Earn point on your loyalty program!arrow arc left

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

Know your dates, get live prices in seconds
airplane logo

pin logo

calendar
Departure
calendar backward
Return
airplane logo
1 Adults (11+)
0 Children (2~11)
0 Infants (0~2)
Save up to 31%
Book Flight + Hotel at the same time

How to find the cheapest flight from Chicago (CHI) to Madrid (MAD)

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.
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.
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.

Cheap flights from Chicago to Madrid in September , October 2026

27 Sep - 01 Oct $ 789.00
CHI
Chicago
TAP Portugal
1 STOPS
MAD
Madrid
MAD
Madrid
TAP Portugal
1 STOPS
CHI
Chicago
Pick dates
27 Sep - 01 Oct $ 937.00
CHI
Chicago
TAP Portugal
1 STOPS
MAD
Madrid
MAD
Madrid
TAP Portugal
1 STOPS
CHI
Chicago
Pick dates
30 Sep - 08 Oct $ 1,569.00
CHI
Chicago
Finnair
DIRECT
MAD
Madrid
MAD
Madrid
Finnair
DIRECT
CHI
Chicago
Pick dates

Last minute flights from Chicago to Madrid

27 Sep - 01 Oct $ 845.00
CHI
Chicago
TAP Portugal
1 STOPS
MAD
Madrid
MAD
Madrid
TAP Portugal
1 STOPS
CHI
Chicago
Pick dates
27 Sep - 01 Oct $ 845.00
CHI
Chicago
TAP Portugal
1 STOPS
MAD
Madrid
MAD
Madrid
TAP Portugal
1 STOPS
CHI
Chicago
Pick dates
27 Sep - 30 Sep $ 2,606.00
CHI
Chicago
Finnair
DIRECT
MAD
Madrid
MAD
Madrid
Finnair
DIRECT
CHI
Chicago
Pick dates

One-way flights to Madrid from Chicago

6:00 PM - 1:05 PM
TAP Portugal
1 Stops
14h 25m
CHI - MAD
$ 438
Kiwi
Pick dates
4:55 PM - 4:55 PM
Iberia Airlines
0 Stops
8h 25m
CHI - MAD
$ 462
Kiwi
Pick dates
10:15 PM - 10:15 PM
Iberia Airlines
0 Stops
8h 15m
CHI - MAD
$ 465
Kiwi
Pick dates

How to find the cheapest flight from Chicago (CHI) to Madrid (MAD)

Related info for your journey
Some placeholder content for the first accordion panel. This panel is shown by default, thanks to the .show class.
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.
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.