Cheap flights from the United Kingdom to Chicago from $366

The month of November is, on average, the cheapest month to fly to Chicago from United Kingdom, with most prices found around $582. If you’re not able to fly to Chicago in November, then September is your next best option. Flight prices from United Kingdom to Chicago during September average around $604.

The cheapest day to depart on your flight to Chicago is on a Friday when prices can be found for as low as $843. This is often the case because there is less demand to fly during this day of the week. When flying out on a Saturday, the most expensive travel day of the week, you can expect to see flight prices from United Kingdom to Chicago for around $957.

Our most recent data shows that the best time of day to fly to Chicago is at noon. Flights from United Kingdom to Chicago during this time can be as low as $874. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $955.

Fly from London Heathrow to Chicago O'Hare Intl for the best United Kingdom - Chicago flight prices

You are more likely to see cheaper flights to Chicago from United Kingdom when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $777 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from United Kingdom for as low as $639 on momondo.

JetBlue, Finnair, and Icelandair are the most popular carriers operating from United Kingdom to Chicago

British Airways, Aer Lingus and American Airlines are the top three most popular airlines that fly to Chicago from United Kingdom according to our data. British Airways is the first choice among our users, with 41% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 10 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

Historically, on average around 11% of flights between United Kingdom and Chicago have experienced a delay on any given week. The average delay length over the past 12 months has been 180 minutes.

Generally, flights departing at night tend to experience fewer delays. Flights in the evening have, in the past, seen delays more frequently in comparison.

Wednesday is statistically the day of the week which experiences the fewest number of delays on this flight route. Friday has historically seen more delays on average compared to the rest of the week.

According to our data, United Airlines have had the least number of delays on this route over the last 12 months; with about 5% of their flights experiencing any sort of delay.

As of May 2026, there are 55 flights per day flying from United Kingdom to Chicago. The most common time of day flights depart is 11:00AM, with 51% of flights taking off in the afternoon.

As of May 2026, there are 385 flights per week flying from United Kingdom to Chicago. The most common day of the week flights depart is Mon, with 14% of flights taking off on this day.