Cheap flights from Osaka to Chicago

Compare Osaka to Chicago flight deals

Find the cheapest month or even day of the year to fly to Chicago

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Flight deals from Osaka to Chicago

Looking for a cheap last-minute deal or the best return flight from Osaka to Chicago? If you want to travel next month, return fares start from $1,034. Find the lowest prices on one-way and return tickets right here.

Find the cheapest month to fly from Osaka to Chicago

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Osaka to Chicago flights are currently cheapest in May.

Direct flights from Osaka to Chicago

Osaka to Chicago: Flight information

The things to know before you go.
Cheapest flight found$519
Cheapest month to flyMay
Average flight time12 hrs
Most popular airlineChina Airlines
Average flights per week3

Finding cheap flights from Osaka to Chicago: Frequently asked questions

There are 4 airports in Chicago: Chicago Midway, Chicago O'Hare International, Chicago Dupage County, and Chicago Rockford.
The best price we found for a return flight from Osaka to Chicago is $1,034. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.
12 hours is the average flight time from Osaka to Chicago.
China Airlines flies direct from Osaka to Chicago.
As of March 2026, there are 12 flights per week flying from Osaka to Chicago.
The cheapest month to fly from Osaka to Chicago is usually April.
If you're flying from Osaka, the cheapest airport near Chicago is Chicago O'Hare International – which is 25.4 km away from the centre of Chicago. We've found flights into this airport from $1,034.
After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Osaka to Chicago on Tuesday, 21 April 2026.
Yes – the average flight time is 12 hours.
We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Chicago but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.
We crunched all the numbers in our flight calendar and it looks like the cheapest time to book a flight to Chicago is around 40 days in advance, so don’t leave your flight to the last minute.
In March, the average temperature is usually around 3°C. July is typically the warmest month in Chicago, when it usually averages around 26°C. You can expect the least rain in January. The coldest month is January, with temperatures averaging -8°C. The rainiest month is August.
The cheapest airline that flies to Chicago is Jetstar Japan .

Travelling from Osaka to Chicago: what you need to know

  • Start your travel planning by considering where you'll take off for your flight from Osaka to Chicago. Kansai International Airport (KIX) and Kobe Airport (UKB) are the main airports in Osaka.

  • O'Hare International Airport (ORD) and Chicago Midway International Airport (MDW) are Chicago's primary gateways.

  • The timezone in Chicago is UTC-5, which is 14 hours behind Osaka.

  • Leave enough time to catch your Osaka to Chicago flight. As a rule of thumb, arrive two hours before international departures and an hour ahead for domestic flights.

  • During popular months such as June, it's a good idea to get to the airport well in advance. Plan to arrive two hours before a domestic departure and four hours ahead for an international flight when you travel during peak periods in general.

How to find the cheapest flights from Osaka to Chicago

  • Booking early is often the key to locking in a cheap Osaka to Chicago flight. Fares tend to rise as demand increases, so the closer you get to departure, the more you'll likely spend on your ticket.

  • The 'Whole month' tool will show you the cheapest plane tickets from Osaka to Chicago across the entire month. It's a great way to find a bargain if your travel plans aren't set in stone.

  • Cut down on the time spent looking for cheap flights from Osaka to Chicago by setting up a Price Alert. You'll get an email or push notification on the app when a lower fare pops up.

  • Tailor your flights using filters. Choose your preferred arrival and departure times, total journey duration and airlines. You can also sort your results by 'Fastest,' 'Best' or 'Cheapest' Osaka to Chicago flights.

Flying from Osaka

Kansai International Airport (KIX)

  • A stopover is the perfect opportunity to break up your trip — and maybe even visit a new city. When searching for Osaka to Chicago flights departing from Kansai International Airport, deselect the 'Direct flights only' box to see where you can stop along the way. Here are some popular options to consider:

    • Los Angeles International Airport (LAX)

    • Haneda Airport (HND)

    • San Francisco International Airport (SFO)

  • KIX is about 40 kilometres from central Osaka. If you're ride-sharing, catching a cab or driving from the centre, it'll take 45 minutes or so to get there, depending on the traffic.

  • Need a convenient place to stay before your flight from Osaka to Chicago? First Cabin Kansai Airport and Hotel Nikko Kansai Airport - 3 Mins Walk to the Airport are near Kansai International Airport. They're a particularly great choice if you have an early departure.

