Route brief · CHI → SIN
Chicago → Singapore
$738
round-trip · too little price history on this route to compare
Jul 9 '27 – Aug 20 '27 · 42 nights
Korean Air1 stop
Cached fare — the booking search re-prices live before you pay.
Destination briefSINSingaporeA city that treats an airport as a national monument — and prices its stopover fares to tempt you.Best windowFeb–AprAirportsChangi (SIN)All routes into SingaporeWhen this route gets cheap.
Best time to be in Singapore: Feb–Apr. Fare history for this route is still thin, so we make no seasonal call yet.
The cheapest itinerary we are tracking makes one stop and takes about 20.5 hours outbound, on a 42-night trip — ticketed under Korean Air, which on a connecting fare need not operate every leg. At $738 for 15,072 km each way, that works out to about $24 per 1,000 km flown. That is well under the $40 that ultra-long-haul fares on this board typically run. Across the 14 departure cities we track at a similar distance from Singapore, this fare ranks 7th — 1.8× the $405 we hold from San Francisco. That puts it in the cheaper half of the 26 routes of similar length we watch out of Chicago, where the middle fare is $930. We have 3 months 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.
The 2 days we hold a cached fare for
Tap a date → live search
The median cached fare across this calendar is 132% higher than when tracking began on Aug 8 — $566 then versus $1,311 now, across 4 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 Aug 17.
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.
Route facts
- Airports
- O’Hare (ORD) · Midway (MDW) ↔ Changi (SIN)
- Flight time
- ~20.5 hours outbound
- Distance
- ~15,072 km each way
- Airlines on the board
- Korean Air
- Itineraries
- Connections on current fares
- Best months to visit
- Feb–Apr
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We do not publish a number for this, because we cannot measure it yet.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. See /guides/what-moves-a-flight-price/ for the levers we can measure.
Are there nonstop flights from Chicago to Singapore?
The current cheapest fares involve a connection, ticketed under Korean Air. Nonstop options exist on many dates at higher prices — check the live search for your exact dates.
Are these prices guaranteed?
No — these are cached fares found on real searches (this one on September 1). 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 Jul 9 '27 – Aug 20 '27 · 42 nights.
Browse hotels ↗
Missed 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 CHI → SIN