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 → SIN
Chicago to Singapore
Best fare, round trip
$938
Too little price history on this route to compare — the fare is shown as found.
Found
- Depart
- Tue 20 Oct
- Return
- Sat 24 Oct
- Stay
- 4 nights
- Flight
- 1 stop · 19.5h
- Airline
Cathay Pacific
Cached fare — the booking search re-prices live before you pay.
SingaporeA city that treats an airport as a national monument — and prices its stopover fares to tempt you.Best windowFeb–AprAirportsChangi (SIN)Every route into SingaporeFare seasonality
When this route gets cheap.
The cheapest itinerary we are tracking makes one stop and takes about 19.5 hours outbound, on a 4-night trip — ticketed under Cathay Pacific, which on a connecting fare need not operate every leg. At $938 for 15,072 km each way, that works out to about $31 per 1,000 km flown. That is below the $42 per 1,000 km typical of ultra-long-haul fares here. Across the 10 departure cities we track at a similar distance from Singapore, this fare ranks 5th — 1.7× the $561 we hold from Madrid. That puts it in the cheaper half of the 26 routes of similar length we watch out of Chicago, where the middle fare is $995. 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 Singapore: Feb–Apr.
The 2 days we hold a cached fare for
Press a date to compare its fares
The median cached fare across this calendar is 69% higher than when tracking began on 8 Aug — $566 then versus $956 now, across 9 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 $566, on 17 Aug.
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 13 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) ↔ Changi (SIN)
- Flight time
- ≈19.5 hours outbound
- Distance
- ≈15,072 km each way
- Airlines on the board
- Cathay Pacific
- Itineraries
- Connections on current fares
- Best months to visit
- Feb–Apr
Good to know
CHI → SIN, answered.
How far in advance should I book CHI → Singapore?
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 Singapore?
The current cheapest fares involve a connection, ticketed under Cathay Pacific. 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 15 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 Singapore?
Lock the flight first — then compare stays for 20–24 Oct · 4 nights.
Browse hotelsMissed it?
Cached fares expire. This route has a feed of its own — follow it and the next CHI → SIN drop reaches you as soon as we find it.
Follow this route’s feedKeep browsing
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