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$334+ 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 8/17. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MAD
Jul 6 — Jul 131
Mon 7/6
Mon 7/13
1 adult, Economy
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Find cheap flights from Midway to Madrid with Cheapflights

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Cheap 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 June 6, 2026.

This Delta deal was found by Cheapflights users on 6/5. 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 8/51:27 pm
MDW
-
MAD
2 stops15h 43m
Delta
Thu 8/209:50 am
MAD
-
MDW
2 stops15h 43m
Delta
Deal found 6/5$827
This Delta deal was found by Cheapflights users on 6/6. 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.
Fri 10/166:45 pm
MDW
-
MAD
2 stops14h 40m
Delta
Sat 10/3111:55 am
MAD
-
MDW
1 stop15h 50m
Delta
Deal found 6/6$831
This Delta deal was found by Cheapflights users on 6/6. 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.
Fri 10/26:51 pm
MDW
-
MAD
2 stops14h 34m
Delta
Sun 10/116:00 am
MAD
-
MDW
2 stops17h 50m
Delta
Deal found 6/6$833
This Virgin Atlantic deal was found by Cheapflights users on 6/4. 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 Virgin Atlantic is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/149:30 am
MDW
-
MAD
2 stops19h 45m
Virgin Atlantic
Wed 10/219:50 am
MAD
-
MDW
2 stops15h 47m
Virgin Atlantic
Deal found 6/4$847
This KLM deal was found by Cheapflights users on 6/4. 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 KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/1412:46 pm
MDW
-
MAD
1 stop16h 29m
KLM
Fri 8/219:50 am
MAD
-
MDW
1 stop13h 25m
KLM
Deal found 6/4$864
This Delta deal was found by Cheapflights users on 6/5. 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 8/245:10 pm
MDW
-
MAD
1 stop12h 05m
Delta
Sat 9/56:00 am
MAD
-
MDW
2 stops16h 57m
Delta
Deal found 6/5$865
This Delta deal was found by Cheapflights users on 6/3. 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 9/95:59 pm
MDW
-
MAD
2 stops14h 36m
Delta
Mon 9/149:50 am
MAD
-
MDW
1 stop13h 21m
Delta
Deal found 6/3$868
This Delta deal was found by Cheapflights users on 6/3. 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 9/65:45 pm
MDW
-
MAD
2 stops14h 50m
Delta
Sat 9/196:00 am
MAD
-
MDW
2 stops19h 33m
Delta
Deal found 6/3$870
This Delta deal was found by Cheapflights users on 6/4. 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.
Sat 8/16:55 pm
MDW
-
MAD
2 stops14h 30m
Delta
Tue 8/259:50 am
MAD
-
MDW
1 stop13h 25m
Delta
Deal found 6/4$873
This Delta deal was found by Cheapflights users on 6/2. 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.
Thu 9/1010:35 am
MDW
-
MAD
1 stop18h 40m
Delta
Wed 9/169:50 am
MAD
-
MDW
1 stop19h 35m
Delta
Deal found 6/2$874

Find 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 June 6, 2026.

Most accurate provider

Ovago
3 stars

Most trusted provider

Ovago
3 stars

Round-trip from

$827
(Delta)

One-way from

$334
(Virgin Atlantic)

Popular in

December

Cheapest in

October

Average price

$936
Provider with most accurate pricing for Chicago Midway-Madrid Barajas flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago Midway-Madrid Barajas flights.
Search Deals
From Chicago Midway to Madrid Barajas
Search Deals
One-way flight from Chicago Midway to Madrid Barajas
Search Deals
Highest demand for flights based on searches. 5% potential increase in price ($40 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($28 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in June 2026
Search Deals

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 June 6, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Madrid that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoMadrid

