Route Price Intelligence
Cheap Flights From Chicago to San Juan
Live pricing benchmarks, monthly patterns, and historical lows for this route.
Typical Price
$316
Deals From
$241
Usually Costs
$241 – $417
Lowest We've Seen
$128
Based on 8,536 price pointshigh confidence
Monthly Price Guide
Jan
$217
Feb
$217
Mar
$242
Apr
$202
May
$228
Jun
$309
Jul
$281
Aug
$243
Sep
$275
Oct
$390
Nov
$399
Dec
$417
Cheapest Average Expensive
Best Time to Fly from Chicago to San Juan
The cheapest time to fly from Chicago to San Juan is typically April, when fares average around $202. The most expensive month tends to be December at around $417. For the best deals, consider flying in April, January, February.
Cheapest Fare Found (Last 90 Days)
The lowest round-trip price available on each day we checked
Best: $12864 price checksWorst: $197