Cheap flights from New York LaGuardia Airport to Chicago from €91

The cheapest month to fly to Chicago from New York LaGuardia Airport is in January. Flight prices, which tend to average around €180, are often lower during this time because this is during the off-season. If you don’t want to visit Chicago in January, then you should wait until November to fly from New York LaGuardia Airport, when ticket prices are also cheap, with an average price of €211.

On average, the least expensive day to fly to Chicago from New York LaGuardia Airport is on a Friday. momondo users have found tickets for Friday departures for as low as €134. However, this price may fluctuate depending on the airline, the season, and holidays. Be sure to avoid booking your departure on a Sunday as prices are generally higher than usual. According to our data, the average ticket price to Chicago on Sunday is €493.

At midday 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 €283. Flying to Chicago at midday is an ideal time because this is during off-peak travel hours. If you have a flexible travel schedule, then try to avoid flying in the evening when prices are €493 on average. Flights to Chicago from New York LaGuardia Airport in the evening are generally more expensive because this time of day is more convenient for travellers’ schedules.

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 €245 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 €202 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 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 have had the fewest delays on this route over the last 12 months, with about 14% of their flights experiencing any sort of delay.

As of July 2026, there are 66 flights per day flying from New York LaGuardia Airport to Chicago. The most common time of day flights depart is 08:00, with 45% of flights taking off at midday.

As of July 2026, 465 flights take off from New York LaGuardia Airport and land in Chicago each week. The most common flight departure day for this route is Wed, with 17% of weekly flights taking off on this day.