Cheap flights from the United Kingdom to Chicago from £269

The cheapest month to fly to Chicago from United Kingdom is in November. Flight prices, which tend to average around £427, are often lower during this time because this is during the off-season. If you aren’t able to travel during the month of November, then book flights to Chicago from United Kingdom during September instead. Flights to Chicago in September, while not as cheap as those in November, still average around £443.

The cheapest day to depart on your flight to Chicago is on a Thursday when prices can be found for as low as £637. This is often the case because there is less demand to fly during this day of the week. The most expensive day to fly to Chicago is Sunday, with ticket prices averaging around £665.

Flying to Chicago from United Kingdom at midday is the least expensive time of day to depart. momondo users have found prices as low as £636 when looking at flights departing at midday. Flights in the afternoon are often more expensive, with an average ticket price of £660.

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 £570 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 United Kingdom for as low as £469 on momondo.

SWISS, Virgin Atlantic, and Delta are the most popular carriers operating from United Kingdom to Chicago

British Airways, Aer Lingus and Lufthansa 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 46% of people opting to fly with this airline when travelling to Chicago. Keep in mind that there are 17 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 departing in the evening have, in the past, seen delays more frequently in comparison.

Wednesday is statistically the day of the week that experiences the fewest 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 fewest delays on this route over the last 12 months, with about 5% of their flights experiencing any sort of delay.

The number of flights available between United Kingdom and Chicago is 55 per day as of May 2026. The most frequent departure time is 11:00, with 51% of daily flights leaving 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.