Route Price Intelligence
Cheap Flights From Chicago to San Juan
Live pricing benchmarks, monthly patterns, and historical lows for this route.
Typical Price
$366
Deals From
$276
Usually Costs
$276 – $462
Lowest We've Seen
$128
Based on 9,106 price pointshigh confidence
Monthly Price Guide
Jan
$462
Feb
$486
Mar
$380
Apr
$238
May
$251
Jun
$302
Jul
$321
Aug
$272
Sep
$457
Oct
$462
Nov
$468
Dec
$482
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 $238. The most expensive month tends to be February at around $486. For the best deals, consider flying in April, May, August.
Cheapest Fare Found (Last 90 Days)
The lowest round-trip price available on each day we checked
Best: $12890 price checksWorst: $214