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Cheap flights from Chicago Midway Airport to Madrid from $318

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago Midway Airport to Madrid departing on 5/2. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

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Find the cheapest flights from Chicago Midway Airport to Madrid

Cheap round-trip flights

Enter your travel dates to find the best prices.
Virgin Atlantic Logo
5:21 pm - 12:15 pm
MDW
-
MAD
11h 54m
1 stop
Virgin Atlantic Logo
12:45 pm - 10:28 pm
MAD
-
MDW
16h 43m
1 stop
$600Virgin Atlantic
Mon, Apr 20 - Tue, Apr 28
Virgin Atlantic Logo
5:21 pm - 12:15 pm
MDW
-
MAD
11h 54m
1 stop
Virgin Atlantic Logo
12:45 pm - 10:28 pm
MAD
-
MDW
16h 43m
1 stop
$611Virgin Atlantic
Mon, Apr 13 - Tue, Apr 21
Delta Logo
12:52 pm - 12:15 pm
MDW
-
MAD
16h 23m
1 stop
Delta Logo
6:00 am - 4:26 pm
MAD
-
MDW
17h 26m
2 stops
$612Delta
Mon, Apr 13 - Tue, Apr 21
Virgin Atlantic Logo
10:41 am - 9:55 am
MDW
-
MAD
16h 14m
2 stops
Virgin Atlantic Logo
12:45 pm - 10:28 pm
MAD
-
MDW
16h 43m
1 stop
$615Virgin Atlantic
Wed, Apr 15 - Thu, Apr 23
Delta Logo
1:24 pm - 9:55 am
MDW
-
MAD
13h 31m
2 stops
Delta Logo
6:00 am - 5:58 pm
MAD
-
MDW
18h 58m
2 stops
$616Delta
Mon, Apr 13 - Tue, Apr 21
Delta Logo
10:41 am - 9:55 am
MDW
-
MAD
16h 14m
2 stops
Delta Logo
6:00 am - 5:58 pm
MAD
-
MDW
18h 58m
2 stops
$617Delta
Wed, Apr 15 - Thu, Apr 23
Delta Logo
1:10 pm - 9:30 am
MDW
-
MAD
13h 20m
2 stops
Delta Logo
12:45 pm - 10:28 pm
MAD
-
MDW
16h 43m
1 stop
$619Delta
Wed, Apr 8 - Wed, Apr 15
Delta Logo
1:10 pm - 9:30 am
MDW
-
MAD
13h 20m
2 stops
Delta Logo
6:00 am - 4:29 pm
MAD
-
MDW
17h 29m
2 stops
$621Delta
Wed, Apr 8 - Wed, Apr 15
Delta Logo
1:24 pm - 9:55 am
MDW
-
MAD
13h 31m
2 stops
Delta Logo
6:00 am - 4:26 pm
MAD
-
MDW
17h 26m
2 stops
$624Delta
Mon, Apr 20 - Wed, Apr 29
Delta Logo
6:07 pm - 12:15 pm
MDW
-
MAD
11h 08m
1 stop
Delta Logo
12:45 pm - 10:28 pm
MAD
-
MDW
16h 43m
1 stop
$661Delta
Fri, Apr 10 - Fri, Apr 17

Air France flights from Chicago Midway Airport to Madrid

Our best Air France deals on Chicago Midway Airport to Madrid flight tickets
Air France
Apr 13
MDW5:21 pmChicago Midway
11h 54m
1 stop
MAD12:15 pmMadrid Barajas
Apr 20
MAD12:45 pmMadrid Barajas
16h 43m
1 stop
MDW10:28 pmChicago Midway
$711
Air France
Apr 28
MDW5:21 pmChicago Midway
11h 54m
1 stop
MAD12:15 pmMadrid Barajas
May 12
MAD9:50 amMadrid Barajas
13h 22m
1 stop
MDW4:12 pmChicago Midway
$747
Air France
Apr 21
MDW5:21 pmChicago Midway
11h 54m
1 stop
MAD12:15 pmMadrid Barajas
May 21
MAD9:50 amMadrid Barajas
18h 19m
1 stop
MDW9:09 pmChicago Midway
$748

Virgin Atlantic flights from Chicago Midway Airport to Madrid

Our best Virgin Atlantic deals on Chicago Midway Airport to Madrid flight tickets
Virgin Atlantic
Apr 15
MDW10:41 amChicago Midway
16h 14m
2 stops
MAD9:55 amMadrid Barajas
Apr 23
MAD12:45 pmMadrid Barajas
16h 43m
1 stop
MDW10:28 pmChicago Midway
$615
Virgin Atlantic
Apr 10
MDW1:10 pmChicago Midway
16h 05m
2 stops
MAD12:15 pmMadrid Barajas
Apr 17
MAD12:45 pmMadrid Barajas
16h 43m
1 stop
MDW10:28 pmChicago Midway
$665
Virgin Atlantic
Apr 22
MDW1:24 pmChicago Midway
15h 51m
2 stops
MAD12:15 pmMadrid Barajas
Apr 29
MAD12:45 pmMadrid Barajas
16h 43m
1 stop
MDW10:28 pmChicago Midway
$680

momondo Fare Finder

 
Customize your flight search to find flights from Chicago Midway Airport 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, momondo users made 832,500 searches. Data last updated March 17, 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 4/20

