Route Price Intelligence
Cheap Flights From Boston to Chicago
Live pricing benchmarks, monthly patterns, and historical lows for this route.
Typical Price
$205
Deals From
$177
Usually Costs
$177 – $207
Lowest We've Seen
$94
Based on 8,422 price pointshigh confidence
Monthly Price Guide
Jan
$205
Feb
$205
Mar
$205
Apr
$181
May
$172
Jun
$177
Jul
$177
Aug
$177
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 $172. The most expensive month tends to be September at around $205. For the best deals, consider flying in May, June, July.
Cheapest Fare Found (Last 90 Days)
The lowest round-trip price available on each day we checked
Best: $9490 price checksWorst: $160