Cheap flights from Chicago to New York from $52

The cheapest month to fly to New York LaGuardia Airport from Chicago is in January. Flight prices, which tend to average around $209, 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 January, then you should wait until April to fly from Chicago, when ticket prices are also cheap, with an average price of $221.

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 to New York LaGuardia Airport on a Sunday will generally be more expensive and average around $295. 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 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 $237. Flights at noon are often more expensive with an average ticket price of $271.

Fly from Chicago O'Hare Intl to New York LaGuardia for the best Chicago - New York LaGuardia flight prices

You are more likely to see cheaper flights to New York LaGuardia Airport from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to New York LaGuardia Airport for around $245 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 for as low as $189 on momondo.

There are 4 cabin classes available to choose from on Chicago to New York LaGuardia flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

You could potentially save up to 8% on your flight if you consider stops on a Chicago to New York LaGuardia Airport flight.

As of March 2026, prices for Chicago to New York LaGuardia Airport flights are approximately 70% more expensive when compared to flights at the same time last year.

United Airlines, American Airlines, and Southwest are the most popular carriers operating from Chicago to New York LaGuardia

United Airlines, American Airlines and Spirit Airlines are the top three most popular airlines that fly to New York LaGuardia Airport from Chicago according to our data. United Airlines is the first choice among our users, with 42% of people opting to fly with this airline when traveling to New York LaGuardia Airport. Keep in mind that there are 6 different airlines that fly to New York LaGuardia Airport on a routine basis, so you have a few additional options to choose from.

Historically, on average around 22% 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 143 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 20% of their flights experiencing any sort of delay.

As of March 2026, there are 67 flights per day flying from Chicago to New York LaGuardia Airport. The most common time of day flights depart is 5:00PM, with 40% of flights taking off at noon.

As of March 2026, there are 474 flights per week flying from Chicago to New York LaGuardia Airport. The most common day of the week flights depart is Mon, with 17% of flights taking off on this day.