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$248+ Cheap flights from Midway (MDW) to Madrid, Spain (MAD)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/5. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MAD
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
1 adult, Economy
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Cheap flight deals from Midway to Madrid

Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to Madrid (MAD). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated September 11, 2025.

Round-trip from

$438
(KLM)

One-way from

$248
(Kiwi.com)

Popular in

June

Cheapest in

February

Average price

$606
From Chicago Midway to Madrid Barajas
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One-way flight from Chicago Midway to Madrid Barajas
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Highest demand for flights based on searches. 20% potential increase in price ($183 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($26 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find flight deals from Midway to Madrid

Cheapest flights from Midway to Madrid
Explore the most affordable flight options available from Midway to Madrid. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 11, 2025.

This Delta deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/2912:43 pmMDW - MAD
1 stop13h 52mDelta
Tue 11/2511:15 amMAD - MDW
1 stop19h 17mDelta
Deal found 9/10$438
This Delta deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/36:00 amMDW - MAD
2 stops19h 00mDelta
Wed 12/1011:15 amMAD - MDW
1 stop19h 17mDelta
Deal found 9/10$443
This Delta deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/171:08 pmMDW - MAD
2 stops20h 37mDelta
Tue 9/2310:05 amMAD - MDW
1 stop18h 31mDelta
Deal found 9/10$457
This Delta deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/66:00 amMDW - MAD
1 stop20h 35mDelta
Thu 10/166:00 amMAD - MDW
2 stops19h 25mDelta
Deal found 9/8$463
This Delta deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/612:48 pmMDW - MAD
1 stop13h 47mDelta
Wed 10/156:00 amMAD - MDW
2 stops19h 25mDelta
Deal found 9/10$464
This Delta deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/36:00 amMDW - MAD
2 stops19h 00mDelta
Tue 12/96:00 amMAD - MDW
2 stops19h 00mDelta
Deal found 9/10$467
This Delta deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/261:14 pmMDW - MAD
2 stops15h 56mDelta
Fri 12/1211:15 amMAD - MDW
1 stop19h 17mDelta
Deal found 9/11$470
This Delta deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/36:23 pmMDW - MAD
2 stops13h 57mDelta
Wed 11/196:00 amMAD - MDW
2 stops19h 18mDelta
Deal found 9/11$481
This Delta deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/26:23 pmMDW - MAD
2 stops16h 17mDelta
Tue 11/116:00 amMAD - MDW
2 stops19h 18mDelta
Deal found 9/9$482

Cheapflights Fare Finder

 
Customize your flight search to find flights from Midway to Madrid that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated September 11, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Madrid that are best for you.

Fly from

Midway

Fly to

Madrid

Route

Depart

Return

Price

ChicagoMadrid

MDW - MAD

MDWMAD

Chicago Midway

Mon 10/6

6:00 am-9:35 am

1 stop20h 35m

Madrid Barajas

Thu 10/16

6:00 am-6:25 pm

2 stops19h 25m

$463

ChicagoMadrid

MDW - MAD

MDWMAD

Chicago Midway

Wed 12/3

6:00 am-8:00 am

2 stops19h 00m

Madrid Barajas

Tue 12/9

6:00 am-6:00 pm

2 stops19h 00m

$467

ChicagoMadrid

MDW - MAD

MDWMAD

Chicago Midway

Tue 11/4

1:08 pm-10:15 am

2 stops14h 07m

Madrid Barajas

Thu 11/20

11:15 am-11:32 pm

1 stop19h 17m

$470

ChicagoMadrid

MDW - MAD

MDWMAD

Chicago Midway

Sun 11/2

6:23 pm-5:40 pm

2 stops16h 17m

Madrid Barajas

Tue 11/11

6:00 am-6:18 pm

2 stops19h 18m

$483

ChicagoMadrid

MDW - MAD

MDWMAD

Chicago Midway

Mon 11/3

6:23 pm-5:40 pm

2 stops16h 17m

Madrid Barajas

Tue 11/11

6:00 am-6:08 pm

2 stops19h 08m

$483

ChicagoMadrid

MDW - MAD

MDWMAD

Chicago Midway

Sat 9/27

6:00 am-9:35 am

1 stop20h 35m

Madrid Barajas

Tue 11/25

11:15 am-11:32 pm

1 stop19h 17m

$488

ChicagoMadrid

MDW - MAD

MDWMAD

Chicago Midway

Mon 11/17

9:32 am-9:15 am

2 stops16h 43m

Madrid Barajas

Sun 11/23

10:00 am-11:32 pm

2 stops20h 32m

$492

ChicagoMadrid

MDW - MAD

MDWMAD

Chicago Midway

Wed 12/3

6:00 am-8:00 am

2 stops19h 00m

Madrid Barajas

Sun 12/7

10:00 am-9:54 am

2 stops30h 54m

$492

ChicagoMadrid

MDW - MAD

MDWMAD

Chicago Midway

Wed 11/12

1:14 pm-12:10 pm

2 stops15h 56m

Madrid Barajas

Wed 11/19

6:00 am-6:08 pm

2 stops19h 08m

$493

ChicagoMadrid

MDW - MAD

MDWMAD

Chicago Midway

Fri 11/7

6:00 am-8:00 am

2 stops19h 00m

Madrid Barajas

Fri 11/14

6:00 am-4:38 pm

2 stops17h 38m

$518

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/10

Showing 1-10 of 21 results
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Best time to book a flight from Midway to Madrid

Have a flexible travel schedule? Discover the best time to fly to Madrid from Midway with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chicago Midway Airport to Madrid

What is the cheapest time of day to fly from MDW to MAD?

Find hourly flight availability from Midway to Madrid. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 11, 2025.

A simple way to save on the total cost of your ticket is to fly from Chicago Midway Airport to Madrid at noon. If you’re flexible enough to do this you can expect to save up to 25% on your trip compared to booking a flight in the morning.

Related info for your journey

Find useful and relevant information for your journey from Midway to Madrid. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Madrid from Chicago Midway?

    If you book a flight to Madrid from Chicago Midway, you will be flying to Barajas, which is the city’s only airport. Madrid Barajas (MAD) is located 8.5 mi from the center of Madrid. There are 0 flights from Chicago Midway to Barajas per day from 0 different airlines.

  • How long is the flight from Chicago Midway Airport to Madrid?

    For as low as $463, Delta can have you in Madrid from Chicago Midway Airport in 20h 35m. Chicago Midway Airport and Madrid are separated by a distance of 4187 mi.

  • Can I find deals for flights from Midway to Madrid that include hotel bookings?

    Yes. In addition to deals on Midway to Madrid flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Midway to Madrid?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Midway to Madrid.

  • Can I find deals for business class flights from Midway to Madrid?

    Yes. Cheapflights offers flight deals from Midway to Madrid by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago Midway Airport to Madrid?

    Currently, November is the cheapest month in which you can book a flight from Chicago Midway Airport to Madrid (average of $543). Flying from Chicago Midway Airport to Madrid in June is currently the most expensive (average of $1,054). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Madrid?

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Fuenlabrada
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