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$176+ Cheap flights from Chicago (CHI) to Madrid, Spain (MAD)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/7. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MAD
Aug 4 — Aug 111
Mon 8/4
Mon 8/11
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Madrid Barajas are usually found in February or January, booked 67 days in advance, depart on a Wednesday or Monday and return on a Monday

Cheap flight deals from Chicago to Madrid

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Madrid (MAD). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated July 30, 2025.

Round-trip from

$323
(oojo)

One-way from

$174
(Cheapflightsfares)

Popular in

June

Cheapest in

February

Average price

$818

Good round-trip deal

$505 or less

Good one-way deal

$478 or less
From Chicago (CHI) to Madrid Barajas
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One-way flight from Chicago (CHI) to Madrid Barajas
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Highest demand for flights based on searches. 21% potential increase in price ($188 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($26 potential savings vs. average RT price).
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Average for round-trip flights in July 2025
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Price to beat on a round-trip flight from Chicago (CHI) to Madrid Barajas.
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Price to beat on a one-way flight from Chicago (CHI) to Madrid Barajas.
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Find flight deals from Chicago to Madrid

Cheapest flights from Chicago to Madrid
Explore the most affordable flight options available from Chicago to Madrid. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 30, 2025.

This oojo deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/127:10 pmORD - MAD
1 stop11h 55mTAP AIR PORTUGAL
Thu 11/209:10 pmMAD - ORD
1 stop25h 05mTAP AIR PORTUGAL
Deal found 7/28$323
This United Airlines deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/312:50 pmORD - MAD
1 stop12h 10mUnited Airlines
Thu 12/111:35 pmMAD - ORD
2 stops41h 09mUnited Airlines
Deal found 7/28$341
This Booking.com deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/283:35 pmORD - MAD
1 stop32h 05mAir Canada
Thu 10/96:20 amMAD - ORD
2 stops21h 02mAir Canada
Deal found 7/28$342
This lol.travel deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/1811:46 amORD - MAD
1 stop14h 39mFinnair
Tue 11/2511:35 amMAD - ORD
Nonstop9h 55mFinnair
Deal found 7/30$343
This Cheapflightsfares deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/71:43 pmORD - MAD
1 stop11h 32mIberia
Tue 10/144:40 pmMAD - ORD
Nonstop9h 10mIberia
Deal found 7/30$350
This KLM deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/31:05 pmMDW - MAD
1 stop12h 55mKLM
Wed 12/1011:00 amMAD - MDW
1 stop17h 44mKLM
Deal found 7/28$359
This American Airlines deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/2210:30 pmORD - MAD
Nonstop7h 55mAmerican Airlines
Wed 10/112:40 pmMAD - ORD
1 stop13h 53mAmerican Airlines
Deal found 7/30$361
This Delta deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/31:05 pmMDW - MAD
1 stop12h 55mDelta
Wed 12/1011:00 amMAD - MDW
1 stop17h 44mDelta
Deal found 7/28$368
This Booking.com deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/228:40 amORD - MAD
2 stops16h 40mMultiple Airlines
Wed 11/57:35 pmMAD - ORD
1 stop27h 45mMultiple Airlines
Deal found 7/28$374
This Virgin Atlantic deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Virgin Atlantic is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/11:05 pmMDW - MAD
1 stop12h 55mVirgin Atlantic
Sun 12/1411:00 amMAD - MDW
1 stop17h 44mVirgin Atlantic
Deal found 7/30$418
This flugladen.de deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure flugladen.de is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/176:04 amMDW - MAD
1 stop20h 31mMultiple Airlines
Tue 8/268:15 pmMAD - MDW
2 stops29h 22mMultiple Airlines
Deal found 7/28$507

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago 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, Cheapflights users made 2,558,603 searches. Data last updated July 30, 2025.
Use the filters below to find and compare flights from Chicago to Madrid that are best for you.

