Route Price Intelligence
Cheap Flights From Boston to Chicago Midway
Live pricing benchmarks, monthly patterns, and historical lows for this route.
Typical Price
$249
Deals From
$205
Usually Costs
$205 – $315
Lowest We've Seen
$91
Based on 8,583 price pointshigh confidence
Monthly Price Guide
Jan
$317
Feb
$377
Mar
$228
Apr
$211
May
$181
Jun
$214
Jul
$227
Aug
$230
Sep
$241
Oct
$267
Nov
$372
Dec
$346
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 $181. The most expensive month tends to be February at around $377. 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: $9190 price checksWorst: $177