Cheap Flights to Cuenca del Guadarrama from $295 (2026/2027)

Wander Wisely with exceptional service, 24/7 supportOpens in a new window

Feel at ease with free flight cancellations within 24 hours of booking

Change your flight without a fee on select flights

Jet to one of Cuenca del Guadarrama's top cities

A historic building with multiple towers and a reflection in the water.

San Lorenzo de El Escorial

Flights
San Lorenzo de El Escorial
A person standing in front of a large mural depicting a historical battle scene.

El Escorial

Flights
El Escorial

How Much Does it Cost To Fly To Cuenca del Guadarrama?

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Fri, Nov 13 - Sat, Nov 21
JFK
John F. Kennedy Intl.
MAD
Adolfo Suárez Madrid-Barajas
$529 Roundtrip, found 18 hours ago
$529
Roundtrip
found 18 hours ago
Select TAP Portugal flight, departing Fri, Nov 13 from John F. Kennedy Intl. to Adolfo Suárez Madrid-Barajas, returning Sat, Nov 21, priced at $529 found 18 hours ago
Mon, Nov 16 - Mon, Nov 23
EWR
Newark Liberty Intl. Airport
MAD
Adolfo Suárez Madrid-Barajas
$530 Roundtrip, just found
$530
Roundtrip
just found
Select TAP Portugal flight, departing Mon, Nov 16 from Newark Liberty Intl. Airport to Adolfo Suárez Madrid-Barajas, returning Mon, Nov 23, priced at $530 just found
Thu, Dec 3 - Sun, Dec 6
IAD
Washington Dulles Intl.
MAD
Adolfo Suárez Madrid-Barajas
$551 Roundtrip, just found
$551
Roundtrip
just found
Select TAP Portugal flight, departing Thu, Dec 3 from Washington Dulles Intl. to Adolfo Suárez Madrid-Barajas, returning Sun, Dec 6, priced at $551 just found
Fri, Dec 4 - Sat, Dec 12
JFK
John F. Kennedy Intl.
MAD
Adolfo Suárez Madrid-Barajas
$579 Roundtrip, found 1 day ago
$579
Roundtrip
found 1 day ago
Select Scandinavian Airlines flight, departing Fri, Dec 4 from John F. Kennedy Intl. to Adolfo Suárez Madrid-Barajas, returning Sat, Dec 12, priced at $579 found 1 day ago
Thu, May 6 - Sun, May 23
JFK
John F. Kennedy Intl.
MAD
Adolfo Suárez Madrid-Barajas
$589 Roundtrip, found 3 days ago
$589
Roundtrip
found 3 days ago
Select Air Europa flight, departing Thu, May 6 from John F. Kennedy Intl. to Adolfo Suárez Madrid-Barajas, returning Sun, May 23, priced at $589 found 3 days ago
Mon, Feb 1 - Mon, Feb 22
MIA
Miami Intl.
MAD
Adolfo Suárez Madrid-Barajas
$591 Roundtrip, found 19 hours ago
$591
Roundtrip
found 19 hours ago
Select TAP Portugal flight, departing Mon, Feb 1 from Miami Intl. to Adolfo Suárez Madrid-Barajas, returning Mon, Feb 22, priced at $591 found 19 hours ago
Wed, Oct 7 - Thu, Oct 15
IAD
Washington Dulles Intl.
MAD
Adolfo Suárez Madrid-Barajas
$596 Roundtrip, found 1 day ago
$596
Roundtrip
found 1 day ago
Select Iberia flight, departing Wed, Oct 7 from Washington Dulles Intl. to Adolfo Suárez Madrid-Barajas, returning Thu, Oct 15, priced at $596 found 1 day ago
Sun, Jan 17 - Wed, Feb 3
JFK
John F. Kennedy Intl.
MAD
Adolfo Suárez Madrid-Barajas
$630 Roundtrip, found 16 hours ago
$630
Roundtrip
found 16 hours ago
Select ITA Airways flight, departing Sun, Jan 17 from John F. Kennedy Intl. to Adolfo Suárez Madrid-Barajas, returning Wed, Feb 3, priced at $630 found 16 hours ago
OriginDestinationTravel DatesFlights From*
LTNMadridNovember 19 to November 25$58
FCOMadridNovember 20 to November 29$67
FRAMadridOctober 28 to October 31$191
JFKMadridNovember 22 to December 8$529
LAXMadridOctober 23 to October 31$592
MIAMadridDecember 2 to December 9$621
SCLMadridDecember 1 to December 31$635
TLCMadridNovember 17 to December 1$868
LIMMadridNovember 23 to December 2$908
UIOMadridDecember 1 to January 21$979
*Prices include taxes and fees
OriginDestinationTravel DatesFlights From*
LTNMadridAugust 29 to September 10$196
FCOMadridAugust 29 to September 5$215
FRAMadridAugust 28 to August 31$370
LAXMadridAugust 30 to October 3$814
JFKMadridAugust 29 to September 8$977
MIAMadridAugust 28 to September 4$1,002
MEXMadridAugust 29 to September 12$1,247
SCLMadridAugust 29 to September 13$1,381
LIMMadridAugust 30 to September 5$1,566
UIOMadridAugust 28 to January 31$1,639
*Prices include taxes and fees

