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Cheap flights from Madrid to Chicago from $383

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 9/23. 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

Delta Logo
6:00 am - 6:25 pmMAD-MDW
19h 25m2 stops
Delta Logo
6:23 pm - 3:35 pmMDW-MAD
14h 12m2 stops
$606Delta
Find Deal
Thu, Oct 9 - Tue, Oct 14
Delta Logo
6:00 am - 6:25 pmMAD-MDW
19h 25m2 stops
Delta Logo
1:08 pm - 11:20 amMDW-MAD
15h 12m2 stops
$609Delta
Find Deal
Thu, Oct 9 - Mon, Oct 13
Delta Logo
6:00 am - 6:37 pmMAD-MDW
19h 37m2 stops
Delta Logo
12:43 pm - 9:35 amMDW-MAD
13h 52m1 stop
$610Delta
Find Deal
Mon, Sep 1 - Mon, Sep 15
Delta Logo
10:05 am - 10:14 pmMAD-MDW
19h 09m1 stop
Delta Logo
6:23 pm - 4:45 pmMDW-MAD
15h 22m2 stops
$611Delta
Find Deal
Thu, Oct 9 - Mon, Oct 13
Virgin Atlantic Logo
10:05 am - 9:26 pmMAD-MDW
18h 21m1 stop
Virgin Atlantic Logo
12:43 pm - 9:35 amMDW-MAD
13h 52m1 stop
$615Virgin Atlantic
Find Deal
Tue, Sep 9 - Mon, Sep 15
Virgin Atlantic Logo
12:40 pm - 10:14 pmMAD-MDW
16h 34m2 stops
Virgin Atlantic Logo
6:00 am - 9:35 amMDW-MAD
20h 35m1 stop
$640Virgin Atlantic
Find Deal
Thu, Oct 16 - Sun, Oct 19
Virgin Atlantic Logo
10:05 am - 5:51 pmMAD-MDW
14h 46m1 stop
Virgin Atlantic Logo
6:00 am - 9:35 amMDW-MAD
20h 35m1 stop
$656Virgin Atlantic
Find Deal
Fri, Sep 26 - Sat, Oct 4
KLM Logo
10:05 am - 10:14 pmMAD-MDW
19h 09m1 stop
KLM Logo
12:48 pm - 9:35 amMDW-MAD
13h 47m1 stop
$689KLM
Find Deal
Thu, Oct 9 - Mon, Oct 13
KLM Logo
10:05 am - 5:35 pmMAD-MDW
14h 30m1 stop
KLM Logo
12:48 pm - 9:35 amMDW-MAD
13h 47m1 stop
$712KLM
Find Deal
Wed, Oct 1 - Tue, Oct 7
KLM Logo
10:05 am - 10:14 pmMAD-MDW
19h 09m1 stop
KLM Logo
12:48 pm - 9:35 amMDW-MAD
13h 47m1 stop
$756KLM
Find Deal
Thu, Oct 9 - Mon, Oct 13

Delta flights from Madrid to Chicago Midway Airport

Our best Delta deals on Madrid to Chicago Midway Airport flight tickets
Delta
Oct 9
MAD6:00 amMadrid Barajas
19h 25m
2 stops
MDW6:25 pmChicago Midway
Oct 14
MDW6:23 pmChicago Midway
14h 12m
2 stops
MAD3:35 pmMadrid Barajas
$606
Find similar
Delta
Oct 9
MAD6:00 amMadrid Barajas
19h 25m
2 stops
MDW6:25 pmChicago Midway
Oct 13
MDW1:08 pmChicago Midway
15h 12m
2 stops
MAD11:20 amMadrid Barajas
$609
Find similar
Delta
Sep 1
MAD6:00 amMadrid Barajas
19h 37m
2 stops
MDW6:37 pmChicago Midway
Sep 15
MDW12:43 pmChicago Midway
13h 52m
1 stop
MAD9:35 amMadrid Barajas
$610
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
Sep 9
MAD10:05 amMadrid Barajas
18h 21m
1 stop
MDW9:26 pmChicago Midway
Sep 15
MDW12:43 pmChicago Midway
13h 52m
1 stop
MAD9:35 amMadrid Barajas
$615
Find similar
Virgin Atlantic
Oct 16
MAD12:40 pmMadrid Barajas
16h 34m
2 stops
MDW10:14 pmChicago Midway
Oct 19
MDW6:00 amChicago Midway
20h 35m
1 stop
MAD9:35 amMadrid Barajas
$640
Find similar
Virgin Atlantic
Sep 26
MAD10:05 amMadrid Barajas
14h 46m
1 stop
MDW5:51 pmChicago Midway
Oct 4
MDW6:00 amChicago Midway
20h 35m
1 stop
MAD9:35 amMadrid Barajas
$656
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 July 31, 2025.
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

