Cheap flights from Chicago to New York from $104

The month of November is, on average, the cheapest month to fly to New York LaGuardia Airport from Chicago, with most prices found around $285. The month of October is another great option to travel to New York LaGuardia Airport, with average flight prices from Chicago averaging around $312.

On average, the least expensive day to fly to New York LaGuardia Airport from Chicago is on a Thursday. momondo users have found tickets for Thursday departures for as low as $117. However, this price may fluctuate depending on the airline, the season, and holidays. Flights from Chicago to New York LaGuardia Airport on a Monday will generally be more expensive and average around $414. Keep in mind that these prices on both days could fluctuate depending on the season and the demand.

According to our data, the cheapest time of day to fly to New York LaGuardia Airport is in the morning. momondo users have found flights departing from Chicago to New York LaGuardia Airport in the morning for as low as $247. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. In contrast, the most expensive time of day to depart to New York LaGuardia Airport is in the afternoon when prices are around $647.

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 $352 when searching weeks before you fly. 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 $265 on momondo.

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 143 minutes.

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

Saturday is statistically the day of the week that experiences the fewest 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 fewest delays on this route over the last 12 months, with about 22% of their flights experiencing any sort of delay.

As of April 2026, 41 flights take off from Chicago and land in New York LaGuardia Airport each day. The most common flight departure time for this route is 08:00, with 44% of daily flights taking off at midday.

The number of flights available between Chicago and New York LaGuardia Airport is 293 per week as of April 2026. The most frequent departure day is Tue, with 24% of weekly flights leaving on this day.