Fly from

Chicago

Fly to

Madrid

Route

Depart

Return

Price

ChicagoMadrid

ORD - MAD

ORDMAD

Chicago O'Hare Intl

Mon 8/11

6:10 pm-12:40 pm

1 stop11h 30m

Madrid Barajas

Wed 8/27

8:10 pm-12:50 pm

1 stop23h 40m

$325

ChicagoMadrid

ORD - MAD

ORDMAD

Chicago O'Hare Intl

Sun 9/28

3:35 pm-6:40 am

1 stop32h 05m

Madrid Barajas

Thu 10/9

6:20 am-8:22 pm

2 stops21h 02m

$342

ChicagoMadrid

ORD - MAD

ORDMAD

Chicago O'Hare Intl

Mon 10/27

6:20 pm-8:05 am

1 stop31h 45m

Madrid Barajas

Fri 11/14

1:35 pm-2:55 pm

1 stop32h 20m

$346

ChicagoMadrid

ORD - MAD

ORDMAD

Chicago O'Hare Intl

Tue 10/28

5:45 pm-7:55 am

Nonstop8h 10m

Madrid Barajas

Tue 11/11

11:35 am-2:30 pm

Nonstop9h 55m

$349

ChicagoMadrid

ORD - MAD

ORDMAD

Chicago O'Hare Intl

Tue 10/7

1:43 pm-8:15 am

1 stop11h 32m

Madrid Barajas

Tue 10/14

4:40 pm-6:50 pm

Nonstop9h 10m

$350

ChicagoMadrid

ORD - MAD

ORDMAD

Chicago O'Hare Intl

Mon 9/22

10:30 pm-1:25 pm

Nonstop7h 55m

Madrid Barajas

Wed 10/1

12:40 pm-7:33 pm

1 stop13h 53m

$361

ChicagoMadrid

MDW - MAD

MDWMAD

Chicago Midway

Mon 8/18

12:43 pm-9:35 am

1 stop13h 52m

Madrid Barajas

Tue 9/16

10:05 am-9:36 pm

1 stop18h 31m

$368

ChicagoMadrid

MDW - MAD

MDWMAD

Chicago Midway

Tue 8/19

12:43 pm-9:35 am

1 stop13h 52m

Madrid Barajas

Tue 9/16

10:05 am-6:35 pm

2 stops15h 30m

$373

ChicagoMadrid

ORD - MAD

ORDMAD

Chicago O'Hare Intl

Wed 10/22

8:40 am-8:20 am

2 stops16h 40m

Madrid Barajas

Wed 11/5

7:35 pm-4:20 pm

1 stop27h 45m

$374

ChicagoMadrid

ORD - MAD

ORDMAD

Chicago O'Hare Intl

Wed 10/8

1:08 pm-7:50 am

1 stop11h 42m

Madrid Barajas

Tue 10/21

6:00 am-2:10 pm

1 stop15h 10m

$384

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/28

Showing 1-10 of 21 results
1
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The best insider tips for Chicago to Madrid flights

Snippets provided in this section are AI-generated based on a summarization of Cheapflights-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
Cheapflights partnered with top experts to bring you the best recommendations for your Chicago to Madrid trip
Airports
ORD

For a smooth departure from ORD, consider using the 'L' train to avoid traffic delays. It's a reliable option from downtown Chicago.

Read more about ORDby Ramsey Qubein
MAD

Upon arrival at MAD, use the Express Airport Bus for a quick ride to central spots like Atocha and Cibeles.

Read more about MADby Lori Zaino
Our travel experts
Ramsey Qubein

Ramsey Qubein

Expert on ORD

Ramsey Qubein

Ramsey Qubein

An avid traveler and aviation expert who has visited 173 countries, all 50 states and seven continents, Ramsey Qubein flies nearly 400,000 miles a year. As a North Carolina-based freelance journalist for publications including Conde Nast Traveler, Forbes, USA Today and Bloomberg among others, he explores the latest trends in aviation, hospitality, cruises and business.

Read more
Lori Zaino

Lori Zaino

Expert on MAD

Lori Zaino

Lori Zaino

US-born but now based in Spain, Lori's visited 60 countries---and written about them for publications like CNN, Forbes, The Points Guy, NBC, and TripAdvisor. She loves combining affordable adventures with luxury travel experiences and feels equally at home salsa dancing in Colombia, sipping wine in a French castle, or backpacking through Malaysia.

Read more

Best time to book a flight from Chicago to Madrid

Have a flexible travel schedule? Discover the best time to fly to Madrid from Chicago with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chicago to Madrid

How far ahead should I book a flight from Chicago to Madrid?

