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$218+ 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 1/11. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MAD
dic. 6 — dic. 131
sáb. 12/6
sáb. 12/13
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

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 noviembre 6, 2025.

This Delta deal was found by Cheapflights users on 11/6. 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.
lun. 11/179:51 amORD - MAD
1 stop16h 24mDelta
mié. 12/36:00 amMAD - ORD
1 stop16h 10mDelta
Deal found 11/6$447
This Mytrip deal was found by Cheapflights users on 11/5. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 12/37:05 amORD - MAD
1 stop17h 55mAir Canada
mié. 12/106:25 amMAD - ORD
2 stops15h 30mAir Canada
Deal found 11/5$451
This Mytrip deal was found by Cheapflights users on 11/6. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 11/172:00 pmORD - MAD
2 stops14h 00mAir Canada
mié. 12/36:25 amMAD - ORD
2 stops15h 30mAir Canada
Deal found 11/6$452
This Delta deal was found by Cheapflights users on 11/6. 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.
mar. 11/185:23 amORD - MAD
1 stop20h 52mDelta
mar. 12/21:05 pmMAD - ORD
1 stop32h 15mDelta
Deal found 11/6$453
This Mytrip deal was found by Cheapflights users on 11/6. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 11/177:05 amORD - MAD
1 stop20h 55mMultiple Airlines
mié. 12/36:25 amMAD - ORD
2 stops15h 30mMultiple Airlines
Deal found 11/6$455
This Gotogate deal was found by Cheapflights users on 11/5. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 11/179:50 pmORD - MAD
1 stop18h 45mMultiple Airlines
mié. 11/265:55 amMAD - ORD
2 stops16h 00mMultiple Airlines
Deal found 11/5$456
This Delta deal was found by Cheapflights users on 11/6. 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.
mar. 11/1810:35 amORD - MAD
2 stops17h 55mDelta
jue. 12/411:15 amMAD - ORD
1 stop19h 46mDelta
Deal found 11/6$457
This Gurufare deal was found by Cheapflights users on 11/4. 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 Gurufare is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 11/1010:29 amORD - MAD
1 stop12h 16mBritish Airways
jue. 11/2011:35 amMAD - ORD
Nonstop9h 55mBritish Airways
Deal found 11/4$458
This Delta deal was found by Cheapflights users on 11/6. 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.
lun. 11/176:45 amORD - MAD
2 stops18h 15mDelta
mar. 12/211:00 amMAD - ORD
1 stop34h 20mDelta
Deal found 11/6$460
This United Airlines deal was found by Cheapflights users on 11/4. 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.
sáb. 11/2911:59 pmORD - MAD
1 stop25h 06mUnited Airlines
mié. 12/101:35 pmMAD - ORD
1 stop25h 25mUnited Airlines
Deal found 11/4$461
This Delta deal was found by Cheapflights users on 11/4. 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.
dom. 12/710:49 amMDW - MAD
1 stop15h 26mDelta
mar. 12/166:00 amMAD - MDW
2 stops19h 00mDelta
Deal found 11/4$462
This Delta deal was found by Cheapflights users on 11/5. 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.
mié. 11/267:00 amORD - MAD
1 stop18h 00mDelta
vie. 12/126:00 amMAD - ORD
2 stops19h 27mDelta
Deal found 11/5$462

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 noviembre 6, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$447
(Delta)

One-way from

$218
(Air France)

Popular in

December

Cheapest in

February

Average price

$629

Good round-trip deal

$656 or less

Good one-way deal

$478 or less
Provider with most accurate pricing for Chicago (CHI)-Madrid Barajas flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Madrid Barajas flights.
Search Deals
From Chicago (CHI) to Madrid Barajas
Search Deals
One-way flight from Chicago (CHI) to Madrid Barajas
Search Deals
Highest demand for flights based on searches. 3% potential increase in price ($26 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($27 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
Search Deals
Price to beat on a round-trip flight from Chicago (CHI) to Madrid Barajas.
Search Deals
Price to beat on a one-way flight from Chicago (CHI) to Madrid Barajas.
Search Deals

