Route Price Intelligence
Cheap Flights From Chicago to San Juan
Live pricing benchmarks, monthly patterns, and historical lows for this route.
Typical Price
$309
Great Deal
Under $257
Typical Range
$257 – $409
Lowest We've Seen
$128
Based on 271 price pointshigh confidence
Monthly Price Guide
Jan
$462
Feb
—
Mar
—
Apr
$254
May
$224
Jun
$286
Jul
$293
Aug
$232
Sep
$309
Oct
$309
Nov
$396
Dec
$477
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 $477. For the best deals, consider flying in May, August, April.
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