Use this chart to determine the optimal time to book a round-trip flight from Chicago to Madrid. Price data was last updated on July 25, 2025.

The price you pay for your flight from Chicago to Madrid may vary depending on when you book. For the best chance of a lower fare, look to book 67 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

What is the cheapest month to book a flight from Chicago to Madrid?

Currently, November is the cheapest month in which you can book a flight from Chicago to Madrid (average of $543). Flying from Chicago to Madrid in June is currently the most expensive (average of $1,052). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from CHI to MAD?

Find hourly flight availability from Chicago to Madrid. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated July 30, 2025.

When flying from Chicago to Madrid, the time of day you fly usually plays a role in the price. Save by searching for a flight in the afternoon, which can drop the price by up to 15% versus a flight in the evening.

What is the cheapest day to fly from Chicago to Madrid?

Use this chart to determine the cheapest time to fly round-trip from Chicago to Madrid. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Chicago to Madrid flight should consider departing on Wednesday mornings when fares are most often at their lowest. Saturday evenings flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Chicago to Madrid

Explore weekly flight availability from Chicago to Madrid. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated July 30, 2025.

The most flights from CHI to MAD are scheduled on a Monday (11 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (5 on average).

How much does it cost to fly round-trip from Chicago to Madrid?

What’s the top layover airport for flights from Chicago to Madrid?

Share of 1-stop round-trip flights from Chicago to Madrid chosen by Cheapflights users in the past 12 months, using the same layover each way.

Lisbon (LIS) – chosen by Cheapflights users on 73% of 1-stop itineraries from Chicago to Madrid on Cheapflights.

What’s the cheapest layover airport for flights from Chicago to Madrid?

Average round-trip fare for 1-stop flights from Chicago to Madrid, chosen by Cheapflights users in the past 12 months, with the same layover each way.

Lisbon (LIS) is the most affordable 1-stop option, with an average round-trip price of $350.

What’s the fastest layover option from Chicago to Madrid?

Shortest average travel time for 1-stop one-way flights from Chicago to Madrid, based on itineraries clicked by Cheapflights users over the past 12 months, grouped by layover airport.

Flights via Paris (CDG) have the shortest average one-way travel time for 1-stop routes: 3h 15m.

Which airport typically offers the quickest layover for flights from Chicago to Madrid?

Average layover duration for 1-stop one-way flights from Chicago to Madrid, chosen by Cheapflights users in the last 12 months, grouped by stopover airport.

Flights via Paris (CDG) offer the fastest connection on this route, with an average layover time of 1h 05m.

Reviews of airlines servicing Madrid

Get insights into the airlines that provide service to Madrid. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Madrid. Reviews last updated July 30, 2025.
Peruse reviews from past customers who have flown with Delta, KLM, and Finnair from Chicago to Madrid to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,980 reviews

Entertainment

7.9

Food

7.3

Overall

8.0

Crew

8.5

Boarding

8.2

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,980 reviews
Delta
8.0
Very good
7,980 reviews

Entertainment

7.9

Food

7.3

Overall

8.0

Crew

8.5

Boarding

8.2

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
KLM
7.8
Good
1,383 reviews
Delta
8.0
Very good
7,980 reviews

Entertainment

7.9

Food

7.3

Overall

8.0

Crew

8.5

Boarding

8.2

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Finnair
7.6
Good
1,316 reviews
Delta
8.0
Very good
7,980 reviews

Entertainment

7.9

Food

7.3

Overall

8.0

Crew

8.5

Boarding

8.2

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Air France
7.5
Good
1,465 reviews
Delta
8.0
Very good
7,980 reviews

Entertainment

7.9

Food

7.3

Overall

8.0

Crew

8.5

Boarding

8.2

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
United Airlines
7.4
Good
8,896 reviews
Delta
8.0
Very good
7,980 reviews

Entertainment

7.9

Food

7.3

Overall

8.0

Crew

8.5

Boarding

8.2

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

Related info for your journey

Find useful and relevant information for your journey from Chicago to Madrid. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Madrid from Chicago?

    If you book a flight to Madrid from Chicago, you will be flying to Barajas, which is the city’s only airport. Madrid Barajas (MAD) is located 8.5 mi from the center of Madrid. There are 10 flights from Chicago to Barajas per day from 17 different airlines.

