Cheap flights from London to Chicago from €495

The cheapest month to fly to Chicago from London is in September. Flight prices, which tend to average around €493, are often lower during this time because this is during the off-season. If you don’t want to visit Chicago in September, then you should wait until November to fly from London, when ticket prices are also cheap, with an average price of €564.

In the morning is the cheapest time of day to fly from London to Chicago when you can find flight prices for as low as €529. Flying to Chicago in the morning is an ideal time because this is during off-peak travel hours. If you have a flexible travel schedule, then try to avoid flying at midday when prices are €762 on average. Flights to Chicago from London at midday are generally more expensive because this time of day is more convenient for travellers’ schedules.

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

You are more likely to see cheaper flights to Chicago from London when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around €671 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 London for as low as €550 on momondo.

There are 2 cabin classes available to choose from on London to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

As of May 2026, prices for London to Chicago flights are approximately 21% more expensive when compared to flights at the same time last year.

Historically, on average around 11% of flights between London 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.

41 flights are operational daily from London to Chicago as of May 2026. The most popular departure time for this route is 11:00, with 51% of flights per day taking off in the afternoon.

As of May 2026, 288 flights take off from London and land in Chicago each week. The most common flight departure day for this route is Mon, with 18% of weekly flights taking off on this day.