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Cheap flights from Madrid to Chicago from $363

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Madrid to Chicago departing on 2/19. 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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Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
6:00 am - 5:54 pm
MAD
-
MDW
18h 54m2 stops
Delta Logo
5:31 pm - 12:15 pm
MDW
-
MAD
11h 44m1 stop
$483Delta
Sat, Apr 18 - Sat, Apr 25
Delta Logo
6:00 am - 5:54 pm
MAD
-
MDW
18h 54m2 stops
Delta Logo
5:31 pm - 12:15 pm
MDW
-
MAD
11h 44m1 stop
$484Delta
Sat, Apr 18 - Sat, Apr 25
Delta Logo
6:00 am - 4:16 pm
MAD
-
MDW
17h 16m2 stops
Delta Logo
10:48 am - 9:15 am
MDW
-
MAD
15h 27m1 stop
$485Delta
Sat, Jan 24 - Fri, Feb 6
Multiple Airlines Logo
11:15 am - 10:22 pm
MAD
-
MDW
18h 07m1 stop
Multiple Airlines Logo
11:45 am - 11:30 am
MDW
-
MAD
16h 45m2 stops
$486Multiple Airlines
Sat, Jan 31 - Sat, Feb 7
Delta Logo
6:00 am - 6:40 pm
MAD
-
MDW
18h 40m2 stops
Delta Logo
1:10 pm - 10:15 am
MDW
-
MAD
15h 05m2 stops
$487Delta
Thu, Mar 12 - Sun, Mar 15
Delta Logo
12:40 pm - 10:29 pm
MAD
-
MDW
16h 49m1 stop
Delta Logo
5:31 pm - 12:15 pm
MDW
-
MAD
11h 44m1 stop
$489Delta
Sat, Apr 18 - Sat, Apr 25
Virgin Atlantic Logo
12:40 pm - 10:29 pm
MAD
-
MDW
16h 49m1 stop
Virgin Atlantic Logo
5:31 pm - 12:15 pm
MDW
-
MAD
11h 44m1 stop
$490Virgin Atlantic
Thu, Apr 16 - Sun, Apr 19
Delta Logo
10:05 am - 10:31 pm
MAD
-
MDW
18h 26m1 stop
Delta Logo
1:10 pm - 10:15 am
MDW
-
MAD
15h 05m2 stops
$492Delta
Thu, Mar 12 - Sun, Mar 15
Multiple Airlines Logo
11:15 am - 10:07 pm
MAD
-
MDW
17h 52m1 stop
Multiple Airlines Logo
6:14 pm - 3:20 pm
MDW
-
MAD
14h 06m2 stops
$494Multiple Airlines
Thu, Jan 15 - Sun, Jan 18
KLM Logo
11:15 am - 10:31 pm
MAD
-
MDW
18h 16m1 stop
KLM Logo
12:45 pm - 9:15 am
MDW
-
MAD
13h 30m1 stop
$498KLM
Thu, Feb 19 - Sun, Feb 22

Delta flights from Madrid to Chicago Midway Airport

Our best Delta deals on Madrid to Chicago Midway Airport flight tickets
Delta
Apr 18
MAD6:00 amMadrid Barajas
18h 54m
2 stops
MDW5:54 pmChicago Midway
Apr 25
MDW5:31 pmChicago Midway
11h 44m
1 stop
MAD12:15 pmMadrid Barajas
$483
Find similar
Delta
Apr 18
MAD6:00 amMadrid Barajas
18h 54m
2 stops
MDW5:54 pmChicago Midway
Apr 25
MDW5:31 pmChicago Midway
11h 44m
1 stop
MAD12:15 pmMadrid Barajas
$484
Find similar
Delta
Jan 24
MAD6:00 amMadrid Barajas
17h 16m
2 stops
MDW4:16 pmChicago Midway
Feb 6
MDW10:48 amChicago Midway
15h 27m
1 stop
MAD9:15 amMadrid Barajas
$485
Find similar

Virgin Atlantic flights from Madrid to Chicago Midway Airport

Our best Virgin Atlantic deals on Madrid to Chicago Midway Airport flight tickets
Virgin Atlantic
Apr 16
MAD12:40 pmMadrid Barajas
16h 49m
1 stop
MDW10:29 pmChicago Midway
Apr 19
MDW5:31 pmChicago Midway
11h 44m
1 stop
MAD12:15 pmMadrid Barajas
$490
Find similar
Virgin Atlantic
Mar 6
MAD11:15 amMadrid Barajas
13h 30m
1 stop
MDW5:45 pmChicago Midway
Mar 9
MDW12:47 pmChicago Midway
13h 18m
1 stop
MAD8:05 amMadrid Barajas
$530
Find similar
Virgin Atlantic
Apr 23
MAD12:40 pmMadrid Barajas
16h 49m
1 stop
MDW10:29 pmChicago Midway
Apr 26
MDW12:55 pmChicago Midway
16h 20m
1 stop
MAD12:15 pmMadrid Barajas
$559
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Madrid to Chicago Midway Airport 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 January 5, 2026.
Use the filters below to find and compare flights from Madrid to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