Best Cuenca del Guadarrama Flight and Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Hotel Exe Moncloa
4.0-star property

Hotel Exe Moncloa

Oct 5 - Oct 11

6 night stay

Chicago (ORD) to Madrid (MAD)

United • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $2,940, price is now $1,904 per person
$1,904
per person
found 1 day ago
Ikonik Gran Via
4.0-star property

Ikonik Gran Via

Oct 5 - Oct 11

6 night stay

Chicago (ORD) to Madrid (MAD)

United • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $3,250, price is now $2,062 per person
$2,062
per person
found 1 day ago
Hotel Pinar Plaza
4.0-star property

Hotel Pinar Plaza

Oct 5 - Oct 11

6 night stay

Chicago (ORD) to Madrid (MAD)

United • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $3,502, price is now $2,255 per person
$2,255
per person
found 1 day ago
Don't see what you're looking for?
See all available trips from Chicago to Cuenca del Guadarrama
View all trips

Travelers ❤️ These Cuenca del Guadarrama 🏨

Hotel101- Madrid

Hotel101- Madrid

4 out of 5
Av. de las Fuerzas Armadas, 328 Madrid
Book a stay at this business-friendly hotel in Madrid. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Bernabéu Stadium and El Retiro Park are located nearby.
9.4/10 Exceptional! (1,222 reviews)
"Very clean. Shuttle to airport."

Reviewed on Aug 21, 2026

Opens in a new windowHotel101- Madrid
Hotel Regina

Hotel Regina

4 out of 5
Alcala 19 Madrid Madrid
Book a stay at this business-friendly hotel in Madrid. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Gran Via and Puerta del Sol are located nearby.
Opens in a new windowHotel Regina
Hotel Riu Plaza España

Hotel Riu Plaza España

4 out of 5
C/ Gran Via, 84 Madrid
Book a stay at this business-friendly hotel in Madrid. Enjoy free WiFi, an outdoor pool, and 2 bars/lounges. Our guests praise the breakfast and the pool in our reviews. Popular attractions Royal Palace of Madrid and Gran Via are located nearby.
9.4/10 Exceptional! (5,192 reviews)
"Outstanding service. Great room. Awesome rooftop pool and bar. Great breakfast. Would stay again"

Reviewed on Aug 21, 2026

Opens in a new windowHotel Riu Plaza España
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
Hard Rock Hotel Madrid

Hard Rock Hotel Madrid

4.5 out of 5
Ronda de Atocha 17 Madrid
Book a stay at this luxury hotel in Madrid. Enjoy free WiFi, an outdoor pool, and 3 bars/lounges. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions El Retiro Park and Puerta del Sol are located nearby.
9.4/10 Exceptional! (2,874 reviews)
"We loved our stay at Hard Rock in Madrid. KEURIG,I m not getting his name right, but he was the 1st staff member we met and he was outstanding. All of the staff members were so kind and accommodating. .Enjoyed the pool and surroundings. We had dinner every night at Hard Rock. Food was delicious. ..."

