
CHI to SJUPuerto Rico
San Juan
$162
usually $340
−52%
Most monthly lows $287–$340. Cheaper than every other month on record (3).
Display prices in
Flights · CHI → WAW
Best fare, round trip
$678
−1%
below its usual $685
you keep $7
Most of this route’s monthly lows fall between $685 and $687. The drop beats 0% of measured fares on the board, over 4 observed months.
Cached fare — the booking search re-prices live before you pay.
PolandWarsawRebuilt from nothing and unsentimental about it — cheap, green, and far more interesting than its reputation.Best windowMay–SepAirportsChopin (WAW) · Modlin (WMI)Every route into WarsawFare seasonality
Fares on this route stay within about $71 across the 4 months we track — season matters less here than timing the drop. The cheapest itinerary we are tracking makes one stop and takes about 11 hours outbound, on a 14-night trip — ticketed under SWISS, which on a connecting fare need not operate every leg. At $678 for 7,511 km each way, that works out to about $45 per 1,000 km flown. That is about the $44 per 1,000 km typical of long-haul fares here. Across the 14 departure cities we track at a similar distance from Warsaw, this fare ranks 6th — 1.8× the $384 we hold from New York. That puts it in the cheaper half of the 34 routes of similar length we watch out of Chicago, where the middle fare is $730. The best time to be in Warsaw: May–Sep.
Day-level prices for the next 4 months
Press a day to compare its fares
The median cached fare across this calendar is 9% higher than when tracking began on 8 Aug — $685 then versus $749 now, across 22 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 $415, on 14 Sep.
Cached day-level data for this route is sparse — 9 of 107 days priced, from 68 tracked fares. The days below are shown as found, with no cheapest-day or below-median call.
October 2026
November 2026
December 2026
January 2027
Cheapest in Feb, around $678
1% below the $685 typical fare
Cheapest round-trip fare found each month, Chicago to Warsaw, from cached prices.
Route facts
Good to know
Only slightly. The seasonal median is around $685 round-trip and this fare is 1% under it. We do not call a drop notable until 20%, so this is an ordinary price for the route rather than a reason to hurry.
Across 4 months of cached-fare history, Feb comes out cheapest on this route. The best months to actually be in Warsaw are May–Sep — when those overlap, that's your window.
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 4 months of cached fares, Feb comes out lowest on this route. Our guide Why flight prices change covers what does move a fare.
The current cheapest fares involve a connection, ticketed under SWISS. We hold no nonstop fare on this route right now, which does not mean none flies — search your exact dates to see what does.
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 Warsaw?
Lock the flight first — then compare stays for 3–17 Feb '27 · 14 nights.
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Cached fares expire. This route has a feed of its own — follow it and the next CHI → WAW drop reaches you as soon as we find it.
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