Route Price Intelligence
Cheap Flights From New York City to Chicago
Live pricing benchmarks, monthly patterns, and historical lows for this route.
Typical Price
$163
Deals From
$128
Usually Costs
$128 – $195
Lowest We've Seen
$54
Based on 8,272 price pointshigh confidence
Monthly Price Guide
Jan
$128
Feb
$105
Mar
$108
Apr
$120
May
$128
Jun
$195
Jul
$157
Aug
$128
Sep
$185
Oct
$195
Nov
$195
Dec
$195
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 February, when fares average around $105. The most expensive month tends to be June at around $195. For the best deals, consider flying in February, March, April.
Cheapest Fare Found (Last 90 Days)
The lowest round-trip price available on each day we checked
Best: $5461 price checksWorst: $78