Route Price Intelligence
Cheap Flights From Boston to Chicago
Live pricing benchmarks, monthly patterns, and historical lows for this route.
Typical Price
$187
Deals From
$165
Usually Costs
$165 – $205
Lowest We've Seen
$94
Based on 8,482 price pointshigh confidence
Monthly Price Guide
Jan
$205
Feb
$206
Mar
$191
Apr
$168
May
$167
Jun
$172
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 $167. The most expensive month tends to be February at around $206. For the best deals, consider flying in May, April, June.
Cheapest Fare Found (Last 90 Days)
The lowest round-trip price available on each day we checked
Best: $9488 price checksWorst: $309