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 October , November 2026

24 Oct - 18 Nov $ 643.00
CHI
Chicago
TAP Portugal
1 STOPS
MAD
Madrid
MAD
Madrid
TAP Portugal
1 STOPS
CHI
Chicago
Pick dates
18 Oct - 18 Nov $ 725.00
CHI
Chicago
TAP Portugal
1 STOPS
MAD
Madrid
MAD
Madrid
TAP Portugal
1 STOPS
CHI
Chicago
Pick dates
26 Oct - 03 Nov $ 1,535.00
CHI
Chicago
Finnair
DIRECT
MAD
Madrid
MAD
Madrid
Finnair
DIRECT
CHI
Chicago
Pick dates

Last minute flights from Chicago to Madrid

22 Oct - 31 Oct $ 1,019.00
CHI
Chicago
KLM Royal Dutch Airlines
1 STOPS
MAD
Madrid
MAD
Madrid
KLM Royal Dutch Airlines
1 STOPS
CHI
Chicago
Pick dates
25 Oct - 01 Nov $ 1,050.00
CHI
Chicago
Turkish Airlines
1 STOPS
MAD
Madrid
MAD
Madrid
Turkish Airlines
1 STOPS
CHI
Chicago
Pick dates
19 Oct - 31 Oct $ 1,555.00
CHI
Chicago
Iberia Airlines
DIRECT
MAD
Madrid
MAD
Madrid
Iberia Airlines
DIRECT
CHI
Chicago
Pick dates

One-way flights to Madrid from Chicago

9:10 PM - 11:45 AM
TAP Portugal
1 Stops
10h 55m
CHI - MAD
$ 339
Kiwi
Pick dates
9:10 PM - 9:00 PM
TAP Portugal
1 Stops
20h 20m
CHI - MAD
$ 339
Kiwi
Pick dates
10:20 PM - 10:20 PM
Iberia Airlines
0 Stops
8h 10m
CHI - MAD
$ 462
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.