ANA's 777-300ER offers premium-heavy configurations for easier upgrades and fewer passengers.
ANA Premium Economy includes lounge access at Tokyo airports, Osaka, or Honolulu.
Planning a trip from Chicago to Tokyo? KAYAK’s data-powered insights will help you find cheap flights. Learn the best time to fly, how early to book your ticket, and other tips to secure great prices.
Low season | January |
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High season | March |
Cheapest flight | $397 |
Find which airlines fly direct from Chicago to Tokyo, which days they fly and book direct flights.
Direct departures
Chicago to Tokyo
Monday
ANA, Japan Airlines, United Airlines
ANA, Japan Airlines, +1 more
Tuesday
ANA, Japan Airlines, United Airlines
ANA, Japan Airlines, +1 more
Wednesday
ANA, Japan Airlines, United Airlines
ANA, Japan Airlines, +1 more
Thursday
ANA, Japan Airlines, United Airlines
ANA, Japan Airlines, +1 more
Friday
ANA, Japan Airlines, United Airlines
ANA, Japan Airlines, +1 more
Saturday
ANA, Japan Airlines, United Airlines
ANA, Japan Airlines, +1 more
Sunday
ANA, Japan Airlines, United Airlines
ANA, Japan Airlines, +1 more
Direct returns
Tokyo to Chicago
Monday
ANA, Japan Airlines, United Airlines
ANA, Japan Airlines, +1 more
Tuesday
ANA, Japan Airlines, United Airlines
ANA, Japan Airlines, +1 more
Wednesday
ANA, Japan Airlines, United Airlines
ANA, Japan Airlines, +1 more
Thursday
ANA, Japan Airlines, United Airlines
ANA, Japan Airlines, +1 more
Friday
ANA, Japan Airlines, United Airlines
ANA, Japan Airlines, +1 more
Saturday
ANA, Japan Airlines, United Airlines
ANA, Japan Airlines, +1 more
Sunday
ANA, Japan Airlines, United Airlines
ANA, Japan Airlines, +1 more
First experience with JAL so was okay to pretty good. 10 hour flight in premium select seat. . Seats in that category should be better than pretty good. Seat pan a little short for tall people but plenty of leg room; I think JAL in process of new planes? Also, — they could have offered a bit more water throughout flight and meals not the greatest. That said, certainly 200 percent better than a very recent AK Air International flight in similar cabin class in comfort and meals.
First experience with JAL so was okay to pretty good. 10 hour flight in premium select seat. . Seats in that category should be better than pretty good. Seat pan a little short for tall people but plenty of leg room; I think JAL in process of new planes? Also, — they could have offered a bit more water throughout flight and meals not the greatest. That said, certainly 200 percent better than a very recent AK Air International flight in similar cabin class in comfort and meals.
We ordered for non vegetarian Hindu meal but instead they served us vegetarian Hindu meal. That was also not good. It was very annoying and aggravating. Hope our return from Tokyo to jfk on March 27 same is not repeated. Caterar should understand difference between non vegetarian Hindu meal and vegetarian Hindu meal.
Checked baggage process is confusing and time consuming especially when checking oversized bags. Very slow agents didn't help.
Food was great, Entertainment was bad, movies were not current and just did not have good variety. Granted I was tired so cranky might have played into my evaluation. Overall based on cost I definitely would fly them again. I am a million mile flyer on another airline, the service on JAL really beats all airlines.
The team members are extremely attentive to make sure you have the best experience.
Was in premium economy. It is slightly better than economy, but the way the seat reclines actually makes it harder to sit (the seat slides forward and the foot rest comes up - you can lie fairly well reclined but you’ll have to sit cross legged because there is no place for your legs to stretch out. Food is basic economy. Service was great. All in all good, but may make more sense to pay more for business or save a bit and just sit in economy.
Seats in "Premium Economy" were noticeably more comfortable than those in "Economy" and worth the price. My only reservation is that the foot rest did not go higher up. If it did, it would have made the seat much more comfortable.
There were agents in Haneda that assisted us with our short layover, they actually escorted us from plane to gate! Amazing service and kindness maybe eclipsed other minor issues. I had difficulty with on line check-in and because I wasn’t able to do it we had to go to the airport without advance checking. They split my friend and I in seating arrangement twice. Food quality and coordination of entrees and side dishes was a little off. Seat comfort led me to posture where I had to lean backwards a little unnaturally, from an upright position
A great flight experience - great seats, lots of ROOM for legs & in the aisle. Great attendants! My flight cost me the same as ZipAir, the website was WAY less confusing & wonky - this will be my 1st choice for my next Japan trip. Very pleased / well cared for.
Underpricer was terrible. They wanted to charge me $150 for a seat asignment. Kayak is responsible for letting this happen. Please let me know if this is going to happen in the future. If it is i will not use kayak in the future.
This was a large plane with an upper deck. It seems like business was upstairs. If it was a US airline then I would say I sat in economy plus, but I think it was just economy. Though since ANA would not allow me to choose seats for the price it may have been plus. Lots of movies to choose from, and good service.
This was the best airline I’ve ever taken. The staff are amazing. The food was great. The pilot was phenomenal. I would highly recommend this airline.
There wasn't much entertainment for my short flight but the onboarding process was smooth and the crew provided wonderful service. The seats were also reasonably comfy. Great flight.
Cabin crew were excellent in taking care of my mom as she boarded the aircraft from her wheelchair. Did not care much for the food served.
