Business Class Flight Deals from Chicago to New York City from $228

When planning your flights from Chicago to New York City, keep in mind that the most expensive times to fly are typically mid-February and late April, with prices peaking around those months. The largest peak price was observed in mid-February, reaching up to about $1349, while the best time for budget travelers is early March, where prices can drop to around $81. Overall, high-season flights can range from mid-February to late April, with prices often exceeding $700, whereas the low season tends to occur from early January to mid-March, with fares dropping below $208.

If you're planning a trip from Chicago to New York City, the best time to buy your ticket is around 26 days before departure when prices hover around $177. Waiting too long can lead to steep increases, with prices soaring to about $375 or higher if booked last minute. Booking between 78 to 57 days in advance offers good prices, but be cautious if you're within 17 days of departure, as prices rise sharply and can reach 78% above the lowest fare. It's advisable to secure your ticket as soon as possible if your departure is less than 26 days away.