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Cheap flights from Chicago Midway Airport to Madrid from $392

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 5/29. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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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.
Delta Logo
5:25 pm - 12:15 pm
MDW
-
MAD
11h 50m
1 stop
Delta Logo
11:55 am - 9:45 pm
MAD
-
MDW
15h 50m
1 stop
$722Delta
Mon, Oct 12 - Fri, Oct 30
Delta Logo
5:25 pm - 12:15 pm
MDW
-
MAD
11h 50m
1 stop
Delta Logo
6:00 am - 4:25 pm
MAD
-
MDW
17h 25m
2 stops
$724Delta
Mon, Oct 12 - Wed, Oct 21
Virgin Atlantic Logo
9:30 am - 12:15 pm
MDW
-
MAD
19h 45m
2 stops
Virgin Atlantic Logo
9:50 am - 4:25 pm
MAD
-
MDW
13h 35m
1 stop
$726Virgin Atlantic
Sun, Oct 4 - Thu, Oct 8
Virgin Atlantic Logo
1:27 pm - 12:15 pm
MDW
-
MAD
15h 48m
2 stops
Virgin Atlantic Logo
10:00 am - 9:45 pm
MAD
-
MDW
18h 45m
2 stops
$727Virgin Atlantic
Tue, Aug 11 - Fri, Dec 11
Delta Logo
1:00 pm - 12:15 pm
MDW
-
MAD
16h 15m
2 stops
Delta Logo
6:00 am - 4:25 pm
MAD
-
MDW
17h 25m
2 stops
$728Delta
Mon, Oct 12 - Wed, Oct 21
KLM Logo
1:05 pm - 12:15 pm
MDW
-
MAD
16h 10m
1 stop
KLM Logo
9:50 am - 9:45 pm
MAD
-
MDW
18h 55m
1 stop
$764KLM
Sun, Sep 27 - Sun, Oct 11
Delta Logo
1:05 pm - 12:15 pm
MDW
-
MAD
16h 10m
1 stop
Delta Logo
6:00 am - 6:37 pm
MAD
-
MDW
18h 37m
2 stops
$774Delta
Thu, Oct 15 - Thu, Oct 29
Delta Logo
1:00 pm - 12:15 pm
MDW
-
MAD
16h 15m
2 stops
Delta Logo
6:00 am - 6:31 pm
MAD
-
MDW
19h 31m
2 stops
$778Delta
Sun, Sep 20 - Sat, Oct 3
Delta Logo
1:16 pm - 12:10 pm
MDW
-
MAD
15h 54m
2 stops
Delta Logo
11:55 am - 9:45 pm
MAD
-
MDW
16h 50m
1 stop
$781Delta
Sat, Aug 8 - Wed, Dec 16
Delta Logo
1:16 pm - 12:10 pm
MDW
-
MAD
15h 54m
2 stops
Delta Logo
10:00 am - 9:45 pm
MAD
-
MDW
18h 45m
2 stops
$786Delta
Sat, Aug 8 - Wed, Dec 16

Virgin Atlantic flights from Chicago Midway Airport to Madrid

Our best Virgin Atlantic deals on Chicago Midway Airport to Madrid flight tickets
Virgin Atlantic
Oct 4
MDW9:30 amChicago Midway
19h 45m
2 stops
MAD12:15 pmMadrid Barajas
Oct 8
MAD9:50 amMadrid Barajas
13h 35m
1 stop
MDW4:25 pmChicago Midway
$726
Virgin Atlantic
Aug 11
MDW1:27 pmChicago Midway
15h 48m
2 stops
MAD12:15 pmMadrid Barajas
Dec 11
MAD10:00 amMadrid Barajas
18h 45m
2 stops
MDW9:45 pmChicago Midway
$727
Virgin Atlantic
Sep 28
MDW1:05 pmChicago Midway
16h 10m
1 stop
MAD12:15 pmMadrid Barajas
Oct 13
MAD9:50 amMadrid Barajas
18h 55m
1 stop
MDW9:45 pmChicago Midway
$795

