Route Price Intelligence
Cheap Flights From Boston to Chicago Midway
Live pricing benchmarks, monthly patterns, and historical lows for this route.
Typical Price
$220
Deals From
$197
Usually Costs
$197 – $315
Lowest We've Seen
$91
Based on 3,794 price pointshigh confidence
Monthly Price Guide
Jan
$315
Feb
—
Mar
—
Apr
$236
May
$182
Jun
$205
Jul
$207
Aug
$192
Sep
$211
Oct
$246
Nov
$356
Dec
$366
Cheapest Average Expensive
Best Time to Fly from Boston to Chicago Midway
The cheapest time to fly from Boston to Chicago Midway is typically May, when fares average around $182. The most expensive month tends to be December at around $366. For the best deals, consider flying in May, August, June.
Cheapest Fare Found (Last 90 Days)
The lowest round-trip price available on each day we checked
Best: $9874 price checksWorst: $177