Cheap flights from England to Chicago from £239

The cheapest month to fly to Chicago from England is in November. Flight prices, which tend to average around £471, 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 England during February instead. Flights to Chicago in February, while not as cheap as those in November, still average around £479.

The cheapest day to depart on your flight to Chicago is on a Wednesday when prices can be found for as low as £673. 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 £690.

Flying to Chicago from England at midday is the least expensive time of day to depart. momondo users have found prices as low as £662 when looking at flights departing at midday. Flights in the afternoon are often more expensive, with an average ticket price of £692.

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

You are more likely to see cheaper flights to Chicago from England when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around £612 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 England for as low as £545 on momondo.

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

JetBlue, United Airlines, and Delta are the most popular carriers operating from England to Chicago

British Airways, Aer Lingus and Icelandair are the top three most popular airlines that fly to Chicago from England 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 16 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

As of July 2026, 51 flights take off from England and land in Chicago each day. The most common flight departure time for this route is 14:00, with 52% of daily flights taking off in the afternoon.

361 flights are operational weekly from England to Chicago as of July 2026. The most popular departure day for this route is Mon, with 15% of flights per week taking off on this day.