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Cheap flights from Chicago (CHI) to Madrid (MAD)

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0 Children (2~11)
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How to find the cheapest flight from Chicago (CHI) to Madrid (MAD)

How to find the cheapest flight from Chicago (CHI) to Madrid (MAD)
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How to find the cheapest flight from Chicago (CHI) to Madrid (MAD)
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How to find the cheapest flight from Chicago (CHI) to Madrid (MAD)
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Cheap flights from Chicago to Madrid in November , December 2025

30 Nov - 09 Dec $ 495.00
CHI
Chicago
Finnair
DIRECT
MAD
Madrid
MAD
Madrid
Finnair
DIRECT
CHI
Chicago
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30 Nov - 07 Dec $ 669.00
CHI
Chicago
TAP Portugal
1 STOPS
MAD
Madrid
MAD
Madrid
TAP Portugal
1 STOPS
CHI
Chicago
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30 Nov - 02 Dec $ 1,433.00
CHI
Chicago
Finnair
DIRECT
MAD
Madrid
MAD
Madrid
Finnair
DIRECT
CHI
Chicago
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Last minute flights from Chicago to Madrid

27 Nov - 01 Dec $ 1,125.00
CHI
Chicago
Swiss International Air Lines
1 STOPS
MAD
Madrid
MAD
Madrid
Swiss International Air Lines
2 STOPS
CHI
Chicago
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28 Nov - 01 Dec $ 1,539.00
CHI
Chicago
Turkish Airlines
1 STOPS
MAD
Madrid
MAD
Madrid
Turkish Airlines
1 STOPS
CHI
Chicago
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28 Nov - 30 Nov $ 3,670.00
CHI
Chicago
Air France
DIRECT
MAD
Madrid
MAD
Madrid
Air France
1 STOPS
CHI
Chicago
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One-way flights to Madrid from Chicago

8:25 PM - 2:50 PM
TAP Portugal
1 Stops
13h 45m
CHI - MAD
$ 313
Kiwi
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8:15 PM - 11:45 AM
TAP Portugal
1 Stops
10h 50m
CHI - MAD
$ 320
Kiwi
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5:40 PM - 5:40 PM
Iberia Airlines
0 Stops
8h 10m
CHI - MAD
$ 415
Kiwi
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How to find the cheapest flight from Chicago (CHI) to Madrid (MAD)

Related info for your journey
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How to find the cheapest flight from Chicago (CHI) to Madrid (MAD)
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How to find the cheapest flight from Chicago (CHI) to Madrid (MAD)
Some placeholder content for the first accordion panel. This panel is shown by default, thanks to the .show class.