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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 May , June 2026

18 May - 10 Jun $ 1,048.00
CHI
Chicago
United Airlines
1 STOPS
MAD
Madrid
MAD
Madrid
United Airlines
1 STOPS
CHI
Chicago
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18 May - 04 Jun $ 1,083.00
CHI
Chicago
TAP Portugal
2 STOPS
MAD
Madrid
MAD
Madrid
TAP Portugal
1 STOPS
CHI
Chicago
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18 May - 18 Jun $ 1,737.00
CHI
Chicago
Aer Lingus
DIRECT
MAD
Madrid
MAD
Madrid
Aer Lingus
DIRECT
CHI
Chicago
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Last minute flights from Chicago to Madrid

24 May - 31 May $ 1,037.00
CHI
Chicago
TAP Portugal
2 STOPS
MAD
Madrid
MAD
Madrid
TAP Portugal
1 STOPS
CHI
Chicago
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27 May - 31 May $ 1,087.00
CHI
Chicago
TAP Portugal
2 STOPS
MAD
Madrid
MAD
Madrid
TAP Portugal
1 STOPS
CHI
Chicago
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18 May - 31 May $ 2,032.00
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

9:49 AM - 10:00 PM
TAP Portugal
2 Stops
31h 31m
CHI - MAD
$ 668
Kiwi
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4:55 PM - 4:55 PM
Iberia Airlines
0 Stops
8h 25m
CHI - MAD
$ 803
Kiwi
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10:40 PM - 10:40 PM
Iberia Airlines
0 Stops
7h 50m
CHI - MAD
$ 1,205
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.