
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 → MEX
Best fare, round trip
$212
−30%
below its usual $305
you keep $93
Most of this route’s monthly lows fall between $296 and $325. The drop beats 78% of measured fares on the board, over 5 observed months.
Cached fare — the booking search re-prices live before you pay.
MexicoMexico CityAltitude, murals, and arguably the best food city in the hemisphere at street prices.Best windowMar–May · Oct–NovAirportsBenito Juárez (MEX) · Felipe Ángeles (NLU)Every route into Mexico CityFare seasonality
Fares bottom out in February around $212 and peak in October near $367, 73% dearer, across the 5 months we track. The cheapest itinerary we are tracking flies Viva Aerobus nonstop and takes about 4.5 hours outbound, on a 1-night trip. At $212 for 2,722 km each way, that works out to about $39 per 1,000 km flown. That is below the $43 per 1,000 km typical of medium-haul fares here. Of the 7 departure cities we track at a similar distance from Mexico City, this is the cheapest right now — 30% under the next one, Miami. It is also the 3rd cheapest of the 7 routes of similar length we watch out of Chicago. The best time to be in Mexico City: Mar–May · Oct–Nov.
Day-level prices for the next 4 months
Press a day to compare its fares
The median cached fare across this calendar is 8% higher than when tracking began on 8 Aug — $342 then versus $371 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 $122, on 13 Nov.
Cached day-level data for this route is sparse — 11 of 107 days priced, from 94 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 $212
30% below the $305 typical fare
Cheapest round-trip fare found each month, Chicago to Mexico City, from cached prices.
Route facts
Good to know
Yes — the seasonal median for this route is around $305 round-trip. At $212 you're 30% below that, which we rate great for this route.
Across 5 months of cached-fare history, Feb comes out cheapest on this route. The best months to actually be in Mexico City are Mar–May · Oct–Nov — 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We do not publish a number for this, because we cannot measure it yet.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 5 months of cached fares, Feb comes out lowest on this route. Our guide Why flight prices change covers what does move a fare.
Yes — the current board includes nonstop fares (Viva Aerobus). The outbound leg runs around 4.5 hours.
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 Mexico City?
Lock the flight first — then compare stays for 27–28 Feb '27 · 1 night.
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