Cheap flights from New York LaGuardia Airport to Chicago from C$ 146

The month of November is another great option to travel to Chicago, with average flight prices from New York LaGuardia Airport averaging around C$ 339.

The cheapest day to depart on your flight to Chicago is on a Tuesday when prices can be found for as low as C$ 196. This is often the case because there is less demand to fly during this day of the week. If your travel schedule is flexible, try to avoid departing on a Sunday because tickets tend to average around C$ 1,139. These prices are subject to change though, so be sure to set up a Price Alert for flights to Chicago.

In the morning is the cheapest time of day to fly from New York LaGuardia Airport to Chicago when you can find flight prices for as low as C$ 475. Flying to Chicago in the morning is an ideal time because this is during off-peak travel hours. At noon is when there is more demand to fly to Chicago, so prices are often more expensive at around C$ 1,184 per ticket.

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 C$ 392 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 C$ 323 on momondo.

There are 3 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.

You could potentially save up to 53% on your flight if you consider stops on a New York LaGuardia Airport to Chicago flight.

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.

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 159 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 has had the least delays on this route over the last 12 months, with about 14% of their flights experiencing any sort of delay.

As of August 2026, 40 flights take off from New York LaGuardia Airport and land in Chicago each day. The most common flight departure time for this route is 4:00p.m., with 42% of daily flights taking off at noon.

As of August 2026, there are 285 flights per week flying from New York LaGuardia Airport to Chicago. The most common day of the week flights depart is Mon, with 26% of flights taking off on this day.