Cheap flights from England to Chicago from £285

The cheapest month to fly to Chicago from England is in February. Flight prices, which tend to average around £503, are often lower during this time because this is during the off-season. If you aren’t able to travel during the month of February, then book flights to Chicago from England during January instead. Flights to Chicago in January, while not as cheap as those in February, still average around £554.

The cheapest day to depart on your flight to Chicago is on a Wednesday when prices can be found for as low as £698. 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 £754.

Flying to Chicago from England at midday is the least expensive time of day to depart. momondo users have found prices as low as £672 when looking at flights departing at midday. Flights in the afternoon are often more expensive, with an average ticket price of £726.

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 £674 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 £607 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.

Aer Lingus, TAP AIR PORTUGAL, and Icelandair 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 41% 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.

As of October 2026, 49 flights take off from England and land in Chicago each day. The most common flight departure time for this route is 11:00, with 51% of daily flights taking off in the afternoon.

346 flights are operational weekly from England to Chicago as of October 2026. The most popular departure day for this route is Fri, with 14% of flights per week taking off on this day.