Route Price Intelligence
Cheap Flights From New York City to Chicago Midway
Live pricing benchmarks, monthly patterns, and historical lows for this route.
Typical Price
$271
Deals From
$224
Usually Costs
$224 – $1,283
Lowest We've Seen
$111
Based on 8,701 price pointshigh confidence
Monthly Price Guide
Jan
$1,403
Feb
$1,403
Mar
$324
Apr
$201
May
$197
Jun
$227
Jul
$250
Aug
$238
Sep
$272
Oct
$312
Nov
$1,403
Dec
$1,443
Cheapest Average Expensive
Best Time to Fly from New York City to Chicago Midway
The cheapest time to fly from New York City to Chicago Midway is typically May, when fares average around $197. The most expensive month tends to be December at around $1,443. For the best deals, consider flying in May, April, June.
Cheapest Fare Found (Last 90 Days)
The lowest round-trip price available on each day we checked
Best: $5690 price checksWorst: $134