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 | $425 |
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
Extremely poor at handling baggage. I had oversized golf bag and JAL would not recheck in Boston. Had to haul by myself to Jet Blue. Both JAL and Jet Blue claimed I had overweight bag. Had to adjust baggage several times. Will avoid JAL in future and I always avoid Jet Blue when I can. QATAR always superior.
Extremely poor at handling baggage. I had oversized golf bag and JAL would not recheck in Boston. Had to haul by myself to Jet Blue. Both JAL and Jet Blue claimed I had overweight bag. Had to adjust baggage several times. Will avoid JAL in future and I always avoid Jet Blue when I can. QATAR always superior.
JAL using the state of art A350-1000 for JFK to HND It’s a great plane to fly Very comfortable with lower cabin altitude Quieter cabin Wider seats Big tv screen Excellent service and catering
I fly to Asia twice a year for the last 15 years. I always try to fly JAL. It’s always a pleasant experience. Since TripCase shut down, this is the first time I used Kayak for live trip notifications. I was very pleased with Kayak’s quality and helpfulness of notifications. I will be using them going forward.
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.
My wife and I liked almost everything about ANA except for the economy seat space and the cold breakfast (croissant which seemed to just come out of the fridge)
Excellent service and comfortable seats. Friendly and helpful staff. No food for a 3hr flight over lunch time which was surprising (or is that a feature of domestic flights in Japan?)
When booking the flight i picked it because it said flying with ana even on our e-ticket as well but I showed up to the airport and I flew with united. I have flew with both airlines before and I prefer ana for the food quality and comfortable. So I was disappointed in that outcome and felt the food gave me minor ibs. The whole thing was missing leading with not getting what I thought I was paying for. Felt a bait and switched. Do not have confidence in using this app in the future trips
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.
Special request meals are really below average. Vegetarian options are very limited if you didn't prebook.
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
A bit rush for transit. Food and entertainment are not available
Boarding was a little difficult. The gate area at O'Hare was very small and crowded due to multiple gates in the area. Could not hear the intercom, so had to rely on signage to see when my group was boarding and the signage was blocked by passengers standing in the gate. Flight was great and we arrived in Montreal on time.
For economy, it was very good. Staff was great, they even let some of us change seats for more leg room... Put an empty seat between us which was fantastic for a 12hr flight. Onboard entertainment was excellent, I think over 200 choices of movies/tv/etc The bad was the barely/nonfunctional wifi that cost either $16.99 or 1700 miles (full flight). It was atrocious... Definitely the worst of the last 3 long haul major airlines I was on the last few months.
Smooth boarding process. Early departure, smooth flight, early arrival. The entertainment package has very good recent movie options. The flight crew were friendly and professional.
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
All was good except for the seats, not very comfy.
2.5 hour delay sitting in the plane on the tarmac, you tell me how the experience was
This flight didn't happen for me because of overbooking.
Everything was simple and easy. The lady at the gate was super friendly, I wish I had her name to share. She's a little older, dark-haired. You can tell she likes her job and would be a great influence on any young people training with her.
Crammed in like cattle waited 30 mins for late connecting flight (flight didn’t wait for me for me when I missed my connection at 2 different airports on outward journey)
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.
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