Route Price Intelligence
Cheap Flights From Boston to Chicago
Live pricing benchmarks, monthly patterns, and historical lows for this route.
Typical Price
$152
Deals From
$141
Usually Costs
$141 – $182
Lowest We've Seen
$94
Based on 8,547 price pointshigh confidence
Monthly Price Guide
Jan
$135
Feb
$137
Mar
$137
Apr
$147
May
$147
Jun
$171
Jul
$161
Aug
$156
Sep
$135
Oct
$161
Nov
$145
Dec
$136
Cheapest Average Expensive
Best Time to Fly from Boston to Chicago
The cheapest time to fly from Boston to Chicago is typically January, when fares average around $135. The most expensive month tends to be June at around $171. For the best deals, consider flying in January, September, December.
Cheapest Fare Found (Last 90 Days)
The lowest round-trip price available on each day we checked
Best: $9462 price checksWorst: $309