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 noviembre 6, 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

dom. 2/1

8:25 pm-8:20 pm

1 stop16h 55m

Madrid Barajas

dom. 2/8

7:40 am-2:45 pm

1 stop14h 05m

$460

ChicagoMadrid

ORD - MAD

ORDMAD

Chicago O'Hare Intl

dom. 2/1

5:10 pm-12:40 pm

1 stop12h 30m

Madrid Barajas

dom. 2/8

12:00 pm-2:55 pm

Nonstop9h 55m

$470

ChicagoMadrid

ORD - MAD

ORDMAD

Chicago O'Hare Intl

mié. 11/12

3:50 pm-4:05 pm

2 stops17h 15m

Madrid Barajas

jue. 11/20

11:15 am-9:56 pm

1 stop17h 41m

$470

ChicagoMadrid

ORD - MAD

ORDMAD

Chicago O'Hare Intl

vie. 1/2

5:40 pm-8:50 am

Nonstop8h 10m

Madrid Barajas

mié. 1/14

12:00 pm-2:55 pm

Nonstop9h 55m

$473

ChicagoMadrid

ORD - MAD

ORDMAD

Chicago O'Hare Intl

dom. 11/23

2:50 pm-8:55 am

1 stop11h 05m

Madrid Barajas

dom. 12/7

12:00 pm-2:55 pm

Nonstop9h 55m

$478

ChicagoMadrid

ORD - MAD

ORDMAD

Chicago O'Hare Intl

dom. 2/1

2:50 pm-8:55 am

1 stop11h 05m

Madrid Barajas

dom. 2/8

12:40 pm-7:50 pm

1 stop14h 10m

$479

ChicagoMadrid

ORD - MAD

ORDMAD

Chicago O'Hare Intl

mar. 11/18

8:55 am-8:00 am

2 stops16h 05m

Madrid Barajas

jue. 11/27

6:25 am-12:10 pm

1 stop12h 45m

$480

ChicagoMadrid

ORD - MAD

ORDMAD

Chicago O'Hare Intl

mié. 11/12

5:55 pm-4:40 pm

1 stop15h 45m

Madrid Barajas

mié. 11/19

5:55 am-8:05 pm

1 stop21h 10m

$480

ChicagoMadrid

ORD - MAD

ORDMAD

Chicago O'Hare Intl

mié. 11/12

5:55 pm-4:40 pm

1 stop15h 45m

Madrid Barajas

jue. 11/20

6:00 am-2:55 pm

2 stops15h 55m

$481

ChicagoMadrid

MDW - MAD

MDWMAD

Chicago Midway

vie. 12/5

1:05 pm-9:15 am

1 stop13h 10m

Madrid Barajas

jue. 12/11

11:15 am-11:47 pm

1 stop19h 32m

$488

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/4

Showing 1-10 of 42 results
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Compare providers for flights from Chicago to Madrid

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Chicago to Madrid in November.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars
AranGrantPrice Accuracy2 starsTrust Score*3 stars
OvagoPrice Accuracy2 starsTrust Score*2 stars
CheapflightsfaresPrice Accuracy3 starsTrust Score*2 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago-Madrid flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Chicago-Madrid flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Chicago-Madrid flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago-Madrid flights, Cheapflights users trust eDreams the most. eDreams has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago-Madrid flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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 October 31, 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, September is the cheapest month in which you can book a flight from Chicago to Madrid (average of $289). Flying from Chicago to Madrid in June is currently the most expensive (average of $641). 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 noviembre 6, 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 at noon, which can drop the price by up to 18% 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 Monday mornings when fares are most often at their lowest. Saturday mornings 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 noviembre 6, 2025.

The most flights from CHI to MAD are scheduled on a Monday (7 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (7 on average).

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 78% 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 $347.

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: 11h 10m.

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.

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

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 noviembre 6, 2025.
Peruse reviews from past customers who have flown with Finnair, American Airlines, and TAP AIR PORTUGAL 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.
Finnair
7.6
Good
1,335 reviews

Food

6.7

Comfort

7.4

Boarding

7.6

Overall

7.6

Crew

8.1

Entertainment

6.9

Reviews

1 / 20
4.0
Okay

Anonymous,Sep 2025

WAW - HEL

My flight to Europe was cancelled and rebooked. Bags got lost by FinnAir. Flight back home from Europe was cancelled the very next day after we landed. Zero compensation for these back to back cancellations on the exact same trip. Kayak doesn’t help with flight cancellation before trips says to contact trip protection only for trip protection to say it’s up to kayak. Don’t fly FinnAir.
Finnair
7.6
Good
1,335 reviews
Finnair
7.6
Good
1,335 reviews

Food

6.7

Comfort

7.4

Boarding

7.6

Overall

7.6

Crew

8.1

Entertainment

6.9

Reviews

1 / 20
4.0
Okay

Anonymous,Sep 2025

WAW - HEL

My flight to Europe was cancelled and rebooked. Bags got lost by FinnAir. Flight back home from Europe was cancelled the very next day after we landed. Zero compensation for these back to back cancellations on the exact same trip. Kayak doesn’t help with flight cancellation before trips says to contact trip protection only for trip protection to say it’s up to kayak. Don’t fly FinnAir.
American Airlines
7.2
Good
11,040 reviews
Finnair
7.6
Good
1,335 reviews

