$870 Cheap Flights from Osaka (ITM) to Chicago (ORD)

You can find cheap one-way flights from $870 and cheap return flights $1,253 Osaka (ITM-Itami) to Chicago, IL (ORD-O'Hare Intl.) with Expedia. Roundtrip flights usually range from $1211 to $6685. Flight prices vary based on the month and day of the week you want to travel, as well as the airline and how far in advance you book your ticket. Filter your search on Expedia by "Price (lowest to highest)" to see the cheapest fares first, and use the Price Tracking tool to receive alerts when Osaka (ITM-Itami) to Chicago, IL (ORD-O'Hare Intl.) ticket fares go up or down.

*Typical price ranges based on flights available on Expedia in the last year. Prices include multi-airline options.

The cheapest month to fly from ITM to ORD is November when demand is low. Traveling in off-peak or shoulder months is usually a good way to secure cheap tickets, just remember to avoid flying during holidays if you're able to. Use the calendar view in your search to see which months have low fares on this route.

Enter ITM to ORD and your travel dates, then apply the 'Nonstop' filter to see only direct flights.

Japan Airlines is one of the cheapest airlines offering connecting flights from Osaka (ITM) to Chicago, IL (ORD), with round-trip tickets starting from around $3,067 with a layover in Haneda (HND). Use Expedia's search tool to compare the prices and schedules of airlines that fly this route to find the best option for your plans and budget.

*Prices based on flights available on Expedia in the last year.

To find a cheap flight from Osaka (ITM-Itami) to Chicago, IL (ORD-O'Hare Intl.), be flexible with your dates. Traveling outside of peak vacation months and booking a mid-week flight can help you save. Early morning and late night flights are often more affordable, too. Expedia allows you to compare flight times, airlines and routes all in one place to find low fares. You can also set up Price Tracking and receive alerts when fares go up or down.

The best time to fly is usually mid-week (Tuesday or Wednesday) and during early morning hours as flights tend to be cheaper, less crowded, and generally more on-time. Avoid major holidays and peak vacation seasons for smoother travel. Combining off-peak days and hours often gives the best combination of cost, comfort, and convenience.

The earliest flight from Osaka (Itami) to Chicago, IL (O'Hare Intl.) usually departs at around 7:05 AM, operated by EVA Airways. This seasonal service is available in May, giving you an early start to your travels. To compare early flights on Expedia, select the "Early Morning" and "Morning" filters in your search.

The most popular departure times for flights from Osaka (ITM-Itami) to Chicago, IL (ORD-O'Hare Intl.) are in the early afternoon, from 12pm to 3pm. About 36% of passengers prefer this time window. Airlines such as Japan Airlines and All Nippon Airways operate flights during this period. This timing is favored because it allows travelers to enjoy their morning in Osaka before heading to the airport.

Flying from ITM to ORD with a connection usually takes about 15 hours 20 minutes, traveling roughly 6,466 miles. Keep in mind that actual flight times can vary due to wind patterns, weather, and air traffic.

Business class seats are offered on the ITM to ORD route with Japan Airlines.

First class is available with Japan Airlines and All Nippon Airways.

It's easy to earn miles on a Osaka (ITM-Itami) to Chicago, IL (ORD-O'Hare Intl.) flight when you book with Expedia. Before you confirm your booking, simply select your frequent flyer program and enter your program number. As a member of One Key™, you can also earn OneKeyCash™* on top of your airline miles when you book with Expedia.

*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.

From Itami (ITM), you can fly into O'Hare Intl. (ORD) and Midway Intl. (MDW) in Chicago. Some flights may connect through major hubs like Haneda (HND), Narita Intl. (NRT), FUK (FUK) before reaching Chicago. Compare routes and airports on Expedia to find the best flight options for your travel plans.

Typically, booking a last minute flight from Osaka (ITM-Itami) to Chicago, IL (ORD-O'Hare Intl.) will be more expensive than booking in advance. As the departure date approaches, there are usually fewer seats available which can drive up the cost. However, if there's some wiggle room with your travel dates and times, you could bag a cheap last-minute fare.

Securing a Osaka (ITM-Itami) to Chicago, IL (ORD-O'Hare Intl.) Chicago Vacation Packages is usually cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your travels all in one place. Select from our extensive range of stays and then add flights, activities and car rentals to your booking. Bundle everything together, and you could save hundreds of dollars.

If you booked your Osaka (ITM-Itami) to Chicago, IL (ORD-O'Hare Intl.) flight within the last 24 hours, you may be able to modify or cancel it without any fees. Depending on the airline and the type of ticket you have, additional charges may apply for changes beyond this timeframe. Airline policies and contact information can be found in your itinerary or confirmation email. Or, head to our Customer Service portal if you'd like more information.