Route Price Intelligence
Cheap Flights From Boston to Chicago
Live pricing benchmarks, monthly patterns, and historical lows for this route.
Typical Price
$389
Great Deal
Under $225
Typical Range
$225 – $399
Lowest We've Seen
$147
Based on 271 price pointshigh confidence
Monthly Price Guide
Jan
$389
Feb
—
Mar
—
Apr
$594
May
$381
Jun
$389
Jul
$389
Aug
$389
Sep
$389
Oct
$364
Nov
$364
Dec
$389
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 $364. The most expensive month tends to be April at around $594. For the best deals, consider flying in October, November, May.
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: September27,024 fares analyzedTypical low: $171