Route Price Intelligence
Cheap Flights From Chicago to San Juan
Live pricing benchmarks, monthly patterns, and historical lows for this route.
Typical Price
$309
Deals From
$261
Usually Costs
$261 – $457
Lowest We've Seen
$128
Based on 927 price pointshigh confidence
Monthly Price Guide
Jan
$457
Feb
$457
Mar
$462
Apr
$227
May
$224
Jun
$286
Jul
$293
Aug
$232
Sep
$309
Oct
$309
Nov
$396
Dec
$492
Cheapest Average Expensive
Best Time to Fly from Chicago to San Juan
The cheapest time to fly from Chicago to San Juan is typically May, when fares average around $224. The most expensive month tends to be December at around $492. For the best deals, consider flying in May, April, August.
Cheapest Fare Found (Last 90 Days)
The lowest round-trip price available on each day we checked
Best: $12871 price checksWorst: $214