Cheap flights from New York LaGuardia Airport to Chicago from $108

The month of January is, on average, the cheapest month to fly to Chicago from New York LaGuardia Airport, with most prices found around $205. If you’re not able to fly to Chicago in January, then November is your next best option. Flight prices from New York LaGuardia Airport to Chicago during November average around $242.

The cheapest day to depart on your flight to Chicago is on a Saturday when prices can be found for as low as $323. This is often the case because there is less demand to fly during this day of the week. When flying out on a Monday, the most expensive travel day of the week, you can expect to see flight prices from New York LaGuardia Airport to Chicago for around $405.

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from New York LaGuardia Airport to Chicago during this time can be as low as $311. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $373.

Fly from New York LaGuardia to Chicago Midway 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 $281 when searching weeks out. 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 $229 on momondo.

There are 4 cabin classes 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.

No. A direct flight is the cheapest option for a flight between New York LaGuardia Airport to Chicago.

As of August 2026, prices for New York LaGuardia Airport to Chicago flights are approximately 3% more expensive when compared to flights at the same time last year.

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

United Airlines, American Airlines and Delta are the top three most popular airlines that fly to Chicago from New York LaGuardia Airport according to our data. United Airlines is the first choice among our users, with 46% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 5 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

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 156 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, United Airlines have had the least number of delays on this route over the last 12 months; with about 14% of their flights experiencing any sort of delay.

56 flights are operational daily from New York LaGuardia Airport to Chicago as of August 2026. The most popular departure time for this route is 4:00PM, with 42% of flights per day taking off at noon.

As of August 2026, there are 392 flights per week flying from New York LaGuardia Airport to Chicago. The most common day of the week flights depart is Sun, with 21% of flights taking off on this day.