Cheap flights from the United Kingdom to Chicago from £252

The cheapest month to fly to Chicago from United Kingdom is in September. Flight prices, which tend to average around £432, are often lower during this time because this is during the off-season. If you aren’t able to travel during the month of September, then book flights to Chicago from United Kingdom during February instead. Flights to Chicago in February, while not as cheap as those in September, still average around £435.

The cheapest day to depart on your flight to Chicago is on a Wednesday when prices can be found for as low as £639. 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 £670.

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 £643 when looking at flights departing at midday. Flights in the afternoon are often more expensive, with an average ticket price of £664.

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 £557 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 £465 on momondo.

There are 4 cabin classes available to choose from on United Kingdom to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Icelandair, United Airlines, and Lufthansa 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 48% of people opting to fly with this airline when travelling to Chicago. Keep in mind that there are 16 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

Historically, on average around 10% 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 169 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.

Thursday 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 38 per day as of March 2026. The most frequent departure time is 12:00, with 64% of daily flights leaving in the afternoon.

As of March 2026, there are 271 flights per week flying from United Kingdom to Chicago. The most common day of the week flights depart is Sun, with 16% of flights taking off on this day.