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 April , May 2026

26 Apr - 13 May $ 573.00
CHI
Chicago
TAP Portugal
1 STOPS
MAD
Madrid
MAD
Madrid
TAP Portugal
1 STOPS
CHI
Chicago
Pick dates
08 Apr - 03 May $ 726.00
CHI
Chicago
TAP Portugal
1 STOPS
MAD
Madrid
MAD
Madrid
TAP Portugal
1 STOPS
CHI
Chicago
Pick dates
06 Apr - 20 May $ 1,260.00
CHI
Chicago
Iberia Airlines
DIRECT
MAD
Madrid
MAD
Madrid
Iberia Airlines
DIRECT
CHI
Chicago
Pick dates

Last minute flights from Chicago to Madrid

19 Apr - 01 May $ 603.00
CHI
Chicago
TAP Portugal
1 STOPS
MAD
Madrid
MAD
Madrid
TAP Portugal
1 STOPS
CHI
Chicago
Pick dates
08 Apr - 01 May $ 646.00
CHI
Chicago
TAP Portugal
1 STOPS
MAD
Madrid
MAD
Madrid
TAP Portugal
1 STOPS
CHI
Chicago
Pick dates
14 Apr - 30 Apr $ 1,066.00
CHI
Chicago
Aer Lingus
DIRECT
MAD
Madrid
MAD
Madrid
Aer Lingus
DIRECT
CHI
Chicago
Pick dates

One-way flights to Madrid from Chicago

6:00 PM - 10:00 PM
TAP Portugal
1 Stops
23h 20m
CHI - MAD
$ 355
Kiwi
Pick dates
6:00 PM - 10:20 AM
TAP Portugal
1 Stops
11h 40m
CHI - MAD
$ 389
Kiwi
Pick dates
10:30 PM - 10:30 PM
Iberia Airlines
0 Stops
8h
CHI - MAD
$ 595
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.