HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Madrid

$307+ 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 4/19. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MAD
Apr 27 — May 41
Mon 4/27
Mon 5/4
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Chicago to Madrid with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.
Cheapflights Tip: The best prices from Chicago to Madrid Barajas are usually found in October or September, booked 60 days in advance, depart on a Wednesday or Tuesday and return on a Thursday

Cheap 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 March 28, 2026.

This Mytrip deal was found by Cheapflights users on 3/27. 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.
Wed 10/288:00 pm
ORD
-
MAD
1 stop12h 05m
TAP AIR PORTUGAL
Sun 11/157:40 am
MAD
-
ORD
1 stop14h 20m
TAP AIR PORTUGAL
Deal found 3/27$509
This oojo deal was found by Cheapflights users on 3/27. 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.
Sun 4/126:00 pm
ORD
-
MAD
1 stop20h 25m
TAP AIR PORTUGAL
Wed 4/227:40 am
MAD
-
ORD
1 stop15h 20m
TAP AIR PORTUGAL
Deal found 3/27$519
This Mytrip deal was found by Cheapflights users on 3/24. 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.
Sun 4/126:00 pm
ORD
-
MAD
1 stop23h 20m
TAP AIR PORTUGAL
Tue 4/218:10 pm
MAD
-
ORD
1 stop26h 50m
TAP AIR PORTUGAL
Deal found 3/24$521
This Justfly.com deal was found by Cheapflights users on 3/23. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/88:15 pm
ORD
-
MAD
1 stop13h 55m
TAP AIR PORTUGAL
Sun 11/157:40 am
MAD
-
ORD
1 stop14h 20m
TAP AIR PORTUGAL
Deal found 3/23$525
This Justfly.com deal was found by Cheapflights users on 3/27. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/309:10 pm
ORD
-
MAD
1 stop10h 55m
TAP AIR PORTUGAL
Fri 11/137:40 am
MAD
-
ORD
1 stop14h 50m
TAP AIR PORTUGAL
Deal found 3/27$526
This oojo deal was found by Cheapflights users on 3/25. 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.
Fri 11/68:10 pm
ORD
-
MAD
1 stop17h 10m
TAP AIR PORTUGAL
Sat 11/146:00 pm
MAD
-
ORD
1 stop28h 00m
TAP AIR PORTUGAL
Deal found 3/25$529
This Super.com deal was found by Cheapflights users on 3/24. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/126:00 pm
ORD
-
MAD
1 stop20h 25m
TAP AIR PORTUGAL
Sun 4/196:35 am
MAD
-
ORD
1 stop16h 25m
TAP AIR PORTUGAL
Deal found 3/24$530
This Delta deal was found by Cheapflights users on 3/24. 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.
Sun 4/126:00 am
MDW
-
MAD
1 stop23h 15m
Delta
Tue 4/216:00 am
MAD
-
MDW
2 stops17h 26m
Delta
Deal found 3/24$661
This Delta deal was found by Cheapflights users on 3/23. 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.
Sun 11/1510:35 am
MDW
-
MAD
1 stop15h 40m
Delta
Wed 11/256:00 am
MAD
-
MDW
2 stops19h 10m
Delta
Deal found 3/23$662
This Delta deal was found by Cheapflights users on 3/24. 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.
Mon 4/131:24 pm
MDW
-
MAD
2 stops13h 31m
Delta
Tue 4/216:00 am
MAD
-
MDW
2 stops19h 36m
Delta
Deal found 3/24$667
This Trip.com deal was found by Cheapflights users on 3/23. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/126:00 am
MDW
-
MAD
1 stop23h 15m
KLM
Tue 4/216:00 am
MAD
-
MDW
2 stops17h 26m
KLM
Deal found 3/23$692
This Air France deal was found by Cheapflights users on 3/23. 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 Air France is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/2712:52 pm
MDW
-
MAD
1 stop16h 23m
Air France
Mon 5/412:45 pm
MAD
-
MDW
1 stop16h 43m
Air France
Deal found 3/23$698

