Cheap flights from New York LaGuardia Airport to Chicago from £45

The cheapest month to fly to Chicago O'Hare Intl Airport from New York LaGuardia Airport is in January. Flight prices, which tend to average around £164, 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 O'Hare Intl Airport from New York LaGuardia Airport during November instead. Flights to Chicago O'Hare Intl Airport in November, while not as cheap as those in January, still average around £169.

The cheapest day to depart from New York LaGuardia Airport to Chicago O'Hare Intl Airport is on a Tuesday. Travellers who choose to depart for Chicago O'Hare Intl Airport on a Tuesday will often find tickets for as low as £123. Be sure to avoid booking your departure on a Thursday as prices are generally higher than usual. According to our data, the average ticket price to Chicago O'Hare Intl Airport on Thursday is £264.

The cheapest time of day to fly to Chicago O'Hare Intl Airport is in the morning when flights can be purchased for as low as £181. In contrast, the most expensive time of day to depart to Chicago O'Hare Intl Airport is at midday when prices are around £279.

Fly from New York LaGuardia to Chicago O'Hare Intl for the best New York LaGuardia - Chicago O'Hare Intl flight prices

You are more likely to see cheaper flights to Chicago O'Hare Intl Airport from New York LaGuardia Airport when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago O'Hare Intl Airport for around £201 when searching weeks before you fly. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago O'Hare Intl Airport from New York LaGuardia Airport for as low as £131 on momondo.

There are 4 cabin classes available to choose from on New York LaGuardia to Chicago O'Hare Intl 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 16% 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 165 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 59 flights per day flying from New York LaGuardia Airport to Chicago O'Hare Intl Airport. The most common time of day flights depart is 14:00, with 44% of flights taking off at midday.

As of March 2026, there are 419 flights per week flying from New York LaGuardia Airport to Chicago O'Hare Intl Airport. The most common day of the week flights depart is Wed, with 17% of flights taking off on this day.