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$381+ 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 5/31. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MAD
May 27 — Jun 31
Wed 5/27
Wed 6/3
1 adult, Economy
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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 April 27, 2026.

This Delta deal was found by Cheapflights users on 4/22. 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 10/2810:35 am
MDW
-
MAD
1 stop17h 20m
Delta
Wed 11/1811:55 am
MAD
-
MDW
1 stop16h 50m
Delta
Deal found 4/22$722
This Delta deal was found by Cheapflights users on 4/23. 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 10/121:05 pm
MDW
-
MAD
1 stop16h 10m
Delta
Wed 10/216:00 am
MAD
-
MDW
2 stops17h 50m
Delta
Deal found 4/23$724
This Delta deal was found by Cheapflights users on 4/26. 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.
Tue 11/109:55 am
MDW
-
MAD
2 stops15h 05m
Delta
Tue 11/2410:00 am
MAD
-
MDW
2 stops18h 45m
Delta
Deal found 4/26$726
This Virgin Atlantic deal was found by Cheapflights users on 4/23. 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 10/281:00 pm
MDW
-
MAD
2 stops14h 55m
Virgin Atlantic
Fri 11/610:00 am
MAD
-
MDW
2 stops18h 45m
Virgin Atlantic
Deal found 4/23$727
This Delta deal was found by Cheapflights users on 4/23. 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 10/1410:35 am
MDW
-
MAD
2 stops16h 20m
Delta
Fri 10/236:00 am
MAD
-
MDW
2 stops17h 50m
Delta
Deal found 4/23$729
This Delta deal was found by Cheapflights users on 4/26. 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 11/49:55 am
MDW
-
MAD
2 stops22h 25m
Delta
Wed 11/2510:00 am
MAD
-
MDW
2 stops29h 45m
Delta
Deal found 4/26$731
This Delta deal was found by Cheapflights users on 4/26. 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 11/75:25 pm
MDW
-
MAD
1 stop33h 30m
Delta
Tue 11/2410:00 am
MAD
-
MDW
2 stops30h 52m
Delta
Deal found 4/26$732
This Delta deal was found by Cheapflights users on 4/26. 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 10/121:00 pm
MDW
-
MAD
2 stops16h 15m
Delta
Thu 10/226:00 am
MAD
-
MDW
2 stops17h 50m
Delta
Deal found 4/26$735
This Delta deal was found by Cheapflights users on 4/26. 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 11/86:00 am
MDW
-
MAD
1 stop20h 55m
Delta
Thu 11/266:00 am
MAD
-
MDW
2 stops33h 45m
Delta
Deal found 4/26$736
This Delta deal was found by Cheapflights users on 4/26. 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 11/75:25 pm
MDW
-
MAD
1 stop33h 30m
Delta
Thu 11/2610:00 am
MAD
-
MDW
2 stops42h 45m
Delta
Deal found 4/26$737
This Delta deal was found by Cheapflights users on 4/26. 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 11/45:59 pm
MDW
-
MAD
2 stops14h 21m
Delta
Thu 11/266:00 am
MAD
-
MDW
2 stops33h 45m
Delta
Deal found 4/26$741

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 April 27, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$722
(Virgin Atlantic)

One-way from

$381
(Kiwi.com)

Popular in

December

Cheapest in

October

Average price

$600
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 ($44 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($30 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 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 April 27, 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 9/6

6:00 am-12:15 pm

1 stop23h 15m

Madrid Barajas

Tue 9/15

9:50 am-9:46 pm

1 stop18h 56m

$819

ChicagoMadrid

MDW - MAD

MDWMAD

Chicago Midway

Tue 9/1

1:00 pm-9:30 am

2 stops13h 30m

Madrid Barajas

Tue 9/8

9:50 am-9:46 pm

1 stop18h 56m

$853
Quickest round-trip

ChicagoMadrid

MDW - MAD

MDWMAD

Chicago Midway

Tue 7/28

5:10 pm-12:15 pm

1 stop12h 05m

Madrid Barajas

Tue 8/25

6:00 am-6:05 pm

2 stops19h 05m

$875

ChicagoMadrid

MDW - MAD

MDWMAD

Chicago Midway

Sun 8/9

11:05 am-9:30 am

2 stops15h 25m

Madrid Barajas

Wed 8/26

6:00 am-4:27 pm

2 stops17h 27m

$884

ChicagoMadrid

MDW - MAD

MDWMAD

Chicago Midway

Wed 9/16

1:05 pm-12:15 pm

1 stop16h 10m

Madrid Barajas

Mon 9/28

9:50 am-9:46 pm

1 stop18h 56m

$1,017

ChicagoMadrid

MDW - MAD

MDWMAD

Chicago Midway

Fri 10/2

1:00 pm-12:15 pm

2 stops16h 15m

Madrid Barajas

Sun 10/11

9:50 am-9:45 pm

1 stop18h 55m

$1,026

ChicagoMadrid

MDW - MAD

MDWMAD

Chicago Midway

Sun 7/12

9:20 am-9:55 am

2 stops17h 35m

Madrid Barajas

Tue 7/21

9:50 am-10:15 pm

1 stop19h 25m

$1,067

ChicagoMadrid

MDW - MAD

MDWMAD

Chicago Midway

Wed 9/30

1:05 pm-12:15 pm

1 stop16h 10m

Madrid Barajas

Sat 10/10

6:00 am-4:25 pm

2 stops17h 25m

$1,098

ChicagoMadrid

MDW - MAD

MDWMAD

Chicago Midway

Thu 9/17

1:00 pm-9:55 am

2 stops13h 55m

Madrid Barajas

Sat 10/3

9:50 am-9:46 pm

1 stop18h 56m

$1,151

ChicagoMadrid

MDW - MAD

MDWMAD

Chicago Midway

Thu 9/17

9:30 am-9:55 am

2 stops17h 25m

Madrid Barajas

Sat 10/3

6:00 am-6:31 pm

2 stops19h 31m

$1,152

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/26

Showing 1-10 of 23 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 April.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
OvagoPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
AranGrantPrice Accuracy2 starsTrust Score*2 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 FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago Midway Airport-Madrid flight deals on Cheapflights vs. FlightHub >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 FlightHub the most. FlightHub 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 $855, Virgin Atlantic can have you in Madrid from Chicago Midway Airport in 13h 30m. 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

Traveling to a place near Madrid?

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