Route Price Intelligence
Cheap Flights From New York City to Chicago
Live pricing benchmarks, monthly patterns, and historical lows for this route.
Typical Price
$177
Deals From
$159
Usually Costs
$159 – $197
Lowest We've Seen
$68
Based on 271 price pointshigh confidence
Monthly Price Guide
Jan
$197
Feb
—
Mar
—
Apr
$215
May
$167
Jun
$159
Jul
$177
Aug
$177
Sep
$159
Oct
$169
Nov
$197
Dec
$197
Cheapest Average Expensive
Best Time to Fly from New York City to Chicago
The cheapest time to fly from New York City to Chicago is typically June, when fares average around $159. The most expensive month tends to be April at around $215. For the best deals, consider flying in June, 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: August66,614 fares analyzedTypical low: $153