Cheap flights from New York to Chicago from C$ 102

The month of November is another great option to travel to Chicago, with average flight prices from New York averaging around C$ 295.

The cheapest day to depart on your flight to Chicago is on a Tuesday when prices can be found for as low as C$ 238. This is often the case because there is less demand to fly during this day of the week. If your travel schedule is flexible, try to avoid departing on a Sunday because tickets tend to average around C$ 1,101. These prices are subject to change though, so be sure to set up a Price Alert for flights to Chicago.

In the afternoon is the cheapest time of day to fly from New York to Chicago when you can find flight prices for as low as C$ 363. Flying to Chicago in the afternoon is an ideal time because this is during off-peak travel hours. At noon is when there is more demand to fly to Chicago, so prices are often more expensive at around C$ 1,076 per ticket.

Fly from Newark to Chicago Midway for the best New York - Chicago flight prices

You are more likely to see cheaper flights to Chicago from New York when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around C$ 324 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from New York for as low as C$ 220 on momondo.

You could potentially save up to 38% on your flight if you consider stops on a New York to Chicago flight.

As of May 2026, prices for New York to Chicago flights are approximately 40% more expensive when compared to flights at the same time last year.

Historically, on average around 19% of flights between New York and Chicago have experienced a delay on any given week. The average delay length over the past 12 months has been 158 minutes.

Generally, flights departing in the morning tend to experience fewer delays. Flights departing at night have, in the past, seen delays more frequently in comparison.

Saturday is statistically the day of the week that experiences the fewest delays on this flight route. Sunday has historically seen more delays on average compared to the rest of the week.

According to our data, United Airlines has had the least delays on this route over the last 12 months, with about 14% of their flights experiencing any sort of delay.

The number of flights available between New York and Chicago is 119 per day as of May 2026. The most frequent departure time is 2:00p.m., with 45% of daily flights leaving at noon.

The number of flights available between New York and Chicago is 837 per week as of May 2026. The most frequent departure day is Mon, with 17% of weekly flights leaving on this day.