Flights to Sierra de Guadarrama from Chicago - ￥57,850

View ￥57,850 flight on Sun, Jan 4, 2026Opens in a new window

Popular airlines from Chicago to Sierra de Guadarrama

  • Peach

    Peach

  • Skymark Airlines

    Skymark Airlines

  • All Nippon Airways

    All Nippon Airways

  • Japan Airlines

    Japan Airlines

  • Jetstar Japan

    Jetstar Japan

  • Solaseed Air

    Solaseed Air

  • STARFLYER

    STARFLYER

  • Plan, book, fly with confidence

  • trending down icon

    Be in the know

    Get alerts if flight prices drop or rise*
  • bex rewards loyalty icon

    Book smarter

    Save up to 40% on select hotels after you book a flight*
  • payments icon

    Earn twice

    Earn your airline miles on top of our rewards
    Sign in

Cheap Flights from Chicago to Sierra de Guadarrama (CHI-MAD)

Prices were available within the past 7 days and start at ￥57,850 for one-way flights and ￥52,510 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

United
Tue, Oct 28 - Thu, Nov 6
ORD
Chicago
MAD
Madrid
￥52,510 Roundtrip, found 2 days ago
￥52,510
Roundtrip
found 2 days ago
Select United flight, departing Tue, Oct 28 from Chicago to Madrid, returning Thu, Nov 6, priced at ￥52,510 found 2 days ago
American Airlines
Mon, Nov 24 - Wed, Dec 3
ORD
Chicago
MAD
Madrid
￥52,570 Roundtrip, found 2 days ago
￥52,570
Roundtrip
found 2 days ago
Select American Airlines flight, departing Mon, Nov 24 from Chicago to Madrid, returning Wed, Dec 3, priced at ￥52,570 found 2 days ago
Air Canada
Mon, Nov 24 - Wed, Dec 3
ORD
Chicago
MAD
Madrid
￥52,670 Roundtrip, found 2 days ago
￥52,670
Roundtrip
found 2 days ago
Select Air Canada flight, departing Mon, Nov 24 from Chicago to Madrid, returning Wed, Dec 3, priced at ￥52,670 found 2 days ago
KLM
Mon, Nov 24 - Wed, Dec 3
ORD
Chicago
MAD
Madrid
￥63,090 Roundtrip, found 2 days ago
￥63,090
Roundtrip
found 2 days ago
Select KLM flight, departing Mon, Nov 24 from Chicago to Madrid, returning Wed, Dec 3, priced at ￥63,090 found 2 days ago
American Airlines
Mon, Aug 18 - Wed, Aug 27
ORD
Chicago
MAD
Madrid
￥64,910 Roundtrip, found 2 days ago
￥64,910
Roundtrip
found 2 days ago
Select American Airlines flight, departing Mon, Aug 18 from Chicago to Madrid, returning Wed, Aug 27, priced at ￥64,910 found 2 days ago
Delta
Mon, Aug 18 - Wed, Aug 27
ORD
Chicago
MAD
Madrid
￥65,730 Roundtrip, found 2 days ago
￥65,730
Roundtrip
found 2 days ago
Select Delta flight, departing Mon, Aug 18 from Chicago to Madrid, returning Wed, Aug 27, priced at ￥65,730 found 2 days ago

Find the cheapest month to fly from Chicago (CHI) to Madrid (MAD)

October is typically the cheapest month to fly

From ￥53,228 - ￥130,861 per traveler.

Graph displaying average flight prices per month

*Available to Expedia members.