Cheap flights from New York LaGuardia Airport to Chicago from $88

The month of January is, on average, the cheapest month to fly to Chicago Midway Airport from New York LaGuardia Airport, with most prices found around $185. If you are unable to visit Chicago Midway Airport during the month of January, then departing from New York LaGuardia Airport during the month September is also very affordable. Most momondo users find prices during this month for around $196.

According to our data, Tuesday is the cheapest day to fly to Chicago Midway Airport from New York LaGuardia Airport. The lowest ticket price found for a Tuesday departure recently was $261. 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 LaGuardia Airport because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $396.

Flying to Chicago Midway Airport from New York LaGuardia Airport in the evening is the least expensive time of day to depart. momondo users have found prices as low as $217 when looking at flights departing in the evening. Try not to purchase tickets at noon because they tend to be around $358. 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 LaGuardia - Chicago Midway flight prices

You are more likely to see cheaper flights to Chicago Midway Airport from New York LaGuardia Airport when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago Midway Airport for around $286 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago Midway Airport from New York LaGuardia Airport for as low as $168 on momondo.

Historically, on average around 22% 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 141 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 22% of their flights experiencing any sort of delay.

The number of flights available between New York LaGuardia Airport and Chicago Midway Airport is 5 per day as of May 2026. The most frequent departure time is 7:00AM, with 50% of daily flights leaving at noon.

37 flights are operational weekly from New York LaGuardia Airport to Chicago Midway Airport as of May 2026. The most popular departure day for this route is Mon, with 19% of flights per week taking off on this day.