Cheap flights from England to Chicago from $342

The month of September is, on average, the cheapest month to fly to Chicago from England, with most prices found around $577. If you’re not able to fly to Chicago in September, then February is your next best option. Flight prices from England to Chicago during February average around $580.

The cheapest day to depart on your flight to Chicago is on a Friday when prices can be found for as low as $816. This is often the case because there is less demand to fly during this day of the week. When flying out on a Monday, the most expensive travel day of the week, you can expect to see flight prices from England to Chicago for around $911.

Our most recent data shows that the best time of day to fly to Chicago is in the morning. Flights from England to Chicago during this time can be as low as $845. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $962.

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 $743 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from England for as low as $621 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.

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

British Airways, Aer Lingus and American Airlines 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 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.

As of March 2026, 47 flights take off from England and land in Chicago each day. The most common flight departure time for this route is 10:00AM, with 50% of daily flights taking off in the afternoon.

As of March 2026, there are 335 flights per week flying from England to Chicago. The most common day of the week flights depart is Mon, with 16% of flights taking off on this day.