Find 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 March 28, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$519
(oojo)

One-way from

$307
(Kiwi.com)

Popular in

December

Cheapest in

October

Average price

$674

Good round-trip deal

$676 or less

Good one-way deal

$512 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. 5% potential increase in price ($43 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($28 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 2026
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 March 28, 2026.
Use the filters below to find and compare flights from Chicago to Madrid that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoMadrid

ORD - MAD

ORDMAD

Chicago O'Hare Intl

Sun 4/12

8:45 am-4:45 pm

2 stops25h 00m

Madrid Barajas

Sun 4/26

5:55 am-8:45 pm

2 stops21h 50m

$718

ChicagoMadrid

MDW - MAD

MDWMAD

Chicago Midway

Sat 4/11

1:10 pm-12:10 pm

2 stops16h 00m

Madrid Barajas

Sun 4/19

6:00 am-5:58 pm

2 stops18h 58m

$770

ChicagoMadrid

MDW - MAD

MDWMAD

Chicago Midway

Fri 4/24

12:52 pm-12:15 pm

1 stop16h 23m

Madrid Barajas

Fri 5/1

6:00 am-5:58 pm

2 stops18h 58m

$833

ChicagoMadrid

ORD - MAD

ORDMAD

Chicago O'Hare Intl

Tue 3/31

12:15 pm-11:20 am

2 stops16h 05m

Madrid Barajas

Sat 4/11

6:00 am-5:53 pm

2 stops18h 53m

$833

ChicagoMadrid

MDW - MAD

MDWMAD

Chicago Midway

Tue 4/28

12:52 pm-12:15 pm

1 stop16h 23m

Madrid Barajas

Tue 5/12

9:50 am-9:09 pm

1 stop18h 19m

$873

ChicagoMadrid

ORD - MAD

ORDMAD

Chicago O'Hare Intl

Sat 4/18

4:00 pm-8:05 am

2 stops33h 05m

Madrid Barajas

Tue 4/28

6:20 am-6:44 pm

2 stops19h 24m

$873

ChicagoMadrid

ORD - MAD

ORDMAD

Chicago O'Hare Intl

Sat 4/11

5:40 pm-3:35 pm

2 stops14h 55m

Madrid Barajas

Sun 4/19

10:25 am-7:52 pm

2 stops16h 27m

$881

ChicagoMadrid

ORD - MAD

ORDMAD

Chicago O'Hare Intl

Thu 4/2

11:00 am-8:05 am

2 stops14h 05m

Madrid Barajas

Thu 4/9

8:20 am-7:55 pm

1 stop18h 35m

$882

ChicagoMadrid

ORD - MAD

ORDMAD

Chicago O'Hare Intl

Mon 5/18

2:55 pm-7:30 pm

1 stop21h 35m

Madrid Barajas

Fri 5/29

8:25 am-2:55 pm

1 stop13h 30m

$884

ChicagoMadrid

MDW - MAD

MDWMAD

Chicago Midway

Sat 4/25

1:24 pm-12:15 pm

2 stops15h 51m

Madrid Barajas

Sat 5/2

6:00 am-6:36 pm

2 stops19h 36m

$888

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/24

Showing 1-10 of 39 resultsSorted by cheapest first
1
2
3
4

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 March.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
OvagoPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
AranGrantPrice Accuracy2 starsTrust Score*2 stars
MytripPrice Accuracy2 starsTrust Score*3 stars
CheapflightsfaresPrice Accuracy2 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 FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Madrid flight deals on Cheapflights vs. FlightHub >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 FlightHub the most. FlightHub 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 March 13, 2026.

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 37 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 $626). 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 March 28, 2026.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago to Madrid as you normally would.

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 75% 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 $343.

