Route Price Intelligence
Cheap Flights From Chicago to San Juan
Live pricing benchmarks, monthly patterns, and historical lows for this route.
Typical Price
$392
Great Deal
Under $352
Typical Range
$352 – $462
Lowest We've Seen
$128
Based on 1,084 price pointshigh confidence
Monthly Price Guide
Jan
$420
Feb
$432
Mar
$467
Apr
$458
May
—
Jun
—
Jul
$384
Aug
$298
Sep
$307
Oct
$366
Nov
$390
Dec
$488
Cheapest Average Expensive
Best Time to Fly from Chicago to San Juan
The cheapest time to fly from Chicago to San Juan is typically August, when fares average around $298. The most expensive month tends to be December at around $488. For the best deals, consider flying in August, September, October.
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: August46,921 fares analyzedTypical low: $249