Delta flights from Chicago Midway Airport to Madrid

Our best Delta deals on Chicago Midway Airport to Madrid flight tickets
Delta
Oct 12
MDW5:25 pmChicago Midway
11h 50m
1 stop
MAD12:15 pmMadrid Barajas
Oct 30
MAD11:55 amMadrid Barajas
15h 50m
1 stop
MDW9:45 pmChicago Midway
$722
Delta
Oct 12
MDW5:25 pmChicago Midway
11h 50m
1 stop
MAD12:15 pmMadrid Barajas
Oct 21
MAD6:00 amMadrid Barajas
17h 25m
2 stops
MDW4:25 pmChicago Midway
$724
Delta
Oct 12
MDW1:00 pmChicago Midway
16h 15m
2 stops
MAD12:15 pmMadrid Barajas
Oct 21
MAD6:00 amMadrid Barajas
17h 25m
2 stops
MDW4:25 pmChicago Midway
$728

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 May 3, 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
Quickest round-trip

ChicagoMadrid

MDW - MAD

MDWMAD

Chicago Midway

Mon 10/12

5:25 pm-12:15 pm

1 stop11h 50m

Madrid Barajas

Fri 10/30

11:55 am-9:45 pm

1 stop15h 50m

$722

ChicagoMadrid

MDW - MAD

MDWMAD

Chicago Midway

Mon 10/12

5:25 pm-12:15 pm

1 stop11h 50m

Madrid Barajas

Wed 10/21

6:00 am-4:25 pm

2 stops17h 25m

$724

ChicagoMadrid

MDW - MAD

MDWMAD

Chicago Midway

Sun 10/4

9:30 am-12:15 pm

2 stops19h 45m

Madrid Barajas

Thu 10/8

9:50 am-4:25 pm

1 stop13h 35m

$726

ChicagoMadrid

MDW - MAD

MDWMAD

Chicago Midway

Tue 8/11

1:27 pm-12:15 pm

2 stops15h 48m

Madrid Barajas

Fri 12/11

10:00 am-9:45 pm

2 stops18h 45m

$727

ChicagoMadrid

MDW - MAD

MDWMAD

Chicago Midway

Mon 10/12

1:00 pm-12:15 pm

2 stops16h 15m

Madrid Barajas

Wed 10/21

6:00 am-4:25 pm

2 stops17h 25m

$728

ChicagoMadrid

MDW - MAD

MDWMAD

Chicago Midway

Sun 9/27

1:05 pm-12:15 pm

1 stop16h 10m

Madrid Barajas

Sun 10/11

9:50 am-9:45 pm

1 stop18h 55m

$764

ChicagoMadrid

MDW - MAD

MDWMAD

Chicago Midway

Thu 10/15

1:05 pm-12:15 pm

1 stop16h 10m

Madrid Barajas

Thu 10/29

6:00 am-6:37 pm

2 stops18h 37m

$774

ChicagoMadrid

MDW - MAD

MDWMAD

Chicago Midway

Sun 9/20

1:00 pm-12:15 pm

2 stops16h 15m

Madrid Barajas

Sat 10/3

6:00 am-6:31 pm

2 stops19h 31m

$778

ChicagoMadrid

MDW - MAD

MDWMAD

Chicago Midway

Sat 8/8

1:16 pm-12:10 pm

2 stops15h 54m

Madrid Barajas

Wed 12/16

11:55 am-9:45 pm

1 stop16h 50m

$781

ChicagoMadrid

MDW - MAD

MDWMAD

Chicago Midway

Sat 8/8

1:16 pm-12:10 pm

2 stops15h 54m

Madrid Barajas

Wed 12/16

10:00 am-9:45 pm

2 stops18h 45m

$786

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 $729. 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 $861.

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

Flying to Madrid from Chicago Midway Airport in the afternoon is the least expensive time of day to depart. momondo users have found prices as low as $792 when looking at flights departing in the afternoon. Flights to Madrid are more costly in the evening, with an average ticket price of $799. Departure times in the evening 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

12h 05m

Direct flights

None
The fastest flight from Chicago Midway Airport to Madrid takes 12h 05m
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

Frequently asked questions about flying from Chicago Midway Airport to Madrid

  • 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 12h 05m.

  • 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 $1,598