Route Price Intelligence
Cheap Flights From Boston to Chicago Midway
Live pricing benchmarks, monthly patterns, and historical lows for this route.
Typical Price
$219
Great Deal
Under $219
Typical Range
$219 – $315
Lowest We've Seen
$91
Based on 271 price pointshigh confidence
Monthly Price Guide
Jan
$295
Feb
$219
Mar
$219
Apr
$217
May
$190
Jun
$208
Jul
$210
Aug
$176
Sep
$176
Oct
$251
Nov
$313
Dec
$300
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 $176. The most expensive month tends to be November at around $313. For the best deals, consider flying in August, September, May.
Typical Price by Travel Month
Median round-trip fare for each month, with the typical price range, from our ongoing tracking of this route
Cheapest month: January11,076 fares analyzedTypical low: $317
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