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Cheap flights from Chicago Midway Airport to Madrid from $354

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 1/18. 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
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.
KLM Logo
10:46 am - 9:15 am
MDW
-
MAD
15h 29m1 stop
KLM Logo
11:15 am - 10:22 pm
MAD
-
MDW
18h 07m1 stop
$489KLM
Mon, Jan 26 - Tue, Feb 3
Delta Logo
5:31 pm - 12:15 pm
MDW
-
MAD
11h 44m1 stop
Delta Logo
6:00 am - 5:54 pm
MAD
-
MDW
18h 54m2 stops
$491Delta
Mon, Apr 20 - Wed, Apr 29
Delta Logo
12:48 pm - 9:15 am
MDW
-
MAD
13h 27m1 stop
Delta Logo
6:00 am - 5:29 pm
MAD
-
MDW
18h 29m2 stops
$492Delta
Mon, Jan 26 - Tue, Feb 3
Delta Logo
6:00 am - 8:00 am
MDW
-
MAD
19h 00m2 stops
Delta Logo
10:00 am - 10:31 pm
MAD
-
MDW
19h 31m2 stops
$493Delta
Wed, Feb 11 - Wed, Feb 18
KLM Logo
6:14 pm - 9:15 am
MDW
-
MAD
32h 01m1 stop
KLM Logo
11:15 am - 10:22 pm
MAD
-
MDW
18h 07m1 stop
$494KLM
Sun, Jan 25 - Tue, Feb 3
Delta Logo
6:30 pm - 3:20 pm
MDW
-
MAD
13h 50m2 stops
Delta Logo
6:00 am - 6:36 pm
MAD
-
MDW
19h 36m2 stops
$496Delta
Sun, Jan 11 - Tue, Jan 20
Delta Logo
6:34 pm - 3:35 pm
MDW
-
MAD
14h 01m2 stops
Delta Logo
12:40 pm - 10:29 pm
MAD
-
MDW
16h 49m2 stops
$497Delta
Tue, Apr 21 - Tue, Apr 28
Delta Logo
10:49 am - 10:15 am
MDW
-
MAD
16h 26m2 stops
Delta Logo
10:05 am - 10:31 pm
MAD
-
MDW
18h 26m1 stop
$499Delta
Wed, Mar 4 - Tue, Mar 10
Delta Logo
10:49 am - 10:15 am
MDW
-
MAD
16h 26m2 stops
Delta Logo
6:00 am - 6:40 pm
MAD
-
MDW
18h 40m2 stops
$502Delta
Wed, Mar 4 - Tue, Mar 10
Delta Logo
6:25 am - 7:00 am
MDW
-
MAD
18h 35m2 stops
Delta Logo
12:35 pm - 8:53 am
MAD
-
MDW
26h 18m2 stops
$503Delta
Tue, Mar 17 - Tue, Mar 24

Virgin Atlantic flights from Chicago Midway Airport to Madrid

Our best Virgin Atlantic deals on Chicago Midway Airport to Madrid flight tickets
Virgin Atlantic
Jan 23
MDW12:48 pmChicago Midway
13h 27m
1 stop
MAD9:15 amMadrid Barajas
Jan 27
MAD11:15 amMadrid Barajas
18h 07m
1 stop
MDW10:22 pmChicago Midway
$539
Find similar
Virgin Atlantic
Mar 4
MDW10:49 amChicago Midway
15h 26m
1 stop
MAD9:15 amMadrid Barajas
Mar 10
MAD10:05 amMadrid Barajas
18h 26m
1 stop
MDW10:31 pmChicago Midway
$554
Find similar
Virgin Atlantic
Jan 14
MDW9:32 amChicago Midway
16h 43m
2 stops
MAD9:15 amMadrid Barajas
Jan 28
MAD10:00 amMadrid Barajas
19h 22m
2 stops
MDW10:22 pmChicago Midway
$558
Find similar

