Route Price Intelligence
Cheap Flights From New York City to Chicago
Live pricing benchmarks, monthly patterns, and historical lows for this route.
Typical Price
$207
Deals From
$177
Usually Costs
$177 – $227
Lowest We've Seen
$68
Based on 8,664 price pointshigh confidence
Monthly Price Guide
Jan
$207
Feb
$207
Mar
$203
Apr
$139
May
$167
Jun
$192
Jul
$206
Aug
$180
Sep
$207
Oct
$217
Nov
$227
Dec
$215
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 April, when fares average around $139. The most expensive month tends to be November at around $227. For the best deals, consider flying in April, May, August.
Cheapest Fare Found (Last 90 Days)
The lowest round-trip price available on each day we checked
Best: $5488 price checksWorst: $110