Cheap flights from Madrid to Chicago from $445

The month of February is, on average, the cheapest month to fly to Chicago from Madrid, with most prices found around $587. If you’re not able to fly to Chicago in February, then November is your next best option. Flight prices from Madrid to Chicago during November average around $642.

The cheapest day to depart on your flight to Chicago is on a Thursday when prices can be found for as low as $652. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Madrid to Chicago for around $938.

Our most recent data shows that the best time of day to fly to Chicago is in the afternoon. Flights from Madrid to Chicago during this time can be as low as $759. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $837.

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 $772 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Madrid for as low as $663 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 12% on your flight if you consider stops on a Madrid to Chicago flight.

As of September 2026, prices for Madrid to Chicago flights are approximately 12% more expensive when compared to flights at the same time last year.

Delta and TAP AIR PORTUGAL are the most popular carriers operating from Madrid Barajas to Chicago

Iberia, Finnair and TAP AIR PORTUGAL are the top three most popular airlines that fly to Chicago from Madrid according to our data. Iberia is the first choice among our users, with 55% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 3 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

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 172 minutes.

Generally, flights departing in the morning tend to experience fewer delays. Flights in the early afternoon have, in the past, seen delays more frequently in comparison.

Wednesday is statistically the day of the week which experiences the fewest number of 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 least number of delays on this route over the last 12 months; with about 11% of their flights experiencing any sort of delay.

Lisbon (LIS) was the most common stop: 43% of momondo users choosing 1-stop flights on this route connected there.

Flights via Rome (FCO) offer the lowest average round-trip price of $590.

Flights connecting via Paris (CDG) have the shortest average one-way travel time: 12h 10m.

Paris (CDG) has the shortest average layover time for this route: 1h 03m.

As of September 2026, there are 10 flights per day flying from Madrid to Chicago. The most common time of day flights depart is 11:00AM, with 60% of flights taking off at noon.

70 flights are operational weekly from Madrid to Chicago as of September 2026. The most popular departure day for this route is Mon, with 14% of flights per week taking off on this day.