Rare1 stop · 3.5h
CHI to DFWUnited States
Dallas
$145
usually $285
−49%
Most monthly lows $223–$285. Cheaper than every other month on record (3).
Flights · CHI → SJU
Chicago to San Juan
Best fare, round trip
$162
−52%
below its usual $340
you keep $178
RareFound
- Depart
- Mon 18 Jan
- Return
- Mon 25 Jan
- Stay
- 7 nights
- Flight
- Nonstop · 5h
- Airline
Frontier Airlines
Most of this route’s monthly lows fall between $287 and $340. The drop beats 96% of measured fares on the board, over 4 observed months.
Cached fare — the booking search re-prices live before you pay.
Puerto RicoSan JuanFive centuries of old town on a Caribbean island that takes US dollars and needs no passport from the States.Best windowDec–AprAirportsLuis Muñoz Marín (SJU)Every route into San JuanFare seasonality
When this route gets cheap.
Fares bottom out in January around $162 and peak in December near $382, 136% dearer, across the 4 months we track. The cheapest itinerary we are tracking flies Frontier Airlines nonstop and takes about 5 hours outbound, on a 7-night trip. At $162 for 3,305 km each way, that works out to about $25 per 1,000 km flown. That is well under the $43 per 1,000 km that medium-haul fares on this board typically run. Of the 8 departure cities we track at a similar distance from San Juan, this is the cheapest right now — 14% under the next one, Washington. It is also the cheapest of the 7 routes of similar length we watch out of Chicago. The best time to be in San Juan: Dec–Apr.
The 8 days we hold a cached fare for
Press a date to compare its fares
The median cached fare across this calendar is 17% higher than when tracking began on 8 Aug — $296 then versus $346 now, across 20 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 $144, on 23 Oct.
- Fri 6 Nov$346
- Fri 20 Nov$338
- Fri 27 Nov$381
- Sun 3 Jan$409
- Fri 15 Jan$444
- Sun 17 Jan$248
- Mon 18 Jan$162lowest
- Wed 20 Jan$207
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 15 Oct 2026
Cheapest in Jan, around $162
52% below the $340 typical fare
$338Nov, around the usual price. Compare November fares.$382Dec, above the usual price. Compare December fares.$162Jan ’27, the cheapest month. Compare January fares.$287Apr, below the usual price. Compare April fares.
CheapestBelow usualUsualAbove usualPress a month to compare its fares
Cheapest round-trip fare found each month, Chicago to San Juan, from cached prices.
Route facts
- Airports
- O’Hare (ORD) · Midway (MDW) ↔ Luis Muñoz Marín (SJU)
- Flight time
- ≈5 hours outbound
- Distance
- ≈3,305 km each way
- Typical price
- $340 round-trip (seasonal median)
- Airlines on the board
- Frontier Airlines
- Itineraries
- Nonstop available
- Best months to visit
- Dec–Apr
Good to know
CHI → SJU, answered.
Is $162 a good price for Chicago to San Juan?
Yes — the seasonal median for this route is around $340 round-trip. At $162 you're 52% below that, which we rate rare for this route.
What is the cheapest month to fly from Chicago to San Juan?
Across 4 months of cached-fare history, Jan comes out cheapest on this route. The best months to actually be in San Juan are Dec–Apr — when those overlap, that's your window.
How far in advance should I book CHI → San Juan?
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, Jan comes out lowest on this route. Our guide Why flight prices change covers what does move a fare.
Are there nonstop flights from Chicago to San Juan?
Yes — the current board includes nonstop fares (Frontier Airlines). The outbound leg runs around 5 hours.
Are these prices guaranteed?
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 San Juan?
Lock the flight first — then compare stays for 18–25 Jan '27 · 7 nights.
Browse hotelsMissed it?
Cached fares expire. This route has a feed of its own — follow it and the next CHI → SJU drop reaches you as soon as we find it.
Follow this route’s feedKeep browsing
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