$1,329 Cheap Flights from Madrid (MAD) to Chicago (MDW)

View $1,329 flight on Fri, Sep 26, 2025Opens in a new window

Popular airlines from Adolfo Suarez Madrid-Barajas Airport (MAD) to Chicago Midway Airport (MDW)

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Cheap Flights from Madrid to Chicago (MAD-MDW)

Prices were available within the past 7 days and start at $1,329 for one-way flights and $589 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Wed, Feb 25 - Mon, Mar 2
MAD
Madrid
MDW
Chicago
$589 Roundtrip, found 4 days ago
$589
Roundtrip
found 4 days ago
Select Delta flight, departing Wed, Feb 25 from Madrid to Chicago, returning Mon, Mar 2, priced at $589 found 4 days ago
Virgin Atlantic
Wed, Feb 25 - Mon, Mar 2
MAD
Madrid
MDW
Chicago
$589 Roundtrip, found 4 days ago
$589
Roundtrip
found 4 days ago
Select Virgin Atlantic flight, departing Wed, Feb 25 from Madrid to Chicago, returning Mon, Mar 2, priced at $589 found 4 days ago
Delta
Thu, Nov 20 - Sat, Nov 29
MAD
Madrid
MDW
Chicago
$643 Roundtrip, found 2 days ago
$643
Roundtrip
found 2 days ago
Select Delta flight, departing Thu, Nov 20 from Madrid to Chicago, returning Sat, Nov 29, priced at $643 found 2 days ago
Delta
Sat, Nov 15 - Sat, Nov 29
MAD
Madrid
MDW
Chicago
$647 Roundtrip, found 3 days ago
$647
Roundtrip
found 3 days ago
Select Delta flight, departing Sat, Nov 15 from Madrid to Chicago, returning Sat, Nov 29, priced at $647 found 3 days ago
Delta
Wed, Sep 24 - Mon, Sep 29
MAD
Madrid
MDW
Chicago
$650 Roundtrip, found 6 days ago
$650
Roundtrip
found 6 days ago
Select Delta flight, departing Wed, Sep 24 from Madrid to Chicago, returning Mon, Sep 29, priced at $650 found 6 days ago
Delta
Tue, Nov 25 - Sun, Nov 30
MAD
Madrid
MDW
Chicago
$650 Roundtrip, just found
$650
Roundtrip
just found
Select Delta flight, departing Tue, Nov 25 from Madrid to Chicago, returning Sun, Nov 30, priced at $650 just found
Delta
Fri, Aug 29 - Tue, Sep 2
MAD
Madrid
MDW
Chicago
$652 Roundtrip, found 11 hours ago
$652
Roundtrip
found 11 hours ago
Select Delta flight, departing Fri, Aug 29 from Madrid to Chicago, returning Tue, Sep 2, priced at $652 found 11 hours ago
Delta
Thu, Nov 20 - Sat, Nov 29
MAD
Madrid
MDW
Chicago
$670 Roundtrip, found 2 days ago
$670
Roundtrip
found 2 days ago
Select Delta flight, departing Thu, Nov 20 from Madrid to Chicago, returning Sat, Nov 29, priced at $670 found 2 days ago
Air France
Wed, Sep 24 - Mon, Sep 29
MAD
Madrid
MDW
Chicago
$678 Roundtrip, found 6 days ago
$678
Roundtrip
found 6 days ago
Select Air France flight, departing Wed, Sep 24 from Madrid to Chicago, returning Mon, Sep 29, priced at $678 found 6 days ago
KLM
Thu, Nov 20 - Sat, Nov 29
MAD
Madrid
MDW
Chicago
$698 Roundtrip, found 2 days ago
$698
Roundtrip
found 2 days ago
Select KLM flight, departing Thu, Nov 20 from Madrid to Chicago, returning Sat, Nov 29, priced at $698 found 2 days ago

Alternative airports near Chicago

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to O'Hare Intl. ORD. Cheapest option available. Average driving time to city center is 23 minutes. Flights from $732
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $732
Flights from Madrid (MAD) to Chicago (MDW)
Origin airport
Adolfo Suárez Madrid-Barajas
Destination airport
Midway Intl.
Airlines serving
Air France, Delta, KLM, Virgin Atlantic
Roundtrip price
$589
Distance
4190 mi

