Route Price Intelligence
Cheap Flights From Boston to Chicago Midway
Live pricing benchmarks, monthly patterns, and historical lows for this route.
Typical Price
$260
Deals From
$225
Usually Costs
$225 – $315
Lowest We've Seen
$91
Based on 8,697 price pointshigh confidence
Monthly Price Guide
Jan
$335
Feb
$396
Mar
$221
Apr
$201
May
$177
Jun
$237
Jul
$252
Aug
$241
Sep
$257
Oct
$282
Nov
$396
Dec
$337
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 $177. The most expensive month tends to be February at around $396. For the best deals, consider flying in May, April, March.
Cheapest Fare Found (Last 90 Days)
The lowest round-trip price available on each day we checked
Best: $9188 price checksWorst: $318