Route Price Intelligence
Cheap Flights From Chicago to San Juan
Live pricing benchmarks, monthly patterns, and historical lows for this route.
Typical Price
$333
Deals From
$257
Usually Costs
$257 – $466
Lowest We've Seen
$128
Based on 8,874 price pointshigh confidence
Monthly Price Guide
Jan
$466
Feb
$477
Mar
$365
Apr
$222
May
$243
Jun
$288
Jul
$308
Aug
$258
Sep
$457
Oct
$462
Nov
$472
Dec
$487
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 $222. The most expensive month tends to be December at around $487. 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