Cheap flights from Chicago to Madrid from $301

The month of October is, on average, the cheapest month to fly to Madrid from Chicago, with most prices found around $549. If you don’t want to visit Madrid in October, then you should wait until September to fly from Chicago, when ticket prices are also cheap, with an average price of $557.

The cheapest day to depart on your flight to Madrid is on a Wednesday when prices can be found for as low as $747. This is often the case because there is less demand to fly during this day of the week. Be sure to avoid booking your departure on a Saturday as prices are generally higher than usual. According to our data, the average ticket price to Madrid on Saturday is $899.

Flying to Madrid from Chicago in the evening is the least expensive time of day to depart. momondo users have found prices as low as $794 when looking at flights departing in the evening. Flights to Madrid are more costly in the afternoon, with an average ticket price of $805. Departure times in the afternoon fall within the peak daily travel times, which is why tickets can be more expensive.

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

You are more likely to see cheaper flights to Madrid from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to Madrid for around $691 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Madrid from Chicago for as low as $572 on momondo.

There are 3 cabin classes available to choose from on Chicago to Madrid Barajas 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 79% on your flight if you consider stops on a Chicago to Madrid flight.

As of March 2026, prices for Chicago to Madrid flights are approximately 15% cheaper when compared to flights at the same time last year.

United Airlines, Delta, and ITA Airways are the most popular carriers operating from Chicago to Madrid Barajas

Iberia, Finnair and TAP AIR PORTUGAL are the top three most popular airlines that fly to Madrid from Chicago according to our data. Iberia is the first choice among our users, with 43% of people opting to fly with this airline when traveling to Madrid. Keep in mind that there are 17 different airlines that fly to Madrid on a routine basis, so you have a few additional options to choose from.

Historically, on average around 33% of flights between Chicago and Madrid have experienced a delay on any given week. The average delay length over the past 12 months has been 153 minutes.

Generally, flights departing at night tend to experience fewer delays. Flights in the evening have, in the past, seen delays more frequently in comparison.

Saturday is statistically the day of the week which experiences the fewest number of delays on this flight route. Thursday 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 25% of their flights experiencing any sort of delay.

Lisbon (LIS) was the most common stop: 56% of momondo users choosing 1-stop flights on this route connected there.

Flights via Boston (BOS) offer the lowest average round-trip price of $302.

Flights connecting via Washington, D.C. (IAD) have the shortest average one-way travel time: 10h 26m.

Rome (FCO) has the shortest average layover time for this route: 0h 55m.

As of March 2026, there are 9 flights per day flying from Chicago to Madrid. The most common time of day flights depart is 6:00PM, with 100% of flights taking off in the evening.

As of March 2026, there are 65 flights per week flying from Chicago to Madrid. The most common day of the week flights depart is Mon, with 15% of flights taking off on this day.