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$309+ 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 3/25. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MAD
Apr 11 — Apr 181
Sat 4/11
Sat 4/18
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 March 12, 2026.

This Flighttix deal was found by Cheapflights users on 3/10. 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 Flighttix is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/135:21 pm
MDW
-
MAD
1 stop11h 54m
Virgin Atlantic
Tue 4/2112:45 pm
MAD
-
MDW
1 stop16h 43m
Virgin Atlantic
Deal found 3/10$545
This Delta deal was found by Cheapflights users on 3/9. 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.
Mon 4/135:21 pm
MDW
-
MAD
1 stop11h 54m
Delta
Tue 4/2112:45 pm
MAD
-
MDW
1 stop16h 43m
Delta
Deal found 3/9$552
This Delta deal was found by Cheapflights users on 3/8. 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.
Wed 4/155:21 pm
MDW
-
MAD
1 stop11h 54m
Delta
Wed 4/2212:45 pm
MAD
-
MDW
1 stop16h 43m
Delta
Deal found 3/8$561
This Delta deal was found by Cheapflights users on 3/8. 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.
Wed 11/111:00 pm
MDW
-
MAD
2 stops16h 10m
Delta
Wed 11/1811:15 am
MAD
-
MDW
1 stop17h 30m
Delta
Deal found 3/8$569
This Trip.com deal was found by Cheapflights users on 3/9. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/136:00 am
MDW
-
MAD
1 stop23h 15m
KLM
Tue 4/2112:45 pm
MAD
-
MDW
1 stop16h 43m
KLM
Deal found 3/9$576
This Trip.com deal was found by Cheapflights users on 3/9. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/135:21 pm
MDW
-
MAD
1 stop11h 54m
Multiple Airlines
Tue 4/216:00 am
MAD
-
MDW
2 stops18h 58m
Multiple Airlines
Deal found 3/9$577

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 March 12, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$545
(Flighttix)

One-way from

$309
(Kiwi.com)

Popular in

December

Cheapest in

October

Average price

$673
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. 6% potential increase in price ($44 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 March 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 March 12, 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

Mon 4/27

5:21 pm-12:15 pm

1 stop11h 54m

Madrid Barajas

Mon 5/4

12:45 pm-10:28 pm

1 stop16h 43m

$1,017

ChicagoMadrid

MDW - MAD

MDWMAD

Chicago Midway

Thu 4/2

6:34 pm-3:35 pm

2 stops14h 01m

Madrid Barajas

Fri 4/10

6:00 am-5:54 pm

2 stops18h 54m

$1,021

ChicagoMadrid

MDW - MAD

MDWMAD

Chicago Midway

Wed 3/18

1:10 pm-11:30 am

2 stops16h 20m

Madrid Barajas

Wed 3/25

6:00 am-5:54 pm

2 stops17h 54m

$1,024

ChicagoMadrid

MDW - MAD

MDWMAD

Chicago Midway

Sat 6/6

1:22 pm-11:20 am

2 stops14h 58m

Madrid Barajas

Tue 7/7

9:50 am-6:31 pm

2 stops15h 41m

$1,128

ChicagoMadrid

MDW - MAD

MDWMAD

Chicago Midway

Mon 5/18

9:22 am-9:55 am

2 stops17h 33m

Madrid Barajas

Mon 6/8

9:50 am-6:31 pm

2 stops15h 41m

$1,152

ChicagoMadrid

MDW - MAD

MDWMAD

Chicago Midway

Thu 6/4

7:40 am-1:40 pm

2 stops23h 00m

Madrid Barajas

Tue 6/16

7:05 am-7:20 pm

2 stops19h 15m

$1,157

ChicagoMadrid

MDW - MAD

MDWMAD

Chicago Midway

Tue 3/24

9:35 am-7:00 am

2 stops15h 25m

Madrid Barajas

Mon 3/30

12:45 pm-12:02 pm

1 stop30h 17m

$1,160

ChicagoMadrid

MDW - MAD

MDWMAD

Chicago Midway

Wed 4/1

6:34 pm-4:45 pm

2 stops15h 11m

Madrid Barajas

Sun 4/5

6:00 am-5:54 pm

2 stops18h 54m

$1,170

ChicagoMadrid

MDW - MAD

MDWMAD

Chicago Midway

Wed 5/20

6:23 am-12:15 pm

1 stop22h 52m

Madrid Barajas

Sat 6/6

9:50 am-9:09 pm

1 stop18h 19m

$1,205

ChicagoMadrid

MDW - MAD

MDWMAD

Chicago Midway

Wed 5/27

10:55 am-12:15 pm

1 stop18h 20m

Madrid Barajas

Wed 6/3

9:50 am-9:09 pm

1 stop18h 19m

$1,250

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/7

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 March.
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 $1,017, Virgin Atlantic can have you in Madrid from Chicago Midway Airport in 11h 54m. 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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