Route Price Intelligence
Cheap Flights From New York City to Chicago
Live pricing benchmarks, monthly patterns, and historical lows for this route.
Typical Price
$187
Deals From
$154
Usually Costs
$154 – $202
Lowest We've Seen
$68
Based on 4,836 price pointshigh confidence
Monthly Price Guide
Jan
$187
Feb
$187
Mar
$197
Apr
$179
May
$157
Jun
$157
Jul
$177
Aug
$175
Sep
$169
Oct
$187
Nov
$189
Dec
$198
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 May, when fares average around $157. The most expensive month tends to be December at around $198. For the best deals, consider flying in May, June, September.
Cheapest Fare Found (Last 90 Days)
The lowest round-trip price available on each day we checked
Best: $5477 price checksWorst: $110