
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 → TLV
Best fare, round trip
$801
−20%
below its usual $1,005
you keep $204
Most of this route’s monthly lows fall between $949 and $1,065. The drop beats 55% of measured fares on the board, over 6 observed months.
Cached fare — the booking search re-prices live before you pay.
IsraelTel AvivBauhaus blocks, a beach in the middle of the city, and Jerusalem an hour away.Best windowApr–Jun · Sep–OctAirportsBen Gurion (TLV)Every route into Tel AvivFare seasonality
Fares bottom out in January around $801 and peak in May near $1,133, 41% dearer, across the 6 months we track. The cheapest itinerary we are tracking makes 2 stops and takes about 13.5 hours outbound, on a 8-night trip — ticketed under Air Canada, which on a connecting fare need not operate every leg. At $801 for 9,903 km each way, that works out to about $40 per 1,000 km flown. That is below the $44 per 1,000 km typical of long-haul fares here. Across the 17 departure cities we track at a similar distance from Tel Aviv, this fare ranks 6th — 52% above the $526 from New York. That puts it in the cheaper half of the 25 routes of similar length we watch out of Chicago, where the middle fare is $801. The best time to be in Tel Aviv: Apr–Jun · Sep–Oct.
Day-level prices for the next 4 months
Press a day to compare its fares
The median cached fare across this calendar is 1% higher than when tracking began on 8 Aug — $1,057 then versus $1,065 now, across 21 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 $616, on 16 Sep.
Cached day-level data for this route is sparse — 9 of 107 days priced, from 50 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 Jan, around $801
20% below the $1,005 typical fare
Cheapest round-trip fare found each month, Chicago to Tel Aviv, from cached prices.
Route facts
Good to know
Yes — the seasonal median for this route is around $1,005 round-trip. At $801 you're 20% below that, which we rate good for this route.
Across 6 months of cached-fare history, Jan comes out cheapest on this route. The best months to actually be in Tel Aviv are Apr–Jun · Sep–Oct — 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We do not publish a number for this, because we cannot measure it yet.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 6 months of cached fares, Jan 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 Air Canada. 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 Tel Aviv?
Lock the flight first — then compare stays for 13–21 Jan '27 · 8 nights.
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