RareNonstop · 5h
CHI to SJUPuerto Rico
San Juan
$162
usually $340
−52%
Most monthly lows $287–$340. Cheaper than every other month on record (3).
Flights · CHI → TYO
Chicago to Tokyo
Best fare, round trip
$612
−43%
below its usual $1,070
you keep $458
RareFound
- Depart
- Thu 22 Apr
- Return
- Fri 7 May
- Stay
- 15 nights
- Flight
- 2 stops · 25h
- Airline
American
Most of this route’s monthly lows fall between $1,063 and $1,372. The drop beats 91% of measured fares on the board, over 7 observed months.
Cached fare — the booking search re-prices live before you pay.
JapanTokyoNeon canyons, 3am ramen, and the world’s most polite chaos. The yen is kind to visitors right now.Best windowMar–May · Oct–NovAirportsNarita (NRT) · Haneda (HND)Every route into TokyoFare seasonality
When this route gets cheap.
Fares bottom out in April around $612 and peak in June near $1,372, 124% dearer, across the 7 months we track. The cheapest itinerary we are tracking makes 2 stops and takes about 25 hours outbound, on a 15-night trip — ticketed under American, which on a connecting fare need not operate every leg. At $612 for 10,141 km each way, that works out to about $30 per 1,000 km flown. That is well under the $44 per 1,000 km that long-haul fares on this board typically run. Across the 34 departure cities we track at a similar distance from Tokyo, this fare ranks 3rd — 5% above the $584 from Dubai. That puts it in the cheaper half of the 25 routes of similar length we watch out of Chicago, where the middle fare is $820. The best time to be in Tokyo: Mar–May · Oct–Nov.
Day-level prices for the next 4 months
Press a day to compare its fares
The median cached fare across this calendar is 5% higher than when tracking began on 8 Aug — $1,165 then versus $1,218 now, across 18 recorded snapshots. This is a calendar-level trend, so an individual deal above can be lower. The lowest single day we have seen here is $612, on 22 Apr '27.
Cached day-level data for this route is sparse — 11 of 109 days priced, from 74 tracked fares. The days below are shown as found, with no cheapest-day or below-median call.
October 2026
November 2026
Sunday 1 November: $1.1k. Compare fares from this day.2345678910111213141516171819Friday 20 November: $1.6k. Compare fares from this day.Saturday 21 November: $833. Compare fares from this day.222324252627282930
December 2026
1Wednesday 2 December: $1.1k. Compare fares from this day.345678910111213141516171819Sunday 20 December: $2.2k. Compare fares from this day.21222324Friday 25 December: $1.4k. Compare fares from this day.262728293031
January 2027
1234567Friday 8 January: $1.1k. Compare fares from this day.910111213141516171819202122232425262728293031
Cached fares · checked 15 Oct 2026
Cheapest in Apr, around $612
43% below the $1,070 typical fare
$1196Oct, above the usual price. Compare October fares.$833Nov, below the usual price. Compare November fares.$1080Dec, around the usual price. Compare December fares.$1071Jan ’27, around the usual price. Compare January fares.$1063Feb, around the usual price. Compare February fares.$612Apr, the cheapest month. Compare April fares.$1372Jun, above the usual price. Compare June fares.
CheapestBelow usualUsualAbove usualPress a month to compare its fares
Cheapest round-trip fare found each month, Chicago to Tokyo, from cached prices.
Route facts
- Airports
- O’Hare (ORD) · Midway (MDW) ↔ Narita (NRT) · Haneda (HND)
- Flight time
- ≈25 hours outbound
- Distance
- ≈10,141 km each way
- Typical price
- $1,070 round-trip (seasonal median)
- Airlines on the board
- American
- Itineraries
- Connections on current fares
- Best months to visit
- Mar–May · Oct–Nov
Good to know
CHI → TYO, answered.
Is $612 a good price for Chicago to Tokyo?
Yes — the seasonal median for this route is around $1,070 round-trip. At $612 you're 43% below that, which we rate rare for this route.
What is the cheapest month to fly from Chicago to Tokyo?
Across 7 months of cached-fare history, Apr comes out cheapest on this route. The best months to actually be in Tokyo are Mar–May · Oct–Nov — when those overlap, that's your window.
How far in advance should I book CHI → Tokyo?
We do not publish a number for this, because we cannot measure it yet. Answering it honestly means watching the same departure date on this route over many weeks as it approaches, and that archive is still filling up — so any "book N days ahead" figure here would be borrowed from somewhere else rather than measured. What we can measure is which month is cheap: across 7 months of cached fares, Apr comes out lowest on this route. Our guide Why flight prices change covers what does move a fare.
Are there nonstop flights from Chicago to Tokyo?
The current cheapest fares involve a connection, ticketed under American. We hold no nonstop fare on this route right now, which does not mean none flies — search your exact dates to see what does.
Are these prices guaranteed?
No — these are cached fares found on real searches (this one on 17 October). Airlines reprice constantly, so the booking search re-checks the live price before you pay. Fresher finds are far more likely to still be available.
Next step
Sleeping in Tokyo?
Lock the flight first — then compare stays for 22 Apr '27 – 7 May '27 · 15 nights.
Browse hotelsMissed it?
Cached fares expire. This route has a feed of its own — follow it and the next CHI → TYO drop reaches you as soon as we find it.
Follow this route’s feedKeep browsing
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