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 → KIX
Chicago to Osaka
Best fare, round trip
$1,231
Too little price history on this route to compare — the fare is shown as found.
Found
- Depart
- Wed 21 Oct
- Return
- Sun 1 Nov
- Stay
- 11 nights
- Flight
- 2 stops · 18.5h
- Airline
Alaska Airlines
Cached fare — the booking search re-prices live before you pay.
JapanOsakaJapan with the volume up — street food, blunt humour, and Kyoto and Nara both under an hour by train.Best windowMar–May · Oct–NovAirportsKansai (KIX) · Itami (ITM)Every route into OsakaFare seasonality
When this route gets cheap.
The cheapest itinerary we are tracking makes 2 stops and takes about 18.5 hours outbound, on a 11-night trip — ticketed under Alaska Airlines, which on a connecting fare need not operate every leg. At $1,231 for 10,470 km each way, that works out to about $59 per 1,000 km flown. That is above the $44 per 1,000 km typical of long-haul fares here. Across the 28 departure cities we track at a similar distance from Osaka, this fare ranks 24th — 2.1× the $582 we hold from Brussels. For context, the middle fare among the 25 routes of similar length we watch out of Chicago is $850. We have 1 month of cached prices for this route so far — not enough to call a fare cheap or expensive, so we publish the price without a percentage. Fare history here is still too short to name a cheap season. The best time to be in Osaka: Mar–May · Oct–Nov.
The one day we hold a cached fare for
Press a date to compare its fares
The median cached fare across this calendar is 7% lower than when tracking began on 9 Aug — $1,321 then versus $1,231 now, across 3 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 $1,150, on 24 Oct.
These are the only days we have a cached price for on this route so far — not the only days it flies. The search above covers any date.
Cached fares · checked 06 Oct 2026
We are still collecting this route's months — 1 month of cached prices so far, too few to chart.
Route facts
- Airports
- O’Hare (ORD) · Midway (MDW) ↔ Kansai (KIX) · Itami (ITM)
- Flight time
- ≈18.5 hours outbound
- Distance
- ≈10,470 km each way
- Airlines on the board
- Alaska Airlines
- Itineraries
- Connections on current fares
- Best months to visit
- Mar–May · Oct–Nov
Good to know
CHI → KIX, answered.
How far in advance should I book CHI → Osaka?
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. Our guide Why flight prices change covers the levers we can measure.
Are there nonstop flights from Chicago to Osaka?
The current cheapest fares involve a connection, ticketed under Alaska Airlines. 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 7 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 Osaka?
Lock the flight first — then compare stays for 21 Oct – 1 Nov · 11 nights.
Browse hotelsMissed it?
Cached fares expire. This route has a feed of its own — follow it and the next CHI → KIX drop reaches you as soon as we find it.
Follow this route’s feedKeep browsing
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