Great airline all together - triple 7 for a short flight was a plus - lots of room
Wonderfully pleasant experience. Good meal and beverage selections. Professional air staff.
Seat width can be a bit wider. not nice that they charge extra for the window seats. online check in can be greatly improved. in other words, their online interface is bad.
Seat width can be a bit wider. not nice that they charge extra for the window seats.
Seats were comfortable with excellent legroom. Meals were also quite good. The cabin crew were excellent and very helpful. The check-in experience was also very smooth.
Seats had more space than expected. No recline, that is good.
I've stomach problems after 2 hours of flight, Iris, the flight purser not only did her best to make me feel comfortable, she went above and beyond providing pain relievers medicines and ointment. She look and found a doctor passenger on the flight to provide advise. She even report on ground staffs about my condition and provide wheelchair upon arrival. Kudos to her and Cathay Pacific!
So so, crew was overly professional and lacks human touch. Equipment is very old, especially the HKG-PVG CX366 flight. That plane along with its decor must have twenty years of history, or at least I had that impression.
Crew was great. But a bit understaffed. The business class seat, etc were dated. But comfortable. Some legs had entertainment system from a decade ago. Selections were rather poor. Food was mediocre at best. Actually poor for business class standards. I liked the lounge in Hong Kong. Showers were great. Food was nice.
Everything was fine and I have no complaints or things to note.
The economy seats are much indeed roomier. Meals needs improvement.
flight delayed 45 mins - missed connection - 1 hr layover became 8 hr layover waiting for next flight -
Fast boarding flight on time boarded plane back to front instead of stupid zone groups like US airlines do...
Baggage delayed for 2 days and still chasing for reimbursement of basis items. Very horrible customer care service.
Horrible airline. Missed my baggage and don’t want to reimburse for the basis items. Pathetic customer service
Horrible. No good food. Baggage missed to onboard and came after a day. No support to compensate the delay. Customer care cannot see the status of the complaint. No reply of the email.
I do prefer to fly United and have always had excellent service, except for bad weather. Flights are on time and staff is alway curtious and helpful
They switched out gate from terminal 1 to terminal two ten minutes before boarding. So we had to make a 20 min crazy fast walk to a different terminal. Then we boarded the plane and waited for over 40 minutes until push back. Brutal
Seats were comfortable. It’s was so cold and very uncomfortable. I paid 2000 miles for wifi service that was choppy the whole flight. Would like to be reimbursed for my miles Food was so disappointing. Three cold and terrible meals for $3000 round trip. This needs to be better.
Very good - being handicap it was very hard for me in a center aisle bulkhead seat that Zi was assigned think it was 29-G as I had a hard time opening the entertainment screen and tray table. 30-G would have maid it easier. I was assign 29-G as it was the only handicap seat without being charged even though I was handicap (disability)
My flight was scheduled for about 6:05 departure. There were 11 gate changes from 4-7pm and the flight was 3 hours delayed due to operational issues. The plane taxied around the airport for about half an hour before stopping to be de-iced. It would have been nice if we were alerted of the plan to de-ice prior to the 30 minute drive around the airport. The flight attendant was friendly, which was the only redeeming thing about this flight. As a former flight attendant for United, I was extremely disappointed.
Delays took 2hours and thirty minutes making me miss my connecting flight and make me sit in the Chicago airport for 9 hours
Had a short delay once we boarded the aircraft in Chicago, but it was fixed in no time flat then we were on our way. The pilot was able to make up the time lost and we landed 5 minute later then schedualed . Great service
Our seats were all the way in back of the plane,
The seats on this flight were almost roomy enough to be the basic amount needed for human existence. I think my favorite part of this flight was it landed at an A gate, which was the most palatial part of Sea-Tac I've ever seen - a massive improvement from the S gates.
The seats on this flight were almost roomy enough to be the basic amount needed for human existence.
The whole experience what excellent, from Anjou at the ticket counter to the attendants on the flight. Although it was an older plane, it was a very good flight. One of the best flights I have had on Air Canada!
They announced before boarding that the flight was full and there would be limited space in the overhead bins and you could check in for free. We did and after we boarded the plane found it was not full and there was plenty of space in the overhead bins. I’m not sure why they made this announcement.
Economy middle seat was so narrow that I could not sit back comfortably with passengers on either side of me. Over the 9-hour flight, with my body slightly twisted most of that time, my previously-healthy left knee became very painful, even though I got up to walk multiple times. The knee is still painful 3 weeks later. Otherwise, it was a nice flight, but I was crippled over my entire vacation.
Ok Did not like that the second leg of flight was moved earlier making it a rush to make
Dealing with Air Canada was totally miserable and as a result of their website incompetence, lack of customer support, and total non-responsiveness we could not use this flight. We have made a formal complaint to Air Canada and are waiting to hear back, but if prior experience (more than one hour waits on the telephone with no response) is any guide, we wonder if we will ever hear back at all.
Liked the size of seats. Not much food offered given length of flight.
On the short flight it was fine . The flight was smooth and crew pleasant .
it was good but would be better if there were more clear directions as to how to clear or circumvent customs in Montreal.
People were very nice and helpful. But the plane is noisy, and crowded. Seats are too small. Plane was too cold too. Air Canada app is very slow. Couldn't upgrade seats to the next section. Also surprised that basic economy seats were actually standby.
People were very nice and helpful. But the plane is noisy, and crowded. Seats are too small. Plane was too cold too.
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