Cheap flights from New York LaGuardia Airport to Chicago from €50

The cheapest month to fly to Chicago from New York LaGuardia Airport is in January. Flight prices, which tend to average around €158, 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 April to fly from New York LaGuardia Airport, when ticket prices are also cheap, with an average price of €205.

On average, the least expensive day to fly to Chicago from New York LaGuardia Airport is on a Saturday. momondo users have found tickets for Saturday departures for as low as €138. However, this price may fluctuate depending on the airline, the season, and holidays. Be sure to avoid booking your departure on a Tuesday as prices are generally higher than usual. According to our data, the average ticket price to Chicago on Tuesday is €530.

In the evening 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 €118. Flying to Chicago in the evening is an ideal time because this is during off-peak travel hours. If you have a flexible travel schedule, then try to avoid flying at midday when prices are €313 on average. Flights to Chicago from New York LaGuardia Airport at midday are generally more expensive because this time of day is more convenient for travellers’ schedules.

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 €230 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 €149 on momondo.

There is only 1 cabin class 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.

As of March 2026, there are 58 flights per day flying from New York LaGuardia Airport to Chicago. The most common time of day flights depart is 14:00, with 44% of flights taking off at midday.

As of March 2026, 410 flights take off from New York LaGuardia Airport and land in Chicago each week. The most common flight departure day for this route is Mon, with 18% of weekly flights taking off on this day.