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Cheap flights from Chicago Midway Airport to Madrid from $329

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 11/11. 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

Find the cheapest flights from Chicago Midway Airport to Madrid

Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
11:45 am - 12:40 pmMDW  Chicago Midway-MAD Madrid Barajas
17h 55m2 stops Toronto Island Montreal Pierre Elliott Trudeau Intl
Multiple Airlines Logo
2:10 pm - 11:00 amMAD  Madrid Barajas-MDW Chicago Midway
27h 50m2 stops Montreal Pierre Elliott Trudeau Intl Toronto Island
$707Multiple Airlines
Mon, Sep 14 - Mon, Sep 21
KLM Logo
10:35 am - 11:45 amMDW  Chicago Midway-MAD Madrid Barajas
18h 10m1 stop Atlanta Hartsfield-Jackson
KLM Logo
6:05 am - 4:25 pmMAD  Madrid Barajas-MDW Chicago Midway
17h 20m2 stops Amsterdam Schiphol Atlanta Hartsfield-Jackson
$717KLM
Wed, Jan 20 - Wed, Jan 27
Air France Logo
12:45 pm - 9:45 amMDW  Chicago Midway-MAD Madrid Barajas
15h 00m1 stop Atlanta Hartsfield-Jackson
Air France Logo
12:20 pm - 10:56 pmMAD  Madrid Barajas-MDW Chicago Midway
17h 36m1 stop Atlanta Hartsfield-Jackson
$722Air France
Wed, Oct 28 - Wed, Nov 18
Delta Logo
6:00 am - 9:55 amMDW  Chicago Midway-MAD Madrid Barajas
20h 55m1 stop Atlanta Hartsfield-Jackson
Delta Logo
11:55 am - 10:56 pmMAD  Madrid Barajas-MDW Chicago Midway
18h 01m1 stop Atlanta Hartsfield-Jackson
$722Delta
Sun, Nov 29 - Thu, Dec 10
Delta Logo
10:35 am - 10:55 amMDW  Chicago Midway-MAD Madrid Barajas
17h 20m1 stop Atlanta Hartsfield-Jackson
Delta Logo
11:55 am - 10:10 pmMAD  Madrid Barajas-MDW Chicago Midway
17h 15m1 stop Atlanta Hartsfield-Jackson
$722Delta
Wed, Feb 10 - Wed, Feb 17
Delta Logo
11:28 am - 9:55 amMDW  Chicago Midway-MAD Madrid Barajas
15h 27m1 stop Atlanta Hartsfield-Jackson
Delta Logo
11:55 am - 10:56 pmMAD  Madrid Barajas-MDW Chicago Midway
18h 01m1 stop Atlanta Hartsfield-Jackson
$722Delta
Mon, Nov 9 - Thu, Nov 19
Delta Logo
1:00 pm - 9:55 amMDW  Chicago Midway-MAD Madrid Barajas
13h 55m1 stop Atlanta Hartsfield-Jackson
Delta Logo
11:55 am - 10:56 pmMAD  Madrid Barajas-MDW Chicago Midway
18h 01m1 stop Atlanta Hartsfield-Jackson
$722Delta
Mon, Nov 30 - Thu, Dec 10
Delta Logo
6:00 am - 9:45 amMDW  Chicago Midway-MAD Madrid Barajas
20h 45m1 stop Atlanta Hartsfield-Jackson
Delta Logo
12:20 pm - 10:56 pmMAD  Madrid Barajas-MDW Chicago Midway
17h 36m1 stop Atlanta Hartsfield-Jackson
$722Delta
Wed, Nov 25 - Fri, Dec 4
Delta Logo
1:00 pm - 9:45 amMDW  Chicago Midway-MAD Madrid Barajas
13h 45m1 stop Atlanta Hartsfield-Jackson
Delta Logo
12:20 pm - 10:56 pmMAD  Madrid Barajas-MDW Chicago Midway
17h 36m1 stop Atlanta Hartsfield-Jackson
$722Delta
Mon, Nov 23 - Fri, Dec 4
Delta Logo
11:28 am - 9:55 amMDW  Chicago Midway-MAD Madrid Barajas
15h 27m1 stop Atlanta Hartsfield-Jackson
Delta Logo
11:55 am - 10:56 pmMAD  Madrid Barajas-MDW Chicago Midway
18h 01m1 stop Atlanta Hartsfield-Jackson
$722Delta
Mon, Nov 9 - Tue, Nov 24

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KLM flights from Chicago Midway Airport to Madrid

Our best KLM deals on Chicago Midway Airport to Madrid flight tickets
KLM
Jan 20
MDW10:35 amChicago Midway
18h 10m
1 stop
MAD11:45 amMadrid Barajas
Jan 27
MAD6:05 amMadrid Barajas
17h 20m
2 stops
MDW4:25 pmChicago Midway
$717
KLM
Oct 27
MDW12:45 pmChicago Midway
15h 10m
1 stop
MAD9:55 amMadrid Barajas
Nov 17
MAD6:05 amMadrid Barajas
17h 09m
2 stops
MDW4:14 pmChicago Midway
$724
KLM
Sep 29
MDW5:11 pmChicago Midway
12h 04m
1 stop
MAD12:15 pmMadrid Barajas
Oct 6
MAD6:00 amMadrid Barajas
17h 47m
2 stops
MDW4:47 pmChicago Midway
$785

