Cheap flights from Chicago to New York from £63

If you don’t want to visit New York LaGuardia Airport in November, then you should wait until October to fly from Chicago, when ticket prices are also cheap, with an average price of £166.

On average, the least expensive day to fly to New York LaGuardia Airport from Chicago is on a Wednesday. momondo users have found tickets for Wednesday departures for as low as £132. However, this price may fluctuate depending on the airline, the season, and holidays. If your travel schedule is flexible, try to avoid departing on a Monday because tickets tend to average around £268. These prices are subject to change though, so be sure to set up a Price Alert for flights to New York LaGuardia Airport.

Our data shows that the cheapest Chicago to New York LaGuardia Airport flights are usually those with departure times at midday. Our users have found flights to New York LaGuardia Airport at midday for as low as £132. Flights to New York LaGuardia Airport are more costly in the afternoon, with an average ticket price of £188. Departure times in the afternoon fall within the peak daily travel times, which is why tickets can be more expensive.

Fly from Chicago Midway to New York LaGuardia for the best Chicago - New York LaGuardia flight prices

You are more likely to see cheaper flights to New York LaGuardia Airport from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to New York LaGuardia Airport for around £187 when searching weeks before you fly. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to New York LaGuardia Airport from Chicago for as low as £140 on momondo.

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

As of May 2026, prices for Chicago to New York LaGuardia Airport flights are approximately 22% more expensive when compared to flights at the same time last year.

Historically, on average around 23% of flights between Chicago and New York have experienced a delay on any given week. The average delay length over the past 12 months has been 143 minutes.

Generally, flights departing at night 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, Southwest have had the fewest delays on this route over the last 12 months, with about 22% of their flights experiencing any sort of delay.

As of May 2026, there are 54 flights per day flying from Chicago to New York LaGuardia Airport. The most common time of day flights depart is 08:00, with 44% of flights taking off at midday.

The number of flights available between Chicago and New York LaGuardia Airport is 380 per week as of May 2026. The most frequent departure day is Thu, with 19% of weekly flights leaving on this day.