The short duration of the flight and the popularity of the route make finding cheap flights from Chicago to New York a very easy task. There are many airlines offering direct flights between the two cities and since they are all competing for the same passengers, the prices are really affordable. Even if you need to book the ticket close to the departure date you won’t pay too much for the flight.

Airport choices

Those who need to fly into New York can choose among plenty of airports. Most likely though, you’ll be arriving on JFK or La Guardia. While JFK is a major international hub for Delta Airlines, La Guardia is a focus airport for US Airways. Both JFK and La Guardia serve the metropolitan area. And it’s easy to get from the airports to the city center. Another airport serving New York City is Newark. It’s well connected to the city and can be a good alternative.

When flying out of Chicago, the first choice is, most often, O’Hare International Airport. O’Hare is the busiest airport serving Chicago. It is located just 17 miles from downtown and is the largest hub for United Airlines. Also, it’s the second largest hub for American Airlines. Chicago is also served by Midway International Airport, which is located 10 miles south of downtown. Midway serves as hub for Southwest Airlines and in some cases it might be cheaper to fly into Midway than into O’Hare.

Best airline choices

The following airlines offer direct flights from Chicago to New York:

  • United Airlines
  • Continental Airlines
  • Delta Airlines
  • American Airlines
  • US Airways
  • JetBlue Airways


Out of all the airlines listed, US Airways and JetBlue Airways seem to have the highest fares though.

Typical prices

Typically, the ticket prices for flights from Chicago to New York depend on the season. During the peak summer months (July and August), as well as during the winter holidays and National holidays, the ticket prices are always at their highest.

The shoulder season (late spring, early fall) is characterized by cheaper airfare while the low season is always the cheapest time to travel.

If you plan to fly from Chicago to New York during September, the price is $174 for a round trip ticket. Prices don’t change much if you plan to travel during the first week of October either.

Money saving tips

With so many airlines offering direct flights between the two cities, it’s recommended to start looking at discount websites such as Expedia, Hotwire, Priceline, and Travelocity, before you look at specific airlines. The airlines compete for the passengers so it’s also a good idea to look on their websites and see what offers they might have.

Generally speaking, if you fly during mid-week you’ll be able to get a cheaper ticket than if you fly during the weekends. Also, try to avoid flying during the high season (summer, winter holidays) to save some more money on airfare. The off-season months are excellent to visit New York City so that’s just one more reason not to fly when everyone else is.

Do try to book your flight in advance but make sure to stick to a 2-8 weeks period before departure. Generally, that’s when the flights are cheapest. However, due to the popularity of the route and numerous flights available, it’s not that expensive to book your flight very close to the departure date.