Cheap flights from New York LaGuardia Airport to Chicago from £59

The cheapest month to fly to Chicago from New York LaGuardia Airport is in January. Flight prices, which tend to average around £138, are often lower during this time because this is during the off-season. If you aren’t able to travel during the month of January, then book flights to Chicago from New York LaGuardia Airport during February instead. Flights to Chicago in February, while not as cheap as those in January, still average around £184.

The cheapest day to depart on your flight to Chicago is on a Tuesday when prices can be found for as low as £121. This is often the case because there is less demand to fly during this day of the week. The most expensive day to fly to Chicago is Thursday, with ticket prices averaging around £301.

Flying to Chicago from New York LaGuardia Airport in the evening is the least expensive time of day to depart. momondo users have found prices as low as £189 when looking at flights departing in the evening. Flights at midday are often more expensive, with an average ticket price of £277.

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 £200 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 £130 on momondo.

There are 4 cabin classes available to choose from on New York LaGuardia 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 17% 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 160 minutes.

Generally, flights departing in the morning 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, United Airlines have had the fewest delays on this route over the last 12 months, with about 14% of their flights experiencing any sort of delay.

57 flights are operational daily from New York LaGuardia Airport to Chicago as of March 2026. The most popular departure time for this route is 07:00, with 43% of flights per day taking off at midday.

404 flights are operational weekly from New York LaGuardia Airport to Chicago as of March 2026. The most popular departure day for this route is Thu, with 18% of flights per week taking off on this day.