Food

6.7

Comfort

7.4

Boarding

7.6

Overall

7.6

Crew

8.1

Entertainment

6.9

Reviews

1 / 20
4.0
Okay

Anonymous,Sep 2025

WAW - HEL

My flight to Europe was cancelled and rebooked. Bags got lost by FinnAir. Flight back home from Europe was cancelled the very next day after we landed. Zero compensation for these back to back cancellations on the exact same trip. Kayak doesn’t help with flight cancellation before trips says to contact trip protection only for trip protection to say it’s up to kayak. Don’t fly FinnAir.
TAP AIR PORTUGAL
7.1
Good
2,048 reviews
Finnair
7.6
Good
1,335 reviews

Food

6.7

Comfort

7.4

Boarding

7.6

Overall

7.6

Crew

8.1

Entertainment

6.9

Reviews

1 / 20
4.0
Okay

Anonymous,Sep 2025

WAW - HEL

My flight to Europe was cancelled and rebooked. Bags got lost by FinnAir. Flight back home from Europe was cancelled the very next day after we landed. Zero compensation for these back to back cancellations on the exact same trip. Kayak doesn’t help with flight cancellation before trips says to contact trip protection only for trip protection to say it’s up to kayak. Don’t fly FinnAir.
Iberia
7.0
Good
3,007 reviews
Finnair
7.6
Good
1,335 reviews

Food

6.7

Comfort

7.4

Boarding

7.6

Overall

7.6

Crew

8.1

Entertainment

6.9

Reviews

1 / 20
4.0
Okay

Anonymous,Sep 2025

WAW - HEL

My flight to Europe was cancelled and rebooked. Bags got lost by FinnAir. Flight back home from Europe was cancelled the very next day after we landed. Zero compensation for these back to back cancellations on the exact same trip. Kayak doesn’t help with flight cancellation before trips says to contact trip protection only for trip protection to say it’s up to kayak. Don’t fly FinnAir.
British Airways
6.7
Okay
7,500 reviews
Finnair
7.6
Good
1,335 reviews

Food

6.7

Comfort

7.4

Boarding

7.6

Overall

7.6

Crew

8.1

Entertainment

6.9

Reviews

1 / 20
4.0
Okay

Anonymous,Sep 2025

WAW - HEL

My flight to Europe was cancelled and rebooked. Bags got lost by FinnAir. Flight back home from Europe was cancelled the very next day after we landed. Zero compensation for these back to back cancellations on the exact same trip. Kayak doesn’t help with flight cancellation before trips says to contact trip protection only for trip protection to say it’s up to kayak. Don’t fly FinnAir.

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 7 flights from Chicago to Barajas per day from 17 different airlines.

  • How long is the flight from Chicago to Madrid?

    Departing from Chicago to Madrid will take you 12h 30m. Chicago and Madrid are separated by a distance of 4188 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

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

    JetBlue, at $120, was found to be the cheapest airline from Chicago to Madrid.Alternate airlines to your destination round-trip include TAP AIR PORTUGAL and Finnair. You may be able to fly from Chicago to Madrid for 82% less than the average price by searching for these airlines.

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

    Consider American Airlines (62%), Finnair (62%) or Iberia (62%) 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 $1,237, our data indicates the cheapest price to be $414. The most popular route (Chicago O'Hare Intl - Madrid Barajas), is priced around $320.

  • 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.

  • 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 $19 per day to make their sightseeing more efficient.

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

    Flights departing from Chicago and landing in Madrid layover in New York 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, September is the cheapest month in which you can book a flight from Chicago to Madrid (average of $289). Flying from Chicago to Madrid in June is currently the most expensive (average of $641). 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
Getafe

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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 noviembre 6, 2025.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$120Average$203FlexibilityNo cancel feeOn-time62%
TAP AIR PORTUGALCheapest$288Average$525FlexibilityNo cancel feeOn-timeN/A
FinnairCheapest$364Average$632FlexibilityNo cancel feeOn-time76%
Air CanadaCheapest$366Average$647FlexibilityNo cancel feeOn-time67%
Scandinavian AirlinesCheapest$387Average$491FlexibilityNo cancel feeOn-time77%
United AirlinesCheapest$433Average$666FlexibilityNo cancel feeOn-time69%
British AirwaysCheapest$438Average$627FlexibilityNo cancel feeOn-time70%
IberiaCheapest$461Average$737FlexibilityNo cancel feeOn-time77%
Aer LingusCheapest$474Average$694FlexibilityNo cancel feeOn-timeN/A
LufthansaCheapest$479Average$855FlexibilityNo cancel feeOn-time76%

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