Route Price Intelligence
Cheap Flights From Boston to Chicago Midway
Live pricing benchmarks, monthly patterns, and historical lows for this route.
Typical Price
$223
Deals From
$199
Usually Costs
$199 – $315
Lowest We've Seen
$91
Based on 813 price pointshigh confidence
Monthly Price Guide
Jan
$315
Feb
—
Mar
—
Apr
$226
May
$192
Jun
$207
Jul
$208
Aug
$187
Sep
$205
Oct
$251
Nov
$356
Dec
$356
Cheapest Average Expensive
Best Time to Fly from Boston to Chicago Midway
The cheapest time to fly from Boston to Chicago Midway is typically August, when fares average around $187. The most expensive month tends to be December at around $356. For the best deals, consider flying in August, May, September.
Cheapest Fare Found (Last 90 Days)
The lowest round-trip price available on each day we checked
Best: $9870 price checksWorst: $177