Cheap flights from Chicago Midway Airport to New York from $123

The cheapest month to fly to New York from Chicago Midway Airport is in November. Flight prices, which tend to average around $228, are often lower during this time because this is during the off-season. The month of January is another great option to travel to New York, with average flight prices from Chicago Midway Airport averaging around $249.

The cheapest day to depart from Chicago Midway Airport to New York is on a Friday when prices can be found for as low as $282. On the other hand, Monday is the most expensive day to depart from Chicago Midway Airport because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $411.

Our most recent data shows that the best time of day to fly to New York is in the morning. Flights from Chicago Midway Airport to New York during this time can be as low as $299. Flights to New York are more costly in the afternoon, with an average ticket price of $390. Departure times in the afternoon fall within the peak daily travel times, which is why tickets can be more expensive.

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

There are 2 cabin classes available to choose from on Chicago Midway Airport to New York flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

As of September 2026, prices for Chicago Midway Airport to New York flights are approximately 227% more expensive when compared to flights at the same time last year.

Southwest and Delta are the most popular carriers operating from Chicago Midway to New York

Southwest, Frontier and Delta are the top three most popular airlines that fly to New York from Chicago Midway Airport according to our data. Southwest is the first choice among our users, with 85% of people opting to fly with this airline when traveling to New York. Keep in mind that there are 3 different airlines that fly to New York on a routine basis, so you have a few additional options to choose from.

Historically, on average around 23% of flights between Chicago and New York have experienced a delay on any given week. The average delay length over the past 12 months has been 123 minutes.

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

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

According to our data, Southwest have had the least number of delays on this route over the last 12 months; with about 23% of their flights experiencing any sort of delay.

As of September 2026, there are 1 flights per day flying from Chicago Midway Airport to New York. The most common time of day flights depart is 9:00AM, with 45% of flights taking off in the afternoon.

7 flights are operational weekly from Chicago Midway Airport to New York as of September 2026. The most popular departure day for this route is Mon, with 100% of flights per week taking off on this day.