Virgin Atlantic flights from Chicago Midway Airport to Madrid

Our best Virgin Atlantic deals on Chicago Midway Airport to Madrid flight tickets
Virgin Atlantic
Nov 11
MDW1:22 pmChicago Midway
13h 33m
2 stops
MAD9:55 amMadrid Barajas
Nov 18
MAD10:00 amMadrid Barajas
19h 56m
2 stops
MDW10:56 pmChicago Midway
$846
Virgin Atlantic
Aug 16
MDW10:54 amChicago Midway
18h 21m
1 stop
MAD12:15 pmMadrid Barajas
Aug 25
MAD9:50 amMadrid Barajas
15h 43m
2 stops
MDW6:33 pmChicago Midway
$985
Virgin Atlantic
Aug 17
MDW5:10 pmChicago Midway
12h 05m
1 stop
MAD12:15 pmMadrid Barajas
Aug 25
MAD9:50 amMadrid Barajas
13h 25m
1 stop
MDW4:15 pmChicago Midway
$991

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 August 15, 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 Chicago Midway - MAD Madrid Barajas

MDWMAD

Chicago Midway

Mon 9/14

11:45 am-12:40 pm

2 stops17h 55m

Madrid Barajas

Mon 9/21

2:10 pm-11:00 am

2 stops27h 50m

$707

ChicagoMadrid

MDW Chicago Midway - MAD Madrid Barajas

MDWMAD

Chicago Midway

Wed 1/20

10:35 am-11:45 am

1 stop18h 10m

Madrid Barajas

Wed 1/27

6:05 am-4:25 pm

2 stops17h 20m

$717

ChicagoMadrid

MDW Chicago Midway - MAD Madrid Barajas

MDWMAD

Chicago Midway

Wed 10/28

12:45 pm-9:45 am

1 stop15h 00m

Madrid Barajas

Wed 11/18

12:20 pm-10:56 pm

1 stop17h 36m

$722

ChicagoMadrid

MDW Chicago Midway - MAD Madrid Barajas

MDWMAD

Chicago Midway

Sun 11/29

6:00 am-9:55 am

1 stop20h 55m

Madrid Barajas

Thu 12/10

11:55 am-10:56 pm

1 stop18h 01m

$722

ChicagoMadrid

MDW Chicago Midway - MAD Madrid Barajas

MDWMAD

Chicago Midway

Wed 2/10

10:35 am-10:55 am

1 stop17h 20m

Madrid Barajas

Wed 2/17

11:55 am-10:10 pm

1 stop17h 15m

$722

ChicagoMadrid

MDW Chicago Midway - MAD Madrid Barajas

MDWMAD

Chicago Midway

Mon 11/9

11:28 am-9:55 am

1 stop15h 27m

Madrid Barajas

Thu 11/19

11:55 am-10:56 pm

1 stop18h 01m

$722

ChicagoMadrid

MDW Chicago Midway - MAD Madrid Barajas

MDWMAD

Chicago Midway

Mon 11/30

1:00 pm-9:55 am

1 stop13h 55m

Madrid Barajas

Thu 12/10

11:55 am-10:56 pm

1 stop18h 01m

$722

ChicagoMadrid

MDW Chicago Midway - MAD Madrid Barajas

MDWMAD

Chicago Midway

Wed 11/25

6:00 am-9:45 am

1 stop20h 45m

Madrid Barajas

Fri 12/4

12:20 pm-10:56 pm

1 stop17h 36m

$722
Quickest round-trip

ChicagoMadrid

MDW Chicago Midway - MAD Madrid Barajas

MDWMAD

Chicago Midway

Mon 11/23

1:00 pm-9:45 am

1 stop13h 45m

Madrid Barajas

Fri 12/4

12:20 pm-10:56 pm

1 stop17h 36m

$722

ChicagoMadrid

MDW Chicago Midway - MAD Madrid Barajas

MDWMAD

Chicago Midway

Mon 11/9

11:28 am-9:55 am

1 stop15h 27m

Madrid Barajas

Tue 11/24

11:55 am-10:56 pm

1 stop18h 01m

$722

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 $790. 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 $946.

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 $861 when looking at flights departing in the afternoon. Flights to Madrid are more costly in the evening, with an average ticket price of $888. Departure times in the evening fall within the peak daily travel times, which is why tickets can be more expensive.

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

13h 55m

Direct flights

None
The fastest flight from Chicago Midway Airport to Madrid takes 13h 55m
There are no direct flights from Chicago Midway Airport to Madrid. There are no popular flight routes from Chicago Midway Airport to Madrid.
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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 13h 55m.

  • 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
Guadalajara
San Lorenzo de El Escorial

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 $832