HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Madrid

$386+ 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 2/15. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MAD
Nov 26 — Dec 31
Wed 11/26
Wed 12/3
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Midway to Madrid with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 October 27, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$466
(Delta)

One-way from

$386
(Kiwi.com)

Popular in

June

Cheapest in

February

Average price

$557
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. 20% potential increase in price ($177 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($27 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
Search Deals

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 October 27, 2025.

This Delta deal was found by Cheapflights users on 10/25. 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 12/106:00 amMAD - MDW
2 stops19h 00mDelta
Deal found 10/25$466
This KLM deal was found by Cheapflights users on 10/26. 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 KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/2810:35 amMDW - MAD
2 stops14h 25mKLM
Thu 11/271:05 pmMAD - MDW
2 stops17h 35mKLM
Deal found 10/26$468
This Delta deal was found by Cheapflights users on 10/25. 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 12/91:14 pmMDW - MAD
2 stops14h 01mDelta
Tue 12/1611:15 amMAD - MDW
1 stop19h 32mDelta
Deal found 10/25$470
This Delta deal was found by Cheapflights users on 10/26. 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 11/121:15 pmMDW - MAD
2 stops15h 15mDelta
Thu 11/206:00 amMAD - MDW
2 stops19h 08mDelta
Deal found 10/26$481
This Delta deal was found by Cheapflights users on 10/26. 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 11/256:00 amMDW - MAD
2 stops28h 40mDelta
Tue 12/211:00 amMAD - MDW
2 stops38h 00mDelta
Deal found 10/26$482
This Virgin Atlantic deal was found by Cheapflights users on 10/25. 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.
Sun 11/1610:47 amMDW - MAD
1 stop15h 28mVirgin Atlantic
Mon 11/2411:15 amMAD - MDW
1 stop19h 25mVirgin Atlantic
Deal found 10/25$488
This Virgin Atlantic deal was found by Cheapflights users on 10/24. 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.
Mon 11/179:34 amMDW - MAD
2 stops16h 41mVirgin Atlantic
Mon 11/2411:15 amMAD - MDW
1 stop19h 25mVirgin Atlantic
Deal found 10/24$493
This Delta deal was found by Cheapflights users on 10/26. 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 12/36:00 amMDW - MAD
2 stops19h 00mDelta
Sun 12/710:00 amMAD - MDW
2 stops53h 54mDelta
Deal found 10/26$504
This Delta deal was found by Cheapflights users on 10/26. 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 11/1610:47 amMDW - MAD
1 stop15h 28mDelta
Sun 11/236:00 amMAD - MDW
2 stops19h 08mDelta
Deal found 10/26$512
This Delta deal was found by Cheapflights users on 10/26. 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 10/2910:40 amMDW - MAD
2 stops14h 20mDelta
Sat 11/86:00 amMAD - MDW
2 stops19h 25mDelta
Deal found 10/26$518
This Air France deal was found by Cheapflights users on 10/25. 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 Air France is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/91:05 pmMDW - MAD
1 stop13h 10mMultiple Airlines
Tue 12/1611:15 amMAD - MDW
1 stop19h 32mMultiple Airlines
Deal found 10/25$519
This Delta deal was found by Cheapflights users on 10/25. 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 11/306:00 amMDW - MAD
1 stop20h 15mDelta
Tue 12/911:15 amMAD - MDW
1 stop19h 32mDelta
Deal found 10/25$520

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 October 27, 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

Wed 12/3

6:00 am-8:00 am

2 stops19h 00m

Madrid Barajas

Thu 12/11

6:00 am-6:00 pm

2 stops19h 00m

$466

ChicagoMadrid

MDW - MAD

MDWMAD

Chicago Midway

Tue 12/9

1:14 pm-10:15 am

2 stops14h 01m

Madrid Barajas

Tue 12/16

11:15 am-11:47 pm

1 stop19h 32m

$470

ChicagoMadrid

MDW - MAD

MDWMAD

Chicago Midway

Wed 11/26

9:34 am-3:20 pm

2 stops22h 46m

Madrid Barajas

Wed 12/3

6:00 am-11:47 pm

2 stops24h 47m

$481

ChicagoMadrid

MDW - MAD

MDWMAD

Chicago Midway

Wed 11/12

1:15 pm-11:30 am

2 stops15h 15m

Madrid Barajas

Thu 11/20

6:00 am-6:08 pm

2 stops19h 08m

$481

ChicagoMadrid

MDW - MAD

MDWMAD

Chicago Midway

Wed 11/26

1:15 pm-3:20 pm

2 stops19h 05m

Madrid Barajas

Tue 12/2

1:05 pm-6:00 pm

2 stops35h 55m

$482

ChicagoMadrid

MDW - MAD

MDWMAD

Chicago Midway

Tue 11/25

6:00 am-5:40 pm

2 stops28h 40m

Madrid Barajas

Tue 12/2

11:00 am-6:00 pm

2 stops38h 00m

$482

ChicagoMadrid

MDW - MAD

MDWMAD

Chicago Midway

Fri 12/5

12:50 pm-9:15 am

1 stop13h 25m

Madrid Barajas

Fri 12/12

11:15 am-11:47 pm

1 stop19h 32m

$488

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-8:54 am

2 stops53h 54m

$504

ChicagoMadrid

MDW - MAD

MDWMAD

Chicago Midway

Sun 11/30

5:34 pm-9:15 am

1 stop32h 41m

Madrid Barajas

Tue 12/9

11:15 am-11:47 pm

1 stop19h 32m

$520

ChicagoMadrid

MDW - MAD

MDWMAD

Chicago Midway

Sat 11/15

1:26 pm-12:10 pm

2 stops15h 44m

Madrid Barajas

Thu 12/4

11:15 am-11:47 pm

1 stop19h 32m

$520

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/25

Showing 1-10 of 19 results
1
2

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 October.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars
OvagoPrice Accuracy2 starsTrust Score*2 stars
AranGrantPrice Accuracy2 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 eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Chicago Midway Airport-Madrid flight deals on Cheapflights vs. eDreams >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 eDreams the most. eDreams 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

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 October 27, 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 35% on your trip compared to booking a flight in the evening.

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 $466, Delta can have you in Madrid from Chicago Midway Airport in 19h. 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.

See more FAQs

Traveling to a place near Madrid?

Book flights to Madrid if you plan to visit one of these locations
Fuenlabrada
Getafe

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Midway to Madrid

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Madrid flights

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.