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One of the most popular corridors in American aviation, with lots of traffic and movement, is the Chicago (CHI) to New York (NYC) route. The flight connects America's largest commercial/logistics airport with the country's financial and cultural center. Whether you're going to New York for a business trip to Wall Street or the weekend to Broadway shows, you'll find it very convenient because there are more than 40 flights to choose from in a day. The two cities are about 740 air miles apart, and travel takes about 2-2 hours 30 minutes versus 12+ hours in your own car. Due to fierce competition on the corridor, fares fluctuate greatly depending on the way you choose to fly.

There is fierce competition among both the major airlines and budget airlines flying this route, making it a good deal for the traveler.

Seasonal variations for this route do not depend as much on weather factors and are influenced more by business travel and events, conventions, and holidays since both cities are large business hubs.
High fares continue for the first part of January because of New Year's travel returns, after which they become significantly lower as regular business travel begins. This is usually one of the cheaper months of the year.
Prices become higher because of an increase in trade shows, conventions, and corporate travel to both cities. There are some spikes in prices due to Presidents' Day and spring break.
An excellent time for bargain hunters. The demand is fairly solid, but not overly impressive, and the decent weather conditions in both cities do not lead to leisure trips driving prices up like in summertime. May is often mentioned as the cheapest month to travel this route.
Summer is the busiest time for this route with high demand related to holiday travel, sightseeing trips to New York, and ongoing business travel. The period of June-early August is the most expensive in terms of average price, with some room for saving even with early morning and overnight flights.
The fall season is considered the best time for traveling between Chicago and New York due to the combination of good weather conditions and reduced demand because of the end of vacation time in schools.
The period of November is characterized by sharp price increases in the middle of this month, which is associated with Thanksgiving. This month is one of the busiest times for traveling along this route because of numerous trips of residents of both cities to their relatives.
The most expensive month of the year. Holiday travel, company year-end meeting travel, and New Year’s Eve travel to New York cause prices to reach an annual peak, especially during the last two weeks of December.