Cheap flights from New York LaGuardia Airport to Chicago from $199

If you don’t want to visit Chicago in January, then you should wait until February to fly from New York LaGuardia Airport, when ticket prices are also cheap, with an average price of $360.

Our data shows that Thursday is the least expensive day to fly to Chicago. Tickets to fly out on this day can be as low as $538. Flights from New York LaGuardia Airport to Chicago on a Monday will generally be more expensive and average around $1,998. Keep in mind that these prices on both days could fluctuate depending on the season and the demand.

Our data shows that the cheapest New York LaGuardia Airport to Chicago flights are usually those with departure times in the morning. Our users have found flights to Chicago in the morning for as low as $752. Flights in the afternoon are often more expensive, with an average ticket price of $1,886.

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

You are more likely to see cheaper flights to Chicago from New York LaGuardia Airport when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $446 when searching weeks before you fly. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from New York LaGuardia Airport for as low as $350 on momondo.

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

Historically, on average around 18% 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 151 minutes.

Generally, flights departing in the morning tend to experience fewer delays. Flights departing at night 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, United Airlines have had the fewest delays on this route over the last 12 months, with about 13% of their flights experiencing any sort of delay.

As of November 2026, there are 70 flights per day flying from New York LaGuardia Airport to Chicago. The most common time of day flights depart is 07:00, with 46% of flights taking off at midday.

The number of flights available between New York LaGuardia Airport and Chicago is 495 per week as of November 2026. The most frequent departure day is Mon, with 17% of weekly flights leaving on this day.