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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 December 2025 , January 2026

30 Dec - 18 Jan $ 547.00
CHI
Chicago
Finnair
DIRECT
MAD
Madrid
MAD
Madrid
Finnair
DIRECT
CHI
Chicago
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27 Dec - 11 Jan $ 1,125.00
CHI
Chicago
TAP Portugal
1 STOPS
MAD
Madrid
MAD
Madrid
TAP Portugal
1 STOPS
CHI
Chicago
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25 Dec - 08 Jan $ 1,952.00
CHI
Chicago
Iberia Airlines
DIRECT
MAD
Madrid
MAD
Madrid
Iberia Airlines
DIRECT
CHI
Chicago
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Last minute flights from Chicago to Madrid

24 Dec - 31 Dec $ 1,181.00
CHI
Chicago
United Airlines
1 STOPS
MAD
Madrid
MAD
Madrid
United Airlines
1 STOPS
CHI
Chicago
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28 Dec - 31 Dec $ 1,183.00
CHI
Chicago
TAP Portugal
1 STOPS
MAD
Madrid
MAD
Madrid
TAP Portugal
1 STOPS
CHI
Chicago
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25 Dec - 31 Dec $ 2,116.00
CHI
Chicago
Iberia Airlines
DIRECT
MAD
Madrid
MAD
Madrid
Iberia Airlines
DIRECT
CHI
Chicago
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One-way flights to Madrid from Chicago

7:10 PM - 11:45 AM
TAP Portugal
1 Stops
11h 55m
CHI - MAD
$ 289
Kiwi
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7:05 AM - 6:45 PM
United Airlines
1 Stops
17h 55m
CHI - MAD
$ 503
Kiwi
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5:40 PM - 5:40 PM
Iberia Airlines
0 Stops
8h 10m
CHI - MAD
$ 528
Kiwi
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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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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.