Route Price Intelligence
Cheap Flights From Boston to Chicago Midway
Live pricing benchmarks, monthly patterns, and historical lows for this route.
Typical Price
$257
Deals From
$221
Usually Costs
$221 – $301
Lowest We've Seen
$91
Based on 8,244 price pointshigh confidence
Monthly Price Guide
Jan
$147
Feb
$157
Mar
$187
Apr
$189
May
$228
Jun
$281
Jul
$268
Aug
$248
Sep
$258
Oct
$406
Nov
$381
Dec
$362
Cheapest Average Expensive
Best Time to Fly from Boston to Chicago Midway
The cheapest time to fly from Boston to Chicago Midway is typically January, when fares average around $147. The most expensive month tends to be October at around $406. For the best deals, consider flying in January, February, March.
Cheapest Fare Found (Last 90 Days)
The lowest round-trip price available on each day we checked
Best: $9179 price checksWorst: $318