5:21 pm-12:15 pm

1 stop11h 54m

Madrid Barajas

Tue 4/28

12:45 pm-10:28 pm

1 stop16h 43m

$600

ChicagoMadrid

MDW - MAD

MDWMAD

Chicago Midway

Mon 4/13

5:21 pm-12:15 pm

1 stop11h 54m

Madrid Barajas

Tue 4/21

12:45 pm-10:28 pm

1 stop16h 43m

$611

ChicagoMadrid

MDW - MAD

MDWMAD

Chicago Midway

Mon 4/13

12:52 pm-12:15 pm

1 stop16h 23m

Madrid Barajas

Tue 4/21

6:00 am-4:26 pm

2 stops17h 26m

$612

ChicagoMadrid

MDW - MAD

MDWMAD

Chicago Midway

Wed 4/15

10:41 am-9:55 am

2 stops16h 14m

Madrid Barajas

Thu 4/23

12:45 pm-10:28 pm

1 stop16h 43m

$615

ChicagoMadrid

MDW - MAD

MDWMAD

Chicago Midway

Mon 4/13

1:24 pm-9:55 am

2 stops13h 31m

Madrid Barajas

Tue 4/21

6:00 am-5:58 pm

2 stops18h 58m

$616

ChicagoMadrid

MDW - MAD

MDWMAD

Chicago Midway

Wed 4/15

10:41 am-9:55 am

2 stops16h 14m

Madrid Barajas

Thu 4/23

6:00 am-5:58 pm

2 stops18h 58m

$617

ChicagoMadrid

MDW - MAD

MDWMAD

Chicago Midway

Wed 4/8

1:10 pm-9:30 am

2 stops13h 20m

Madrid Barajas

Wed 4/15

12:45 pm-10:28 pm

1 stop16h 43m

$619

ChicagoMadrid

MDW - MAD

MDWMAD

Chicago Midway

Wed 4/8

1:10 pm-9:30 am

2 stops13h 20m

Madrid Barajas

Wed 4/15

6:00 am-4:29 pm

2 stops17h 29m

$621

ChicagoMadrid

MDW - MAD

MDWMAD

Chicago Midway

Mon 4/20

1:24 pm-9:55 am

2 stops13h 31m

Madrid Barajas

Wed 4/29

6:00 am-4:26 pm

2 stops17h 26m

$624
Quickest round-trip

ChicagoMadrid

MDW - MAD

MDWMAD

Chicago Midway

Fri 4/10

6:07 pm-12:15 pm

1 stop11h 08m

Madrid Barajas

Fri 4/17

12:45 pm-10:28 pm

1 stop16h 43m

$661

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Madrid from

How to get the cheapest flight ticket from Chicago Midway Airport to Madrid

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest day to depart on your flight to Madrid?

The cheapest day to depart on your flight to Madrid is on a Wednesday when prices can be found for as low as $747. This is often the case because there is less demand to fly during this day of the week. Be sure to avoid booking your departure on a Saturday as prices are generally higher than usual. According to our data, the average ticket price to Madrid on Saturday is $899.

What is the cheapest time of day to depart on your flight to Madrid?

Flying to Madrid from Chicago Midway Airport in the evening is the least expensive time of day to depart. momondo users have found prices as low as $794 when looking at flights departing in the evening. Flights to Madrid are more costly in the afternoon, with an average ticket price of $805. Departure times in the afternoon fall within the peak daily travel times, which is why tickets can be more expensive.

Can stopping save me money on Chicago Midway Airport to Madrid flights?

You could potentially save up to 65% on your flight if you consider stops on a Chicago Midway Airport to Madrid flight.

When to book flights from Chicago Midway Airport to Madrid

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago Midway Airport to Madrid according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Chicago Midway Airport to Madrid (MDW to MAD) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to Madrid

Fastest flight time

11h 50m

Direct flights

None
The fastest flight from Chicago Midway Airport to Madrid takes 11h 50m
There are no direct flights from Chicago Midway Airport to Madrid. There are no popular flight routes from Chicago Midway Airport to Madrid.
Search flight deals

  • How far is Chicago Midway to Madrid Barajas by plane?

    The distance between Chicago Midway and Madrid Barajas is about 4184.0 mi. By plane, this route typically takes 11h 50m.

  • When did momondo last update prices for flights from Chicago Midway Airport to Madrid Barajas Airport?

    Prices for flights from Chicago Midway Airport to Madrid Barajas Airport are updated daily.

  • How old do you have to be to fly from Chicago Midway Airport to Madrid Barajas Airport?

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago Midway Airport to Madrid Barajas Airport.

  • What documentation or ID do you need to fly to Madrid Barajas Airport?

    The required travel and health documents for your Madrid Barajas Airport trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Madrid Barajas Airport. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

Traveling to a place near Madrid?

Book flights to Madrid if you plan to visit one of these locations
Toledo
Segovia
Fuenlabrada
Getafe
Cuenca
San Lorenzo de El Escorial
Guadalajara

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Madrid?

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Chicago to Madrid. Millions of users trust and use momondo every year so you are in good hands.

Can I find flights from Chicago to Madrid with flexible booking policies on momondo?

Yes. momondo allows you to filter the results for Chicago to Madrid flights to just show those with flexible booking policies.

How can momondo help me find flights from Chicago to Madrid?

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Madrid from Chicago.

I’m not ready to book a flight from Chicago to Madrid right now. Can momondo alert me if prices change?

Yes momondo offers price alerts on flights to Madrid from Chicago. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.

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Cabin classes currently available on flights to Madrid

List of cabin classes available on flights landing in Madrid. Availability may vary depending on flight origin and airline.
First Class to Madrid
Business Class to Madridfrom $1,595