Route Price Intelligence
Cheap Flights From Madison to Chicago
Live pricing benchmarks, monthly patterns, and historical lows for this route.
Typical Price
$289
Great Deal
Under $289
Typical Range
$289 – $289
Lowest We've Seen
$179
Based on 271 price pointshigh confidence
Monthly Price Guide
Jan
$289
Feb
$289
Mar
$289
Apr
$289
May
$289
Jun
$289
Jul
—
Aug
—
Sep
—
Oct
$304
Nov
$289
Dec
$289
Cheapest Average Expensive
Best Time to Fly from Madison to Chicago
The cheapest time to fly from Madison to Chicago is typically November, when fares average around $289. The most expensive month tends to be October at around $304. For the best deals, consider flying in November, December, January.
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: October7,482 fares analyzedTypical low: $209