Route Price Intelligence
Cheap Flights From Boston to Chicago
Live pricing benchmarks, monthly patterns, and historical lows for this route.
Typical Price
$280
Great Deal
Under $250
Typical Range
$250 – $295
Lowest We've Seen
$94
Based on 542 price pointshigh confidence
Monthly Price Guide
Jan
$267
Feb
$294
Mar
$280
Apr
$280
May
$280
Jun
$280
Jul
$280
Aug
—
Sep
$280
Oct
$233
Nov
$264
Dec
$265
Cheapest Average Expensive
Best Time to Fly from Boston to Chicago
The cheapest time to fly from Boston to Chicago is typically October, when fares average around $233. The most expensive month tends to be February at around $294. For the best deals, consider flying in October, November, December.
Typical Price by Travel Month
Median round-trip fare for each month, with the typical price range, from our ongoing tracking of this route
Cheapest month: November11,370 fares analyzedTypical low: $205
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