

Osaka Kansai Intl

Thu 12/17

2:30 pm-5:40 am

2 stops30h 10m

Chicago Midway

Sat 1/9

6:00 pm-1:20 pm

2 stops28h 20m

$1,543

Quickest round-trip

OsakaChicago

KIX Osaka Kansai Intl - MDW Chicago Midway

KIXMDW

Osaka Kansai Intl

Thu 10/22

7:05 pm-5:50 am

2 stops24h 45m

Chicago Midway

Sun 10/25

6:30 pm-11:35 am

2 stops27h 05m

$1,552

OsakaChicago

KIX Osaka Kansai Intl - MDW Chicago Midway

KIXMDW

Osaka Kansai Intl

Thu 12/17

2:30 pm-5:40 am

2 stops30h 10m

Chicago Midway

Fri 1/8

3:50 pm-1:20 pm

2 stops30h 30m

$1,567

OsakaChicago

KIX Osaka Kansai Intl - MDW Chicago Midway

KIXMDW

Osaka Kansai Intl

Thu 12/17

2:30 pm-5:40 am

2 stops30h 10m

Chicago Midway

Fri 1/8

3:45 pm-1:20 pm

2 stops30h 35m

$1,573

OsakaChicago

KIX Osaka Kansai Intl - MDW Chicago Midway

KIXMDW

Osaka Kansai Intl

Tue 10/20

9:30 am-11:43 pm

3 stops28h 13m

Chicago Midway

Sat 10/24

3:30 pm-9:55 am

2 stops28h 25m

$1,581

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

When to book flights from Osaka to Chicago Midway Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Osaka to Chicago Midway Airport according to our flight data. Find out which month and days have the cheapest flights.

Estimated round-trip price

Cheap Osaka to Chicago Midway Airport (OSA to MDW) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Osaka to Chicago Midway Airport

Best Price Found	$512
Fastest flight time	24h 45m
Direct flights	None

The best one-way flight to Chicago Midway Airport from Osaka in the past 72 hours is $512. The best round-trip flight deal from Osaka to Chicago Midway Airport found on momondo in the last 72 hours is $1,487.

The fastest flight from Osaka to Chicago Midway Airport takes 24h 45m

There are no direct flights from Osaka to Chicago Midway Airport. There are no popular flight routes from Osaka to Chicago Midway Airport.

Search flight deals

Frequently asked questions about flying from Osaka to Chicago Midway Airport

How far is Osaka to Chicago Midway by plane?
The distance between Osaka and Chicago Midway is about 6481.8 mi. A reasonable flight in good conditions will take 24h 45m.
When did momondo last update prices for flights from Osaka to Chicago Midway Airport?
Prices for flights from Osaka to Chicago Midway Airport refresh daily.
How old do you have to be to fly from Osaka to Chicago Midway Airport?
Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Osaka to Chicago Midway Airport.
What documentation or ID do you need to fly to Chicago Midway Airport?
The travel and health documents required for your trip to Chicago Midway Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago Midway Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

Frequently asked questions about flying from Osaka to Chicago Midway Airport

How do I get Price Alerts for flights from Osaka to Chicago Midway Airport?
Search flight deals from Osaka to Chicago Midway Airport. While viewing offers you’ll have the option to create a Price Alert.
How can I save money on flights from Osaka to Chicago Midway Airport with momondo?
With “Price Forecast”, learn how soon you should book your flight in advance. Down to the day of week and time of day, our information can inform you on the ideal time to book to save on your travel. Our “Price Calendar” shows you at a quick glance when to book your travel for lower rates. By setting “Price Alerts” you can monitor changes in price and target the ideal time to book. Search for your trip destination by budget amount via our “Explore” feature. Whether you’re looking for ideas for your next travel adventure or cost-cutting tips, our “Discover” content is a great place to start.
How does momondo find its flight prices?
momondo shows deals across 700+ competitors all at once. momondo is active in 30 international markets, so you can have access to a wide range of options from airlines and OTAs alike.

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Munster

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Porter

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Griffith

Saint John

Why use momondo?

Why should I use momondo to find a flight deal from Osaka to Chicago?

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Osaka to Chicago. Millions of users trust and use momondo every year so you are in good hands.

Can I find flights from Osaka to Chicago with flexible booking policies on momondo?

Yes. momondo allows you to filter the results for Osaka to Chicago flights to just show those with flexible booking policies.

How can momondo help me find flights from Osaka to Chicago?

momondo provides multiple filters to help you find the best flight to Chicago from Osaka. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

I’m not ready to book a flight from Osaka to Chicago right now. Can momondo alert me if prices change?

If you are simply researching potential flights to Chicago, momondo offers a useful price alert feature which will track prices for flights to Chicago from Osaka and alert you when they change.