Cheap flights from Chicago Midway Airport to New York from $89

The cheapest month to fly to New York LaGuardia Airport from Chicago Midway Airport is in October. Flight prices, which tend to average around $229, are often lower during this time because this is during the off-season. If you don’t want to visit New York LaGuardia Airport in October, then you should wait until January to fly from Chicago Midway Airport, when ticket prices are also cheap, with an average price of $252.

The cheapest day to depart on your flight to New York LaGuardia Airport is on a Saturday when prices can be found for as low as $219. This is often the case because there is less demand to fly during this day of the week. Flights from Chicago Midway Airport to New York LaGuardia Airport on a Monday will generally be more expensive and average around $327. Keep in mind that these prices on both days could fluctuate depending on the season and the demand.

Our data shows that the cheapest Chicago Midway Airport to New York LaGuardia Airport flights are usually those with departure times in the evening. Our users have found flights to New York LaGuardia Airport in the evening for as low as $243. Flights in the afternoon are often more expensive with an average ticket price of $266.

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

You are more likely to see cheaper flights to New York LaGuardia Airport from Chicago Midway Airport when booking weeks ahead of your departure date. In general, you can expect to find flights to New York LaGuardia Airport for around $343 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to New York LaGuardia Airport from Chicago Midway Airport for as low as $186 on momondo.

You could potentially save up to 29% on your flight if you consider stops on a Chicago Midway Airport to New York LaGuardia Airport flight.

As of May 2026, prices for Chicago Midway Airport to New York LaGuardia Airport flights are approximately 87% cheaper when compared to flights at the same time last year.

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 126 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.

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 Chicago Midway Airport and New York LaGuardia Airport is 3 per day as of May 2026. The most frequent departure time is 5:00AM, with 41% of daily flights leaving in the afternoon.

As of May 2026, there are 27 flights per week flying from Chicago Midway Airport to New York LaGuardia Airport. The most common day of the week flights depart is Mon, with 26% of flights taking off on this day.