Cheap flights from Tokyo to Chicago from $386

The month of September is, on average, the cheapest month to fly to Chicago from Tokyo, with most prices found around $525. If you’re not able to fly to Chicago in September, then July is your next best option. Flight prices from Tokyo to Chicago during July average around $669.

The cheapest day to depart on your flight to Chicago is on a Tuesday when prices can be found for as low as $1,371. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Tokyo to Chicago for around $1,781.

Our most recent data shows that the best time of day to fly to Chicago is in the afternoon. Flights from Tokyo to Chicago during this time can be as low as $1,479. In contrast, the most expensive time of day to depart to Chicago is in the morning when prices are around $1,799.

Fly from Tokyo Haneda to Chicago O'Hare Intl for the best Tokyo - Chicago flight prices

You could potentially save up to 50% on your flight if you consider stops on a Tokyo to Chicago flight.

Historically, on average around 14% of flights between Tokyo and Chicago have experienced a delay on any given week. The average delay length over the past 12 months has been 147 minutes.

Generally, flights departing in the morning tend to experience fewer delays. Flights in the evening have, in the past, seen delays more frequently in comparison.

Wednesday is statistically the day of the week which experiences the fewest number of delays on this flight route. Sunday has historically seen more delays on average compared to the rest of the week.

According to our data, ANA have had the least number of delays on this route over the last 12 months; with about 11% of their flights experiencing any sort of delay.

Montreal (YUL) was the most common stop: 82% of momondo users choosing 1-stop flights on this route connected there.

Flights via Taipei City (TPE) offer the lowest average round-trip price of $979.

Flights connecting via Los Angeles (LAX) have the shortest average one-way travel time: 15h 58m.

Montreal (YUL) has the shortest average layover time for this route: 1h 19m.

As of April 2026, there are 11 flights per day flying from Tokyo to Chicago. The most common time of day flights depart is 5:00PM, with 52% of flights taking off in the afternoon.

As of April 2026, there are 81 flights per week flying from Tokyo to Chicago. The most common day of the week flights depart is Mon, with 19% of flights taking off on this day.