Route Price Intelligence
Cheap Flights From Chicago to DSS
Live pricing benchmarks, monthly patterns, and historical lows for this route.
Typical Price
$2,081
Great Deal
Under $1,977
Typical Range
$1,977 – $2,255
Lowest We've Seen
$1,887
Based on 271 price pointshigh confidence
Monthly Price Guide
Jan
$2,006
Feb
$1,968
Mar
$1,982
Apr
$2,010
May
$2,118
Jun
$2,256
Jul
$2,240
Aug
—
Sep
—
Oct
—
Nov
$1,957
Dec
$2,382
Cheapest Average Expensive
Best Time to Fly from Chicago to DSS
The cheapest time to fly from Chicago to DSS is typically November, when fares average around $1,957. The most expensive month tends to be December at around $2,382. For the best deals, consider flying in November, February, March.
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