Cheap flights from New York to Chicago from $99

The month of December is, on average, the cheapest month to fly to Chicago Midway Airport from New York, with most prices found around $39. If you are unable to visit Chicago Midway Airport during the month of December, then departing from New York during the month February is also very affordable. Most momondo users find prices during this month for around $53.

According to our data, Tuesday is the cheapest day to fly to Chicago Midway Airport from New York. The lowest ticket price found for a Tuesday departure recently was $278. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Monday is the most expensive day to depart from New York because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $403.

Flying to Chicago Midway Airport from New York in the evening is the least expensive time of day to depart. momondo users have found prices as low as $235 when looking at flights departing in the evening. Try not to purchase tickets at noon because they tend to be around $374. Of course, these prices can vary depending on the time of year and what airport you fly to.

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

There is only 1 cabin class available to choose from on New York to Chicago Midway Airport flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

No. A direct flight is the cheapest option for a flight between New York to Chicago Midway Airport.

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

Southwest, Frontier and Delta are the top three most popular airlines that fly to Chicago Midway Airport from New York according to our data. Southwest is the first choice among our users, with 59% of people opting to fly with this airline when traveling to Chicago Midway Airport. Keep in mind that there are 4 different airlines that fly to Chicago Midway Airport on a routine basis, so you have a few additional options to choose from.

Historically, on average around 23% 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 139 minutes.

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

Saturday 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 June 2026, 4 flights take off from New York and land in Chicago Midway Airport each day. The most common flight departure time for this route is 10:00AM, with 51% of daily flights taking off at noon.

The number of flights available between New York and Chicago Midway Airport is 33 per week as of June 2026. The most frequent departure day is Mon, with 24% of weekly flights leaving on this day.