Cheap flights from Madrid to Chicago from £340

The cheapest month to fly to Chicago from Madrid is in February. Flight prices, which tend to average around £422, 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 Madrid during November instead. Flights to Chicago in November, while not as cheap as those in February, still average around £439.

The cheapest day to depart on your flight to Chicago is on a Friday when prices can be found for as low as £564. 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 Tuesday, with ticket prices averaging around £1,024.

Fly from Madrid Barajas to Chicago O'Hare Intl for the best Madrid Barajas - Chicago flight prices

You are more likely to see cheaper flights to Chicago from Madrid when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around £576 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 Madrid for as low as £491 on momondo.

There are 3 cabin classes available to choose from on Madrid to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

You could potentially save up to 62% on your flight if you consider stops on a Madrid to Chicago flight.

Historically, on average around 15% of flights between Madrid and Chicago have experienced a delay on any given week. The average delay length over the past 12 months has been 171 minutes.

Generally, flights departing in the morning tend to experience fewer delays. Flights departing in the early afternoon 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. Sunday has historically seen more delays on average compared to the rest of the week.

According to our data, American Airlines have had the fewest delays on this route over the last 12 months, with about 11% of their flights experiencing any sort of delay.

The number of flights available between Madrid and Chicago is 8 per day as of August 2026. The most frequent departure time is 11:00, with 56% of daily flights leaving at midday.

As of August 2026, there are 60 flights per week flying from Madrid to Chicago. The most common day of the week flights depart is Mon, with 17% of flights taking off on this day.