Cheapest one-way flights from Chicago to Madrid in May from $407

Best time to book flights for Chicago (ORD) to Madrid (MAD) flights at AirHint

AirHint found the following cheapest one-way flights from Chicago (ORD) to Madrid (MAD) in May 2025 (see full year).

One-Way flights

28 May Spirit Airlines
11 May ITA Airways
14 May United
14 May British Airways direct
30 May Spirit Airlines
12 May Air France
20 May jetBlue
25 May Spirit Airlines
29 May Air Canada
21 May Spirit Airlines

Also check the deals for return flights from Chicago to Madrid in May.

Skyscanner

The deals are updated regularly. The prices may go up as tickets are purchased by other travellers. Only the cheapest flights are offered. Select a price to book and secure these cheap prices.

Book a cheap hotel in Madrid

Cheap car rent in Madrid