Cheap Flights from Chicago to Madrid starting at S$ 375

We've found these cheap flights for you. You can book one-way or return flight tickets.

Round-trip
One way

Crossed out prices are calculated based on the average price of the corresponding route on Trip.com.

Cheapest time to fly from Chicago to Madrid

We monitor flight fares to help you find the best deals effortlessly

Cheapest flights

From price

9 16
16 23
23 30
Apr

30 6
6 13
13 20
20 27
May

27 4
4 11
11 18
18 25
Jun

25 1

Displayed prices are calculated based on the lowest average weekly prices of the corresponding route on Trip.com.

Frequently Asked Questions

When to buy flight tickets from Chicago (CHI) to Madrid (MAD) the cheapest?

Airlines adjust prices for flights from Chicago to Madrid based on the date and time of your booking. By analyzing data from all airlines, on Trip.com, you can find the cheapest flight prices on Tuesdays, Wednesdays, and Saturdays.
How much is a flight from Chicago (CHI) to Madrid (MAD) cost?

According to Trip.com's data, the lowest price is around S$ 1,328.
How long is a flight from Chicago (CHI) to Madrid (MAD)?

It takes about 8 hours 25 minutes to fly from Chicago (CHI) to Madrid (MAD).
What is the transportation method from the main airport to downtown in Madrid?
- The distance from Madrid Barajas Airport to downtown is about 14km, by taxi about 30 minutes.
What are the most popular airlines that fly from Chicago (CHI) to Madrid (MAD)?

Airlines with flights from Chicago (CHI) to Madrid (MAD): British Airways, Alaska Airlines, IBERIA, Finnair, Qatar Airways and American Airlines.
What's the most popular airline for direct flights from Chicago (CHI) to Madrid (MAD)?

IBERIA operates 2 direct flights from Chicago (CHI) to Madrid (MAD).
How many airports in Madrid?

There are 1 airports near Madrid: Madrid Barajas Airport.

How to find a cheap flight from Chicago to Madrid

Wait until the last minute and flight costs are often sky-high. Plan ahead, book the right way, and your savings can soar. We have loads of saving tips to help you find a cheap flight from Chicago to Madrid. Book your flights at the right time and save more.

Choose your dates flexibly and get the best deals on flights from Chicago to Madrid.

Tap 'Date' on the flight search bar to browse the calendar for Chicago to Madrid airfare over the next 6 months in 2025. If you're looking to fly within the next 3 months, the cheapest date seems to be Tue, Apr 15, with one-way flights starting at S$ 375.

Compare cheap flight deals from hundreds of airlines for Chicago to Madrid flights.

Our extensive search lets you compare prices from over 500 airlines to find the cheapest flights from Chicago to Madrid. The cheapest flight at the moment is with American Airlines.

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Book early or wait for last-minute deals.

It's always better to book early. Flight tickets are often at their lowest when first released, usually a year ahead of departure. Keep an eye out as soon as your desired flights open for booking. If you miss the early deals, you may still find lower prices closer to your travel date.

Search for flights on the go.

For the best flight booking experience on the go, download Trip.com and search for cheap flights from Chicago to Madrid to get your exclusive deals.

Find cheapest flight ticket from Chicago to Madrid

Cheapest direct flight price	S$ 374
Cheapest return ticket price	S$ 671
Off-season for travel	February
Peak season for travel	June
Flight distance	6,732.52km
Average flight time	8 hours 25 minutes
Popular airline	Finnair