MadridChicago

MAD - MDW

MADMDW

Madrid Barajas

Sat 4/18

6:00 am-5:54 pm

2 stops18h 54m

Chicago Midway

Sat 4/25

5:31 pm-12:15 pm

1 stop11h 44m

$483

MadridChicago

MAD - MDW

MADMDW

Madrid Barajas

Sat 4/18

6:00 am-5:54 pm

2 stops18h 54m

Chicago Midway

Sat 4/25

5:31 pm-12:15 pm

1 stop11h 44m

$484

MadridChicago

MAD - MDW

MADMDW

Madrid Barajas

Sat 1/24

6:00 am-4:16 pm

2 stops17h 16m

Chicago Midway

Fri 2/6

10:48 am-9:15 am

1 stop15h 27m

$485

MadridChicago

MAD - MDW

MADMDW

Madrid Barajas

Sat 1/31

11:15 am-10:22 pm

1 stop18h 07m

Chicago Midway

Sat 2/7

11:45 am-11:30 am

2 stops16h 45m

$486

MadridChicago

MAD - MDW

MADMDW

Madrid Barajas

Thu 3/12

6:00 am-6:40 pm

2 stops18h 40m

Chicago Midway

Sun 3/15

1:10 pm-10:15 am

2 stops15h 05m

$487

MadridChicago

MAD - MDW

MADMDW

Madrid Barajas

Sat 4/18

12:40 pm-10:29 pm

1 stop16h 49m

Chicago Midway

Sat 4/25

5:31 pm-12:15 pm

1 stop11h 44m

$489

MadridChicago

MAD - MDW

MADMDW

Madrid Barajas

Thu 4/16

12:40 pm-10:29 pm

1 stop16h 49m

Chicago Midway

Sun 4/19

5:31 pm-12:15 pm

1 stop11h 44m

$490

MadridChicago

MAD - MDW

MADMDW

Madrid Barajas

Thu 3/12

10:05 am-10:31 pm

1 stop18h 26m

Chicago Midway

Sun 3/15

1:10 pm-10:15 am

2 stops15h 05m

$492

MadridChicago

MAD - MDW

MADMDW

Madrid Barajas

Thu 1/15

11:15 am-10:07 pm

1 stop17h 52m

Chicago Midway

Sun 1/18

6:14 pm-3:20 pm

2 stops14h 06m

$494

MadridChicago

MAD - MDW

MADMDW

Madrid Barajas

Thu 2/19

11:15 am-10:31 pm

1 stop18h 16m

Chicago Midway

Sun 2/22

12:45 pm-9:15 am

1 stop13h 30m

$498

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

When to book flights from Madrid to Chicago Midway Airport

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

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

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

Fastest flight time

17h 54m

Direct flights

None
The fastest flight from Madrid to Chicago Midway Airport takes 17h 54m
There are no direct flights from Madrid to Chicago Midway Airport. There are no popular flight routes from Madrid to Chicago Midway Airport.
Search flight deals

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

    There are 4184.0 mi between Madrid Barajas and Chicago Midway. 17h 54m is a normal flight duration for this route.

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

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

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

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Madrid Barajas Airport to Chicago Midway Airport.

  • What documentation or ID do you need to fly to Chicago Midway Airport?

    The travel and health documents required for your trip to Chicago Midway Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago Midway Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

  • How do I get Price Alerts for flights from Madrid to Chicago Midway Airport?

    You can take advantage of momondo’s Price Alerts by first searching for your flights to Madrid from Chicago Midway Airport. Flight offers will be shown to you in real-time. From there you can create a Price Alert by using our on-site widget.

  • How can I save money on flights from Madrid to Chicago Midway Airport with momondo?

    Plan your trips smart with the “Price Forecast” feature, which uses flight data to help you pick the best days to fly for the lowest fares. Our “Price Calendar” helps you get the most for your money by showing you when it’s most advantageous to fly. Curate your own travel experiences for less with “Explore”. Expert travel hacks to fuel your next adventure are a click away with “Discover” by momondo. Set up our “Price Alerts” to track fare changes and book when prices are at their lowest point.

  • How does momondo find its flight prices?

    We aggregate our prices from over 700+ competitors from airlines to OTAs. We operate in over 30 markets worldwide to show you a wide range of travel options.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Portage
Lansing
Schererville
Valparaiso
Munster
Crown Point
Chesterton
Monticello
Porter
Griffith
Saint John

Why use momondo?

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

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Madrid to Chicago for you.

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

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

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

Once you have performed a search for Madrid to Chicago flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

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

If you are not ready to book a flight from Madrid to Chicago now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Chicago and let you know when they change.

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