Route Price Intelligence
Cheap Flights From Chicago to San Juan
Live pricing benchmarks, monthly patterns, and historical lows for this route.
Typical Price
$405
Great Deal
Under $201
Typical Range
$201 – $498
Lowest We've Seen
$154
Based on 271 price pointshigh confidence
Monthly Price Guide
Jan
$406
Feb
$406
Mar
$511
Apr
$702
May
—
Jun
—
Jul
$524
Aug
$401
Sep
$326
Oct
$351
Nov
$363
Dec
$574
Cheapest Average Expensive
Best Time to Fly from Chicago to San Juan
The cheapest time to fly from Chicago to San Juan is typically September, when fares average around $326. The most expensive month tends to be April at around $702. For the best deals, consider flying in September, October, November.
Typical Price by Travel Month
Median round-trip fare for each month, with the typical price range, from our ongoing tracking of this route
Cheapest month: September30,166 fares analyzedTypical low: $390