Thu 10/9

6:00 am-6:25 pm

2 stops19h 25m

Chicago Midway

Tue 10/14

6:23 pm-3:35 pm

2 stops14h 12m

$606

MadridChicago

MAD - MDW

MADMDW

Madrid Barajas

Thu 10/9

6:00 am-6:25 pm

2 stops19h 25m

Chicago Midway

Mon 10/13

1:08 pm-11:20 am

2 stops15h 12m

$609

MadridChicago

MAD - MDW

MADMDW

Madrid Barajas

Mon 9/1

6:00 am-6:37 pm

2 stops19h 37m

Chicago Midway

Mon 9/15

12:43 pm-9:35 am

1 stop13h 52m

$610

MadridChicago

MAD - MDW

MADMDW

Madrid Barajas

Thu 10/9

10:05 am-10:14 pm

1 stop19h 09m

Chicago Midway

Mon 10/13

6:23 pm-4:45 pm

2 stops15h 22m

$611

MadridChicago

MAD - MDW

MADMDW

Madrid Barajas

Tue 9/9

10:05 am-9:26 pm

1 stop18h 21m

Chicago Midway

Mon 9/15

12:43 pm-9:35 am

1 stop13h 52m

$615

MadridChicago

MAD - MDW

MADMDW

Madrid Barajas

Thu 10/16

12:40 pm-10:14 pm

2 stops16h 34m

Chicago Midway

Sun 10/19

6:00 am-9:35 am

1 stop20h 35m

$640

MadridChicago

MAD - MDW

MADMDW

Madrid Barajas

Fri 9/26

10:05 am-5:51 pm

1 stop14h 46m

Chicago Midway

Sat 10/4

6:00 am-9:35 am

1 stop20h 35m

$656

MadridChicago

MAD - MDW

MADMDW

Madrid Barajas

Thu 10/9

10:05 am-10:14 pm

1 stop19h 09m

Chicago Midway

Mon 10/13

12:48 pm-9:35 am

1 stop13h 47m

$689

MadridChicago

MAD - MDW

MADMDW

Madrid Barajas

Wed 10/1

10:05 am-5:35 pm

1 stop14h 30m

Chicago Midway

Tue 10/7

12:48 pm-9:35 am

1 stop13h 47m

$712

MadridChicago

MAD - MDW

MADMDW

Madrid Barajas

Thu 10/9

10:05 am-10:14 pm

1 stop19h 09m

Chicago Midway

Mon 10/13

12:48 pm-9:35 am

1 stop13h 47m

$756

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 Chicago from

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

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 airline that flies from Madrid Barajas to Chicago Midway?

Delta and Virgin Atlantic are the most popular carriers operating from Madrid Barajas to Chicago Midway

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

Best Price Found

$383

Fastest flight time

14h 30m

Direct flights

None
The best one-way flight to Chicago Midway Airport from Madrid in the past 72 hours is $383. The best round-trip flight deal from Madrid to Chicago Midway Airport found on momondo in the last 72 hours is $606.
The fastest flight from Madrid to Chicago Midway Airport takes 14h 30m
There are no direct flights from Madrid to Chicago Midway Airport. Popular non-direct route for this connection is Madrid Barajas Airport - 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. 14h 30m 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.

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
Crown Point
Munster
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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