Reviewed on Aug 21, 2026

Opens in a new windowHard Rock Hotel Madrid
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

How much is the cheapest flight to Cuenca del Guadarrama?
A roundtrip flight to Cuenca del Guadarrama cost as little as $58 during the last seven days. When you're ready to book, we'll help you land a great deal. This price was available on Travelocity for flights to Cuenca del Guadarrama departing within the next year. Prices and availability are subject to change. Additional terms apply.
What is the cheapest month to fly to Cuenca del Guadarrama?
Spend more of your money on great experiences rather than airline tickets by hopping on a plane to Cuenca del Guadarrama in November. This is the best-priced month to jet to this place based on Travelocity's direct return flight demand between January and December last year. Take a peek at our list of flights and get away from it all on the cheap.
How can I check my flight status to Cuenca del Guadarrama?
There are a couple of useful ways to track your flight status. You'll find all the necessary info in our "Trips" portal, which is located at the top right of our homepage. Log in or open an account in seconds — you'll then be able to view and amend your bookings whenever you want to. For those on the move, the Travelocity app can also help you check the status of your flight to Cuenca del Guadarrama, as well as share travel details with any members of your family flying with you.
How do I find the best deals on flights to Cuenca del Guadarrama?
It's always wise to book ahead of schedule, and if you can, avoid traveling during the busy tourist season. Another smart way to save is by clicking the "Flexible dates" box at the top of the page after searching for your flights. It's an easy way to compare prices for surrounding days. In the last seven days, the best price for a roundtrip flight to Cuenca del Guadarrama was $58. This price was available on Travelocity for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.
Why should I book my flight to Cuenca del Guadarrama with Travelocity?
Pack your suitcase and get ready for an epic trip with Travelocity. It's our mission to find you the best deals on cheap flights to Cuenca del Guadarrama. Whether you're seeking airfares with flexible cancellation policies or cheap family flights from budget airlines, we'll make it happen.
What are the most popular flight routes to Cuenca del Guadarrama?
As a sought-after destination for travelers, you'll find terrific connections to Cuenca del Guadarrama. Check out this sample of major routes:

  • Barcelona (BCN-Barcelona Intl.) to Adolfo Suarez Madrid-Barajas Airport (MAD) - 3,523 flights a month.
  • Lisbon (LIS-Humberto Delgado) to Adolfo Suarez Madrid-Barajas Airport (MAD) - 3,302 flights a month.
  • Palma de Mallorca (PMI) to Adolfo Suarez Madrid-Barajas Airport (MAD) - 2,912 flights a month.

How much is a flight to Cuenca del Guadarrama on average?
Roundtrip flights to Cuenca del Guadarrama cost between $58 and $1,639 in the last seven days. If you spot a ticket price that suits your budget, get in quick. Cheap deals don't last long! These prices were available on Travelocity for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.
How long is the average flight to Cuenca del Guadarrama?
The length of your direct flight to Cuenca del Guadarrama is dependent on your departure point. For a good idea of what to expect, here are the average journey times for a number of top routes to Cuenca del Guadarrama:

  • Barcelona (BCN-Barcelona Intl.) to Adolfo Suarez Madrid-Barajas Airport (MAD) - 1 hour and 29 minutes
  • Lisbon (LIS-Humberto Delgado) to Adolfo Suarez Madrid-Barajas Airport (MAD) - 1 hour and 28 minutes
  • Palma de Mallorca (PMI) to Adolfo Suarez Madrid-Barajas Airport (MAD) - 1 hour and 56 minutes

What can I expect on a flight to Cuenca del Guadarrama?
The flight time and whether you're traveling with a low-cost or full-service carrier play a major role. If you're searching for long-haul flights to Cuenca del Guadarrama, entertainment, food and drinks should be standard inclusions. After cheap flights for family vacations? Check out the fares with budget carriers. These airlines usually don't offer as many inclusions, or you'll need to pay an extra fee for them.