Route Price Intelligence
Cheap Flights From Boston to Chicago
Live pricing benchmarks, monthly patterns, and historical lows for this route.
Typical Price
$205
Great Deal
Under $186
Typical Range
$186 – $206
Lowest We've Seen
$94
Based on 271 price pointshigh confidence
Monthly Price Guide
Jan
$205
Feb
—
Mar
—
Apr
$201
May
$173
Jun
$186
Jul
$177
Aug
$186
Sep
$205
Oct
$205
Nov
$205
Dec
$205
Cheapest Average Expensive
Best Time to Fly from Boston to Chicago
The cheapest time to fly from Boston to Chicago is typically May, when fares average around $173. The most expensive month tends to be September at around $205. For the best deals, consider flying in May, July, June.
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: September43,519 fares analyzedTypical low: $171