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 Toronto (YYZ) have the shortest average one-way travel time for 1-stop routes: 11h 20m.

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 Toronto (YYZ) offer the fastest connection on this route, with an average layover time of 1h 39m.

How often are flights from Chicago to Madrid delayed?

About 33% of weekly flights between Chicago and Madrid have experienced delays in the past year, with the average delay time being 153 minutes.

What is the most punctual flight time for Chicago to Madrid flights?

Historically, flights departing at night are less likely to be delayed, whereas flights leaving in the evening tend to experience delays more often.

What day of the week experiences the fewest flight delays on this route?

Saturday tends to have the lowest number of delays on this route, whereas Tuesday has historically faced a higher average of delays compared to other days of the week.

Which airline has the best punctuality record on Chicago to Madrid flights?

Over the last year, American Airlines have had the lowest number of delays on this route, with just 26% of flights being delayed.

The best insider tips for Chicago to Madrid flights

AI-powered summary based on content written by travel experts. AI can make mistakes.
Cheapflights partnered with top experts to bring you the best recommendations for your Chicago to Madrid trip
Our travel experts
Ramsey Qubein

Ramsey Qubein

Expert on ORD

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

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 March 28, 2026.
Peruse reviews from past customers who have flown with Finnair,American Airlines, andTAP 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
7.7
Good
1,374 reviews

Boarding

7.7

Overall

7.7

Crew

8.2

Comfort

7.5

Entertainment

6.9

Food

6.7

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
7.7
Good
1,374 reviews
Finnair
7.7
Good
1,374 reviews

Boarding

7.7

Overall

7.7

Crew

8.2

Comfort

7.5

Entertainment

6.9

Food

6.7

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
7.1
Good
11,519 reviews
Finnair
7.7
Good
1,374 reviews

Boarding

7.7

Overall

7.7

Crew

8.2

Comfort

7.5

Entertainment

6.9

Food

6.7

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
2,182 reviews
Finnair
7.7
Good
1,374 reviews

Boarding

7.7

Overall

7.7

Crew

8.2

Comfort

7.5

Entertainment

6.9

Food

6.7

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
3,157 reviews
Finnair
7.7
Good
1,374 reviews

Boarding

7.7

Overall

7.7

Crew

8.2

Comfort

7.5

Entertainment

6.9

Food

6.7

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
7,825 reviews
Finnair
7.7
Good
1,374 reviews

Boarding

7.7

Overall

7.7

Crew

8.2

Comfort

7.5

Entertainment

6.9

Food

6.7

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 2 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 16h. Chicago and Madrid are separated by a distance of 4187 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 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 $170. However, be on the lookout for offers from Scandinavian Airlines and Finnair, 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 Qatar Airways (69%), Alaska Airlines (64%) or Aer Lingus (64%) 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 $1,584, our data indicates the cheapest price to be $343. The most popular route (Chicago O'Hare Intl - Madrid Barajas), is priced around $519.

  • 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 $626). 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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 March 28, 2026.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$120Average$203FlexibilityNo cancel feeOn-time62%
TAP AIR PORTUGALCheapest$288Average$521FlexibilityNo cancel feeOn-timeN/A
FinnairCheapest$356Average$634FlexibilityNo cancel feeOn-time76%
Air CanadaCheapest$366Average$709FlexibilityNo cancel feeOn-time67%
Scandinavian AirlinesCheapest$387Average$515FlexibilityNo cancel feeOn-time77%
DeltaCheapest$393Average$627FlexibilityNo cancel feeOn-timeN/A
British AirwaysCheapest$424Average$649FlexibilityNo cancel feeOn-time70%
United AirlinesCheapest$435Average$686FlexibilityNo cancel feeOn-time69%
IberiaCheapest$438Average$724FlexibilityNo cancel feeOn-time77%
Aer LingusCheapest$474Average$713FlexibilityNo cancel feeOn-timeN/A

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.