Route Price Intelligence
Cheap Flights From Chicago to San Juan
Live pricing benchmarks, monthly patterns, and historical lows for this route.
Typical Price
$306
Deals From
$243
Usually Costs
$243 – $457
Lowest We've Seen
$128
Based on 3,537 price pointshigh confidence
Monthly Price Guide
Jan
$457
Feb
$457
Mar
$502
Apr
$224
May
$221
Jun
$276
Jul
$300
Aug
$238
Sep
$279
Oct
$309
Nov
$409
Dec
$486
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 $221. The most expensive month tends to be March at around $502. 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: $12872 price checksWorst: $214