MDW - MAD

MDWMAD

Chicago Midway

Sun 8/23

5:10 pm-12:15 pm

1 stop12h 05m

Madrid Barajas

Fri 8/28

9:50 am-10:36 pm

1 stop19h 46m

$906

ChicagoMadrid

MDW - MAD

MDWMAD

Chicago Midway

Mon 7/27

11:05 am-9:30 am

2 stops15h 25m

Madrid Barajas

Wed 8/5

12:20 pm-10:36 pm

2 stops17h 16m

$1,004

ChicagoMadrid

MDW - MAD

MDWMAD

Chicago Midway

Sat 8/8

1:27 pm-9:30 am

2 stops13h 03m

Madrid Barajas

Tue 8/18

6:00 am-6:33 pm

2 stops19h 33m

$1,046

ChicagoMadrid

MDW - MAD

MDWMAD

Chicago Midway

Wed 8/12

10:54 am-12:15 pm

1 stop18h 21m

Madrid Barajas

Thu 8/20

9:50 am-10:36 pm

1 stop19h 46m

$1,100

ChicagoMadrid

MDW - MAD

MDWMAD

Chicago Midway

Sat 8/29

6:42 pm-4:25 pm

2 stops14h 43m

Madrid Barajas

Mon 9/7

6:00 am-6:01 pm

2 stops19h 01m

$1,116

ChicagoMadrid

MDW - MAD

MDWMAD

Chicago Midway

Mon 7/6

1:26 pm-11:20 am

2 stops14h 54m

Madrid Barajas

Fri 7/17

6:00 am-6:25 pm

2 stops19h 25m

$1,186

ChicagoMadrid

MDW - MAD

MDWMAD

Chicago Midway

Tue 7/21

1:49 pm-11:20 am

2 stops14h 31m

Madrid Barajas

Fri 7/31

6:00 am-6:25 pm

2 stops19h 25m

$1,243

ChicagoMadrid

MDW - MAD

MDWMAD

Chicago Midway

Sat 8/15

9:24 am-9:55 am

2 stops17h 31m

Madrid Barajas

Sat 8/22

9:50 am-6:33 pm

2 stops15h 43m

$1,418

ChicagoMadrid

MDW - MAD

MDWMAD

Chicago Midway

Wed 8/5

10:54 am-12:15 pm

1 stop18h 21m

Madrid Barajas

Sat 8/8

9:50 am-10:36 pm

1 stop19h 46m

$1,471
Quickest round-trip

ChicagoMadrid

MDW - MAD

MDWMAD

Chicago Midway

Sat 8/8

10:56 am-12:15 pm

1 stop18h 19m

Madrid Barajas

Tue 8/18

9:50 am-4:15 pm

1 stop13h 25m

$1,570

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/3

Showing 1-10 of 22 resultsSorted by cheapest first
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Compare providers for flights from Midway to Madrid

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Midway to Madrid in June.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
OvagoPrice Accuracy3 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
AranGrantPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago Midway Airport-Madrid flights, users find the pricing of Ovago to be most consistent on Cheapflights vs. Ovago Users can find the same prices on Chicago Midway Airport-Madrid flight deals on Cheapflights vs. Ovago >95% of the time. Price accuracy is based on data collected from Chicago Midway Airport-Madrid flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago Midway Airport-Madrid flights, Cheapflights users trust Ovago the most. Ovago has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago Midway Airport-Madrid flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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

How often are flights from Chicago to Madrid delayed?

About 0% of weekly flights between Chicago and Madrid have experienced delays in the past year, with the average delay time being 0 minutes.

What is the most punctual flight time for Chicago to Madrid flights?

Historically, flights departing in the early afternoon are less likely to be delayed, whereas flights leaving in the early afternoon tend to experience delays more often.

What day of the week experiences the fewest flight delays on this route?

Friday tends to have the lowest number of delays on this route, whereas Friday has historically faced a higher average of delays compared to other days of the week.

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 $906, Delta can have you in Madrid from Chicago Midway Airport in 12h 05m. Chicago Midway Airport and Madrid are separated by a distance of 4187 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • 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.

See more FAQs

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