  • 67.95% of flights that depart Kansai International Airport reach their destination on schedule.

  • KIX is located at 1 Senshukukokita, Izumisano.

Kobe Airport (UKB)

  • Depending on traffic, you can drive to UKB from central Osaka in around 45 minutes. The airport is roughly 26 kilometres away.

  • It's your holiday, so why not extend it with an extra night away from home? Consider kicking back in one of these hotels near Kobe Airport the day before your flight from Osaka to Chicago:

  • Kobe Airport has a solid reputation for punctual service. 85% of flights leaving here land precisely when expected.

  • UKB is located at 1 Kobekuko, Chuo Ward.

Arriving in Chicago

O'Hare International Airport (ORD)

  • The distance from O'Hare International Airport (ORD) to central Chicago is approximately 26 kilometres. It'll take you about 35 minutes to get to the centre driving.

  • It usually takes 55 minutes to get there when travelling by public transport.

  • Book a hotel near ORD if you're coming in on a late flight from Osaka to Chicago. Settle into one of these options and skip the long transfer:

  • Follow your own route with an O'Hare International Airport rental car. Pick up a set of wheels from Routes Car Rentals, Dollar or Budget and chase adventure across Chicago and beyond.

  • To get the lowest price, book your vehicle from O'Hare International Airport about four weeks in advance of your Osaka to Chicago flight.

  • ORD is located at 10000 West O'Hare.

Chicago Midway International Airport (MDW)

  • Chicago Midway International Airport (MDW) is about 14 kilometres from the centre of Chicago. Once you've disembarked your flight from Osaka to Chicago, it'll take you approximately 20 minutes to get to the heart of the city in a cab or ride-share.

  • You can expect the journey to take approximately 45 minutes on public transport.

  • After your flight from Osaka to Chicago, tuck yourself in at a hotel near MDW. These are some comfortable options that'll help you get into relaxation mode:

  • Dollar, Hertz and Budget make collecting a Chicago Midway International Airport rental car easy and quick. These reliable suppliers are located around or in the terminal and will get you on your way in no time.

  • Get the lowest price by securing your ride from MDW four weeks in advance. You'll also have access to a greater range of vehicles.

  • You can find Chicago Midway International Airport at 5700 South Cicero.

Chicago Rockford International Airport (RFD)

  • Make your way into the city centre after your flight from Osaka to Chicago has touched down. Central Chicago is about 129 kilometres from Chicago Rockford International Airport (RFD) and takes roughly 1 hour 25 minutes to get to by car.

  • Public transport will take you there in roughly 4 hours 15 minutes.

  • Whether you want a zippy mini for a solo getaway or a roomy SUV to fit the family, you'll find the right Chicago Rockford International Airport rental car for your needs. Check out the range of wheels available from suppliers such as Budget, Alamo and National.

  • Rental providers sometimes offer deals on early bookings, so book your vehicle from RFD well ahead of your flight from Osaka to Chicago. A little planning can save you money.

  • Chicago Rockford International Airport is located at 2 Airport Cir.

Best time to go to Chicago

  • January is the quietest month for flights from Osaka to Chicago, while August is the busiest. Pick the ideal time to go to Chicago based on whether you want a bustling atmosphere or a more laid-back vibe.

  • Before locking in your Osaka to Chicago tickets, consider what kind of weather works for you. July is the warmest month in Chicago, with temperatures ranging from 15ºC (59ºF) to 29ºC (84ºF).

  • If you'd rather travel in cooler conditions, look for a cheap flight from Osaka to Chicago in January when temperatures average between -12ºC (10ºF) and 3ºC (37ºF).

More about Chicago

Explore more of United States

  • You've done Chicago, now it's time to explore more of United States. Journey about 451 kilometres south-east to Columbus to check off its popular sights. From Franklin Park Conservatory and Botanical Gardens to Ohio Statehouse and German Village, your itinerary will be busy.

  • Around 257 kilometres south-east of Chicago, Indianapolis is another favourite stop in United States. Start your sightseeing at The Children's Museum of Indianapolis, Indianapolis Museum of Art and Indianapolis Zoo.

Prices shown on this page are estimated lowest prices only. Found in the last 45 days.