Delta flights from Chicago Midway Airport to Madrid

Our best Delta deals on Chicago Midway Airport to Madrid flight tickets
Delta
Apr 20
MDW5:31 pmChicago Midway
11h 44m
1 stop
MAD12:15 pmMadrid Barajas
Apr 29
MAD6:00 amMadrid Barajas
18h 54m
2 stops
MDW5:54 pmChicago Midway
$491
Find similar
Delta
Jan 26
MDW12:48 pmChicago Midway
13h 27m
1 stop
MAD9:15 amMadrid Barajas
Feb 3
MAD6:00 amMadrid Barajas
18h 29m
2 stops
MDW5:29 pmChicago Midway
$492
Find similar
Delta
Feb 11
MDW6:00 amChicago Midway
19h 00m
2 stops
MAD8:00 amMadrid Barajas
Feb 18
MAD10:00 amMadrid Barajas
19h 31m
2 stops
MDW10:31 pmChicago Midway
$493
Find similar

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 December 28, 2025.
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

ChicagoMadrid

MDW - MAD

MDWMAD

Chicago Midway

Mon 1/26

10:46 am-9:15 am

1 stop15h 29m

Madrid Barajas

Tue 2/3

11:15 am-10:22 pm

1 stop18h 07m

$489

ChicagoMadrid

MDW - MAD

MDWMAD

Chicago Midway

Mon 4/20

5:31 pm-12:15 pm

1 stop11h 44m

Madrid Barajas

Wed 4/29

6:00 am-5:54 pm

2 stops18h 54m

$491

ChicagoMadrid

MDW - MAD

MDWMAD

Chicago Midway

Mon 1/26

12:48 pm-9:15 am

1 stop13h 27m

Madrid Barajas

Tue 2/3

6:00 am-5:29 pm

2 stops18h 29m

$492

ChicagoMadrid

MDW - MAD

MDWMAD

Chicago Midway

Wed 2/11

6:00 am-8:00 am

2 stops19h 00m

Madrid Barajas

Wed 2/18

10:00 am-10:31 pm

2 stops19h 31m

$493

ChicagoMadrid

MDW - MAD

MDWMAD

Chicago Midway

Sun 1/25

6:14 pm-9:15 am

1 stop32h 01m

Madrid Barajas

Tue 2/3

11:15 am-10:22 pm

1 stop18h 07m

$494

ChicagoMadrid

MDW - MAD

MDWMAD

Chicago Midway

Sun 1/11

6:30 pm-3:20 pm

2 stops13h 50m

Madrid Barajas

Tue 1/20

6:00 am-6:36 pm

2 stops19h 36m

$496

ChicagoMadrid

MDW - MAD

MDWMAD

Chicago Midway

Tue 4/21

6:34 pm-3:35 pm

2 stops14h 01m

Madrid Barajas

Tue 4/28

12:40 pm-10:29 pm

2 stops16h 49m

$497

ChicagoMadrid

MDW - MAD

MDWMAD

Chicago Midway

Wed 3/4

10:49 am-10:15 am

2 stops16h 26m

Madrid Barajas

Tue 3/10

10:05 am-10:31 pm

1 stop18h 26m

$499

ChicagoMadrid

MDW - MAD

MDWMAD

Chicago Midway

Wed 3/4

10:49 am-10:15 am

2 stops16h 26m

Madrid Barajas

Tue 3/10

6:00 am-6:40 pm

2 stops18h 40m

$502

ChicagoMadrid

MDW - MAD

MDWMAD

Chicago Midway

Tue 3/17

6:25 am-7:00 am

2 stops18h 35m

Madrid Barajas

Tue 3/24

12:35 pm-8:53 am

2 stops26h 18m

$503

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 $766. 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 $944.

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

Flying to Madrid from Chicago Midway Airport in the morning is the least expensive time of day to depart. momondo users have found prices as low as $812 when looking at flights departing in the morning. Flights to Madrid are more costly at noon, with an average ticket price of $897. Departure times at noon 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 45m

Direct flights

None
The fastest flight from Chicago Midway Airport to Madrid takes 12h 45m
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 12h 45m.

  • 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
Getafe
Fuenlabrada
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 $1,762