Cheap flights from Chicago to Sierra de Guadarrama

View AU$274 flight on Mon, 28 Jul. 2025Opens in a new window

Popular airlines from Chicago to Sierra de Guadarrama

  • American Airlines

    American Airlines

  • Air France

    Air France

  • Finnair

    Finnair

  • British Airways

    British Airways

  • Aer Lingus

    Aer Lingus

  • KLM

    KLM

  • Lufthansa

    Lufthansa

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

Prices were available within the past 7 days for one-way flights and round trip tickets for the period specified. Prices and availability are subject to change. Additional terms apply.

TAP Portugal
Fri, 14 Nov. - Thu, 20 Nov.
ORD
Chicago
MAD
Madrid
AU$485 Return, found 9 hours ago
AU$485
Return
found 9 hours ago
Select TAP Portugal flight, departing Fri, 14 Nov. from Chicago to Madrid, returning Thu, 20 Nov., priced at AU$485 found 9 hours ago
United
Fri, 14 Nov. - Thu, 20 Nov.
ORD
Chicago
MAD
Madrid
AU$646 Return, found 9 hours ago
AU$646
Return
found 9 hours ago
Select United flight, departing Fri, 14 Nov. from Chicago to Madrid, returning Thu, 20 Nov., priced at AU$646 found 9 hours ago
Swiss International Air Lines
Fri, 14 Nov. - Thu, 20 Nov.
ORD
Chicago
MAD
Madrid
AU$695 Return, found 9 hours ago
AU$695
Return
found 9 hours ago
Select Swiss International Air Lines flight, departing Fri, 14 Nov. from Chicago to Madrid, returning Thu, 20 Nov., priced at AU$695 found 9 hours ago
Lufthansa
Fri, 14 Nov. - Thu, 20 Nov.
ORD
Chicago
MAD
Madrid
AU$703 Return, found 9 hours ago
AU$703
Return
found 9 hours ago
Select Lufthansa flight, departing Fri, 14 Nov. from Chicago to Madrid, returning Thu, 20 Nov., priced at AU$703 found 9 hours ago
Air France
Fri, 14 Nov. - Thu, 20 Nov.
ORD
Chicago
MAD
Madrid
AU$733 Return, found 9 hours ago
AU$733
Return
found 9 hours ago
Select Air France flight, departing Fri, 14 Nov. from Chicago to Madrid, returning Thu, 20 Nov., priced at AU$733 found 9 hours ago
Delta
Mon, 11 Aug. - Wed, 27 Aug.
ORD
Chicago
MAD
Madrid
AU$740 Return, found 2 days ago
AU$740
Return
found 2 days ago
Select Delta flight, departing Mon, 11 Aug. from Chicago to Madrid, returning Wed, 27 Aug., priced at AU$740 found 2 days ago

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

November is typically the cheapest month to fly

From AU$541 - AU$1,225 per traveller.

Graph displaying average flight prices per month

*Available to Expedia members.