  • What are the cheapest airlines flying from Chicago to Madrid round-trip?

    TAP AIR PORTUGAL, at $323, was found to be the cheapest airline from Chicago to Madrid.Alternate airlines to your destination round-trip include United Airlines and Air Canada. You may be able to fly from Chicago to Madrid for 53% less than the average price by searching for these airlines.

  • What are the cheapest airlines to fly from Chicago to Madrid one-way?

    The cheapest airline one-way is TAP AIR PORTUGAL, with whom users have recently found tickets for as low as $174. However, be on the lookout for offers from KLM and Delta, as they are both options that can get you from Chicago to Madrid for a low price.

  • What are the most reliable airlines from Chicago to Madrid?

    Consider American Airlines (60%), Finnair (60%) or Iberia (60%) when booking your flight. These represent the most reliable airlines when flying from Chicago to Madrid.

  • What are the cheapest flights from Chicago to Madrid?

    Looking for the cheapest flight from Chicago to Madrid? While on average our users pay $1,513, our data indicates the cheapest price to be $353. The most popular route (Chicago O'Hare Intl - Madrid Barajas), is priced around $319.

  • Where are the most common layover locations when flying from Chicago to Madrid?

    Most of the time, Chicago to Madrid flights that have layovers will stop in Lisbon. New York is the second most popular location for layovers on flights from Chicago to Madrid.

  • What are some popular things to do or see while on a layover in Lisbon?

    Chiado, Praça do Marquês de Pombal, and Londres are currently the most popular points of interest in Lisbon at the moment. Chiado, Praça do Marquês de Pombal and Londres are located about 4.5 mi, 3.6 mi, and 2.3 mi, respectively from Lisbon Humberto Delgado if you are interested in checking them out. Travelers can book a car rental at Lisbon Humberto Delgado for about $27 per day to make their sightseeing more efficient.

  • What are some popular points of interest to see during a layover in New York?

    Most New York visitors opt to spend their time at Times Square, New York City Center, and Madison Square Garden. Times Square, New York City Center, and Madison Square Garden can be visited by traveling about 13.6 mi, 13.6 mi, and 13.6 mi respectively from New York John F Kennedy Intl. Those on a layover in New York in need of a rental car can book one at New York John F Kennedy Intl for about $84.

  • Where are the least popular layover locations for Chicago to Madrid flights?

    Flights departing from Chicago and landing in Madrid layover in London least frequently.

  • Can I find deals for flights from Chicago to Madrid that include hotel bookings?

    Yes. In addition to deals on Chicago to Madrid flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Madrid?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Madrid.

  • Can I find deals for business class flights from Chicago to Madrid?

    Yes. Cheapflights offers flight deals from Chicago to Madrid by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago to Madrid?

    Currently, November is the cheapest month in which you can book a flight from Chicago to Madrid (average of $543). Flying from Chicago to Madrid in June is currently the most expensive (average of $1,052). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Madrid?

Book flights to Madrid if you plan to visit one of these locations
Segovia
Fuenlabrada

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Alternative routes for Chicago to Madrid

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Madrid flights
Midway to Madrid flights
St. Louis to Madrid flights

Top 10 airlines flying from Chicago to Madrid

Discover the top 10 airlines that operate flights from Chicago to Madrid. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated July 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$120Average$203FlexibilityNo cancel feeOn-time62%
TAP AIR PORTUGALCheapest$288Average$523FlexibilityNo cancel feeOn-timeN/A
Air CanadaCheapest$366Average$646FlexibilityNo cancel feeOn-time67%
Scandinavian AirlinesCheapest$387Average$462FlexibilityNo cancel feeOn-time77%
FinnairCheapest$405Average$624FlexibilityNo cancel feeOn-time76%
DeltaCheapest$455Average$887FlexibilityNo cancel feeOn-timeN/A
IberiaCheapest$463Average$753FlexibilityNo cancel feeOn-time77%
United AirlinesCheapest$471Average$711FlexibilityNo cancel feeOn-time69%
British AirwaysCheapest$471Average$647FlexibilityNo cancel feeOn-time70%
Aer LingusCheapest$484Average$741FlexibilityNo cancel feeOn-timeN/A

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