Madrid to Chicago Flights

The cheapest times to fly from Madrid to Chicago

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Madrid to Chicago are during the month of February. You can find some of the cheapest flights from Madrid to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Madrid to Chicago

Sunday is one of the best days to book for cheap flights from Madrid to Chicago: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Madrid to Chicago

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Madrid to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $1,329 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Madrid to Chicago flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Madrid to Chicago airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Frequently asked questions

How much does a flight from Adolfo Suarez Madrid-Barajas Airport (MAD) to Midway Intl. Airport (MDW) cost?
Snag a cheap one-way flight from $1,329 or cheap return flight from $589 from Adolfo Suarez Madrid-Barajas Airport (MAD) to Midway Intl. Airport (MDW) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to see our cheapest flight deals on this route.
What is the cheapest month to fly from Adolfo Suarez Madrid-Barajas Airport (MAD) to Midway Intl. Airport (MDW)?
Planning your getaway for February can help you save, as it's the cheapest month for flights between MAD and MDW. You'll usually find the lowest fares during off-peak months.
What is the cheapest airline that flies from Adolfo Suarez Madrid-Barajas Airport (MAD) to Midway Intl. Airport (MDW)?
To find the cheapest airline that'll fly you from MAD to MDW, use Expedia's filter tool. Tailor your search based on your travel needs, such as preferred carriers and cabin class. You can then sort your results by "Price (lowest to highest)" to discover the cheapest flight right away.
How many flights per day from Adolfo Suarez Madrid-Barajas Airport (MAD) to Midway Intl. Airport (MDW)?
Nonstop flights from Adolfo Suarez Madrid-Barajas Airport (MAD) to Midway Intl. Airport (MDW) aren't available daily, so you'll need to take a flight with a layover. Explore your options with Expedia's filters. Enter your travel details and choose either "1 Stop" or "2+ Stops."
What day of the week has the most flights from MAD to MDW?
You'll generally find Tuesday the quietest day for flights, while Fridays tend to be the busiest.* However this can vary from season to season and during peak travel times or public holidays.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Adolfo Suarez Madrid-Barajas Airport (MAD) to Midway Intl. Airport (MDW)?
To avoid potential delays on the Adolfo Suarez Madrid-Barajas Airport (MAD) to Midway Intl. Airport (MDW) route, aim to travel before 3 PM. Later flights are 22% more likely to be canceled.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
What airports do you fly into for Chicago from Adolfo Suarez Madrid-Barajas Airport (MAD)?
Check out your flight options from Adolfo Suarez Madrid-Barajas Airport (MAD) to O'Hare Intl. Airport (ORD). This is the only airport in Chicago you can arrive at if you're taking a direct flight.
Is it cheaper to buy a plane ticket from Adolfo Suarez Madrid-Barajas Airport (MAD) to Midway Intl. Airport (MDW) last-minute?
Holding off until just before your departure to book a flight from MAD to MDW often results in higher prices. While you may come across some last-minute offers, there's no guarantee. Keep your travel schedule open for the best chance of scoring a bargain.
Is it cheaper to book a MAD to MDW flight and hotel package?
You'll typically save money by securing a MAD to MDW flight and hotel package compared to booking separately. In fact, travelers could save hundreds of dollars by bundling with Expedia. And it's simple to manage everything in one convenient place. Once you've selected your preferred flights and accommodations, consider adding extras like car rentals, activities and tours.
Can I cancel or change the date of my flight from Adolfo Suarez Madrid-Barajas Airport (MAD) to Midway Intl. Airport (MDW)?
If you booked your MAD to MDW flight within the last 24 hours, you may be able to modify or cancel it without any fees. Depending on the airline and the ticket type you purchased, additional charges may apply for changes beyond this timeframe. Airline policies and contact information can be found in your itinerary or confirmation email. Or, visit our Customer Service portal for more details.

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*Available to One Key members.